Historical Guided Tour

This is an online listing of numerous Old Saybrook historic homes and sites. The first 52 locations replicate the printed Self-Guided Tour, available as a walking or biking tour, from the train station to Saybrook Point; a collaboration between the Historical Society and the Chamber of Commerce. Additional historic homes, located all around Old Saybrook, have been added to this online version. The majority of these locations are private properties and not open to the visitors.

Click on the interactive Google map of the Guided Tour to follow along, find more information, and see images of each location. Below is a full list.

1. Railroad Station
   • In 1855, the land was sold to the New Haven and New London RR Co. A part of the present station was constructed at that time and the station took its present appearance c. 1870. The most notable architectural feature is the overhang of the roof.
2. North Main Station, Upper Cemetery
   • Laid out in 1797 by the proprietors of the town commons, includes the graves of veterans from the French and Indian War to the Korean War.
3. 14 Main Street, Ambrose Whittlesey House
   • This Georgian style house was the home of Capt. Ambrose Whittlesey (1761-1827). The Whittlesey family was involved in farming, the merchandise trade, and shipbuilding.
4. Route 1 and Main Street, Coulter House, “Monkey Farm”
   • An 1853 map shows this building as the house of H. Kirtland. The estate was sold to James Coulter in 1864. All indications are that the building has been used as an inn since 1859. It is currently the Monkey Farm restaurant.
5. 300 Main Street, The Katharine Hepburn Cultural Arts Center
   • This building was built in 1905 as a community theater, remodeled into the Town Hall in 1963, and restored back to its original use as a cultural arts center in 2009.
6. 302 Main Street, Town Hall & Town Green

   • This building, constructed in 1936, is on the site of a wooden schoolhouse which opened in 1892. It served as a school until 1981 and was transformed and enlarged in 2004 to house Town government and recreation facilities.

7. 336 Main Street, Grace Church
   • The church was constructed in 1872 and is in English Country style. The arches and flying buttresses are examples of Gothic characteristics, which lend it the look of a miniature medieval cathedral
8. 336 Main Street, Grace Church Rectory
   • The c. 1873 home is a copy of a house seen in England by Rev. Jesse Heald. Most notable are the Gothic window in the front dormer and the unusual woodwork adorning the front porch rail and columns.
9. 350 Main Street, The Old Saybrook Historical Society
   • The William Hart House, Hart House Public Heritage Gardens, and the Frank Stevenson Archives building are owned by the Old Saybrook Historical Society which uses them as headquarters, museums, collections, research, and various historical programs.
10. 366 Main Street, The First Church of Christ
    • The present Greek Revival building, constructed in 1840, is the fourth church building or meeting house of the Saybrook Congregational Church. The first two were at Saybrook Point and the third on the Trivet Green across the street. The sides of the church were built flat on the ground and then lifted by a team of twenty oxen and placed in deep troughs.
11. Main St. and Pennywise Ln, The Trivet Green
    • also known as South Green or Church Green, is owned by the First Church and includes the Lafayette Trail and other historic markers.
12. 323 Main Street, James Pharmacy
    • This building is most well known as the pharmacy owned by Miss Anna Louise James, the first Black woman licensed as a pharmacist in Connecticut. It originally stood next to the Humphrey Pratt Tavern and was moved to its current location about 1865.
13. 274 Main Street, Sheffield Building

    • This c. 1853 Sheffield Building housed Stokes Brothers Store, an original department store in the area. Amos Sheffield built this brick building. Restored ghosted signs for two local businesses, Stokes Brothers Grocery and James A. Crowley Real Estate, remain on the side of the building.

14. 530 Main Street, Millstone
    • This millstone is either from a circa 1780 wind mill built by Jeremiah Sheme of Long Island or stones moved to the “Neck” from one of William Lynde’s Oyster River tide mills around 1820.
15. Next to the firehouse, Postal Mile Marker
    • Benjamin Franklin, as the first Postmaster General, had stone markers placed along stagecoach roads showing miles to a central town. The marker on Main Street south of the firehouse is one of three remaining in Old Saybrook.
16. Across from the firehouse, Town Pump
    • In 2002 a replica of the old town pump was erected, including the 1900 STIA horse-watering trough donated by the Old Saybrook Historical Society. The original pump had a trough for horses and a well with a rotary crank with cups attached for people.
17. 15 Fenwick Street, Cypress Cemetery
    • Lion Gardner laid out the Ancient Bury Ground in 1636 on land long used for burials by Native Americans. Lady Fenwick’s grave was moved to the cemetery in 1870 due to the railroad construction at the Point.
18. 93 College Street, Yale Boulder
    • The Yale Boulder marks the site of the Collegiate School founded in 1701. The school moved to New Haven in 1716 and became Yale University.
19. Saybrook Point, Fort Saybrook

    • Within the park is a memorial to Lion Gardiner, a short trail to the riverbank and information stations that explain the history of the Pequot War and Fort Saybrook.

20. 100 Coulter Street Founders Memorial Park
    • The 17-acre Founders Memorial Park combines land donated to the Town by members of the Clarke family, descendants of one of the original settlers of the Saybrook Colony. The land was a town-owned former railroad right-of-way, and the now-closed town landfill.
21. 48 Main Street, Hefflon House
    • This c. 1800 ½ cape with additions has dentil molding, a dutch door, and 6 over 9 pane windows. It remained in the Hefflon family until the 1920s.
22. 50 Main Street, Burns and Young Store
    • The Burns and Young market, located in this 1905 building, was one of the major stops on the New London/New Haven Trolley.
23. 56 Main Street, Ingham House
    • This c. 1890 house was built for Horace Archer and was later the home of Robert Burns, who was associated with the Burns and Young Store. It is distinctive in its design with angled corners and a multihued roof.
24. 65 Main Street, Eihu Ingham House
    • This c. 1795 house is one of the few original buildings on Main Street remaining from the 18th century in the commercial section of town. It was built for Elihu Ingham (1783-1837) and was used as a residence until the 1960s.
25. 287 Main Street, Humphrey Pratt Tavern
    • This c. 1795 house is one of the few original buildings on Main Street remaining from the 18th century in the commercial section of town. It was a stage stop on the run between New Haven and Boston and served as the first Post Office. The ballroom in the ell has a spring floor to facilitate dancing.
26. 412 Main Street, Joseph Buckingham House
    • Long known as The Old Buckingham House, this c. 1671 house was once the home of Thomas Buckingham, one of Yale’s original founders.  It is believed to be the site of the first Yale commencement in 1702.
27. 322 Main Street, John Shipman House
    • John Shipman (1792-1857), a merchant and a veteran of the War of 1812, owned this c. 1836 house. Since he had no children of his own, he left the house to his nieces and nephews who sold it shortly after his death.
28. 325 Main Street, Deacon Timothy Pratt House
    • This c. 1745 house was the home of Timothy Pratt, Sr. (1716-1753), a carpenter and deacon in the Congregational Church. It is thought to have served as a private school in the 1890s and it was later known as Treadway House.
29. 334 Main Street, Samuel Hart Pratt House
    • This well-preserved 1870s house with a gable-end-orientation and a wraparound veranda was the home of Samuel Hart Pratt (1843-1924) and is known as the Chapman house named for Samuel’s daughter, Edith Pratt Chapman. It is owned today by Grace Church.
30. 341 Main Street, P. L. Shepard House
    • This building dates from the 1770s and was purchased in 1867 by Rev. Peter Shepard (1825-1912). He and his wife opened a boarding school here in 1865, naming it the Seabury Institute after the first U.S. Episcopal Bishop.
31. 365 Main Street, W.E. Clark House
    • This house appears on the 1874 map as the home of William E. Clark (1840-1900), the son of William J. Clark. The overhang of the roof and the exposed rafters in the overhang are a decided trademark of the stick style construction of that period.
32. 369 Main Street, W.J. Clark House
    • This c. 1840 house was built for William J. Clark (1812- 1889), by his brothers-in-law, Rufus Clark Denison, and Rufus Clark Shepard. In 1870 the remains of Lady Fenwick were taken to this house after being exhumed at Saybrook Point to make room for the railroad.
33. 381 Main Street, Justin B. Holman House
    • This house was built as the home of Justin B. Holman in 1871. Mr. Holman served as the conductor on the Valley Branch of the New York, New Haven, and Hartford Railroad for over thirty years, beginning with the first train to Saybrook Point on July 31, 1871.
34. 385 Main Street, George W. Denison House
    • George W. Denison (1839-1909) acquired the land from his uncle, John F. Bushnell, in 1872 and built the house around 1873. While replacing wiring in the central hallway in 2017 the owners found a worn 19th century shoe placed there to ward off evil spirits.
35. 395 Main Street, Samuel Hart House
    • Built c. 1773 by Samuel Hart, son of Rev. William Hart. The center chimney construction is typical of the colonial era. Some interior rooms have original paneled walls.
36. 404 Main Street, John Shipman House
    • A plaque identifies this as the home of John Shipman (1748-1817). The map drawn by Harriet Chapman Chesebrough shows a house with his name on this site in 1788. The architecture, exclusive of the dormer remodeling, indicates a c. 1687 construction.
37. 488 Main Street, Wiliam B. Tully House
    • This c. 1870 house was owned by William Buckingham Tully (1839-1880), the publisher of the Saybrook News. He donated several artifacts to the Historical Society, including the Cromwellian Sealskin Chair and the Gilliam Saybrook Chest located at the Gen. William Hart House.
38. 500 Main Street, Samuel Eliot House
    • Lore says this house was built c. 1737 by Samuel Eliot but records indicate it was built by his brother, Dr. Augustus Eliot. Sold to Capt. Samuel Lord in 1749, it remained in this family until 1890. Owners of the house include Capt. David Newell, a ship captain killed by slaves in the Cape Verde Islands in 1819.
39. 24 North Cove Road, Edgar Dickenson
    • When the house was built is uncertain although it appears on maps from 1709 and 1793. The house was purchased by Edgar Dickinson (1838-1912) in 1869 from his nephew and he lived there until his death. Richard Dickinson (1695-1749), Edgar’s great grandfather, bought the land in 1728.
40. 55 North Cove Road, Robert Bull House
    • Also known as “the House on the Bend,” it was built on land acquired by Robert Bull (1624- 1688) in the 1670s. It is the oldest house in the North Cove Historic District. Likely remodeled around 1740, as that is when the earliest gambrel roofs began to appear.
41. 70 North Cove Road, Capt. John Dolbeare House
    • This house was built by Captain John Dolbeare (1819-1888) around 1855. Captain Dolbeare was a fisherman and seined shad in the Spring. The house was enlarged and remodeled in 1931, at which time the two-story colonnade on the west gable end was most likely added.
42. 91 North Cove Road, John Ingraham House
    • The main block of the house is thought to have been built in 1734 by John Ingraham (1679- 1750). The house has later additions at its western end.
43. 100 North Cove Road, Asa Kirtland House
    • Asa Kirtland (1778-1861) built this house about 1805. Asa and his brother, John, sold to their younger brother, Bushnell, the land on which he built his house next door.
44. 110 North Cove Road, Bushnell Kirtland House
    • This house, built c. 1810, has a Federal-style central bay with a Palladian window and an elaborate entry. The house was built by Bushnell Kirtland, a shipbuilder. His brother, Asa Kirtland, built the house at 100 North Cove Road in 1805.
45. 122 North Cove Road, Capt. J. Ingraham House
    • This house was built c. 1810 as the home of Captain John Ingraham, a sea captain. The current Colonial Revival front portico was added when the house was renovated and restored in 1941.
46. 141 North Cove Road, John Bushnell House
    • The original house was built in 1790 by John Bushnell. It was owned by Edward Ingraham in the mid-19th century. The house burned in 1915 and was reconstructed by Edward’s wife, Amelia Ingraham.
47. 174 North Cove Road, Capt. W. Lynne House
    • Built in 1799 by Willoughby Lynde, a wealthy sea captain. Willoughby and his father, Samuel Lynde, farmed and traded with the West Indies.
48. 175 North Cove Road, Black Horse Tavern
    • This house was erected around 1712 by John Burrows. Known as the Black Horse Tavern, it served travelers as an inn for years and was a Customs House during the brief period when Saybrook was a port of entry on the Connecticut River.
49. 191 North Cove Road, Capt. G. Dickinson House
    • George Dickinson (1770-1857) was a ship master and at times resided in foreign ports as agent. At his death in 1857 he was the wealthiest man in town. The west end of the building contained a ship chandlery.
50. 200 North Cove Road, George Pratt House
    • Erected on the foundations of an older house which was burned by gunfire from British warships in 1812. George Pratt was the son of Humphrey Pratt and the husband of Sally Murdock, who was the niece of General William Hart’s wife, Esther.
51. 48 Cromwell Place, Capt. C. Williams House
    • Capt. Charles Williams (1808-1883), who built this Greek Revival house in 1842, was from a family of sea captains. His father was Captain Hamlin Williams, who owned a schooner and traded with the West Indies.
52. 70 College Street, Willard House
    • In l635 Sergeant Samuel Willard was dispatched by John Winthrop Jr. to take possession of the mouth of the Connecticut River and to erect buildings. His descendant, William Willard (1777-1869), built this brick house in 1837.
53. 33 Old Boston Post Road, Judge William Lynde House (1791)
    • William Lynde was a judge of probate and influential citizen of Old Saybrook. His house, located at 33 Old Boston Post Road, was built c. 1791.
54. 40 Old Boston Post Road, Acton Library (1873)
    • The original Acton Library building in Old Saybrook was erected in 1873 on land donated by Thomas Acton at the corner of Old Boston Post Road and Pennywise Lane. The Library was dedicated on July 4, 1874. Thomas C. Acton (1823-1898) was a New York City politician and Police Commissioner whose summer home in Old Saybrook was across the street from the library. Begun as a subscription library, it became a public library in 1904. A new Acton Library was constructed in 1967 at 60 Old Boston Post Road. The former library, at 40 Old Boston Post Road, was bought from the town by architect Robert Wendler in 1970. He converted it into a single-family residence.
55. 45 Old Boston Post Road, Capt. William Clark House (1790)
    • The Captain William Clark House at 45 Old Boston Post Road in Old Saybrook is thought to have been built c. 1780/1790, with later alterations made in the Greek Revival style in the 1850s when it was acquired by Thomas C. Acton. The house would become known as Acton Place. T. C. Acton (1823-1898) was a politician and reformer in New York City and was the first person to be appointed president of the city’s Board of Police Commissioners. During the early stages of the New York City Draft Riots in 1863, after police superintendent John A. Kennedy had been incapacitated due to a beating by the angry mob, Acton took active charge of police forces in Manhattan. This tense experience placed a strain on his health and after the Riots Acton took a five year leave of absence from the NYPD. He later served as Assistant U. S. Treasurer, a position he eventually left to establish the Bank of New Amsterdam. In 1896 Acton moved to his summer home in Old Saybrook where he died on May 1, 1898. The house remained in the Acton family well into the twentieth century.
56. 52 Old Boston Post Road, Masonic Hall, Old Saybrook (1830)

    • The building at 52 Old Post Road in Old Saybrook was built in the 1830s and began as a one-story carpenters’ workshop used by the builders of the First Church of Christ on Main Street. When the church was completed, the building was moved from the town green to a site on Old Boston Post Road and a second story was added. For a time, Frederick Kirtland had a shoe store in the building. In its second location, the building stood east of where Thomas C. Acton would build a library in 1873. Acton, who had bought the house across the street, also acquired the former church workshop in 1870 and at some point thereafter it was moved to its current location west of the library. In 1903, Acton rented the building to the Masons of Siloam Lodge No. 32. In December, 1907 he sold the building and it was formally purchased by the Masons in February, 1908. The facade of the Masonic Hall has been altered over the years. In the early twentieth century, there was little decoration, but at some point afterwards it was elaborately ornamented with pilasters, dentil moldings and a fan light in the gable. Most of this ornamentation has since been removed (the street number was also changed from 50 to 52).

57. 83 Old Boston Post Road

    • The Greek Revival house at 83 Old Boston Post Road in Old Saybrook was built in 1847 by Rufus C. Shepard, a deacon of the Congregational Church who served as County Commissioner and Representative in the state legislature.

58. 220 Middlesex Turnpike, Piontkowski House (1880)

    • The exterior of the vacant house at 220 Middlesex Turnpike in Old Saybrook was used as a location for the 1971 horror film, Let’s Scare Jessica to Death. Interior shots were filmed about a mile away at the E.E. Dickinson House in Essex. The house in Old Saybrook was owned, then as now, by the Piontkowski family. The house was built in the 1880s as a farm house. By the turn of the century an owner had added the elaborate tower and named it “Fairview Farm.” J.P. Newton, a Hartford market-owner, purchased it from the Denison family in 1889. He set up an extensive farming operation to supply his markets. By 1930 the property was acquired by Fred Pointkowski (1893-1968) and his wife Bertha Kruck Pointkowski (1903-1979). It was inherited by their son, Carl F. Piontkowski (1931-2013).

59. 680 Middlesex Turnpike, William Parker House (1646)

    • The sign on the Parker House at 680 Middlesex Turnpike in Old Saybrook gives it the date of 1646. The National Register of Historic Places nomination for the house gives a date of 1679. In either case, it is one of the oldest houses in Connecticut. It was built by William Parker (1645-1725). Born in Hartford, Parker settled in Saybrook. As described in Family Records: Parker-Pond-Peck (1892), by Edwin Pond Parker: Dea. William Parker was a leading citizen, and very prominent in church and state. He is said to have represented Saybrook as Deputy to the General Court in more sessions than any other person, excepting only Robert Chapman. He was Sergeant in Train-band as early as 1672, and in 1678-9 the town voted him five acres of land for services “out of the town” in the Indian wars. He was elected Deacon before 1687, and probably continued in that office until his death. He was a lay member of the Saybrook Synod of 1705 that framed the “Saybrook Platform” for the churches of Connecticut. The house descended in the same family into the 1960s.

60. 1146 Boston Post Road, William Chalker House (1803)

    • The house at 1146 Boston Post Road in Old Saybrook was built c. 1800-1803 for William Chalker. It originally stood on the opposite side of the street but was moved and an addition built when the road was straightened later on in the nineteenth century. Around that time the house was acquired by Daniel C. Spencer. A wealthy merchant, Daniel Chapman Spencer (1823-1906) started his business career as a store clerk and then was a traveling salesman with a stock of goods carried in a peddler’s wagon. He then worked for Moulton, Plympton, Williams & Co., one of the leading wholesale dry goods firms of New York. After that company went out of business he moved on to Claflin, Mellen & Co. in New York, at the time the second largest dry goods store in the United States and soon to become the largest. He ran the company‘s notion department for thirteen years, until he broke down from the strain and decided to retire on January 1, 1868. He chose to retire to his hometown of Old Saybrook.  Spencer owned greenhouses across the street from the Chalker House. He was also involved in the development of the Borough of Fenwick, including the building of the hotel known as Fenwick Hall.  The Chalker-Spencer House was altered around 1880 when the original roof was replaced by a Mansard roof. It was later used as a boarding house.

61. 1445 Boston Post Road, Bushnell Farm (1678)

    • One of the five oldest houses in Connecticut is the Bushnell Farm house at 1445 Boston Post Road in Old Saybrook. It began as a two room, one story, thatch roofed post and beam house built by the Elder Joshua Bushnell. It is listed in the National Register of Historic Places as the Elisha Bushnell House and J. Frederick Kelly, in his classic Early Domestic Architecture of Connecticut (1924), calls it the Older Bushnell House. The house was expanded over the two centuries that the Bushnell family owned it. The property has a number of outbuildings, including an early eighteenth-century barn, a loom house. Maintained as a private property by Sherry and Herb Clark of Essex, who allow the property to be opened to schools, historical societies and other local non-profit organizations.

62. 21 Bridge Street, WIlliam Vars House, “Three Stories”

    • The Italianate house at 21 Bridge Street on Saybrook Point in Old Saybrook was built in 1892 as a home for the prominent engineer William Vars. In the twentieth century it was the home of Mary Clark. By the late 1990s the house had become dilapidated, but it has been refurbished to become an eight-room guesthouse. Called “Three Stories,” it is owned by of Saybrook Point Inn & Spa, whose main building is located just across the street. The guesthouse, which remains true to the architecture and interior design of the period, opened in May, 2014.

63. 19 Bridge Street, Tall Tales House

    • Tall Tales is a detailed renovation of an Italianate historic home which was originally built as a private residence in the 1850s. It is owned by Saybrook Point Resort & Marina. Tall Tales celebrates some of the remarkable people of Old Saybrook who influenced the town’s character over the past almost 400 years with rooms dedicated to Lt. Lion Gardner, Adrien Block, Lady Fenwick, General William Hart, early educator Maria Sanford and former First Selectwoman, Barbara Maynard.

64. 170 Old Post Road, Bushnell-Dickinson House (1790)

    • At 170 Old Post Road in Old Saybrook is a gambrel-roofed house built c. 1790 (before 1803) by Phineas Bushnell (1718-1803), shortly after he married his second wife, Hepsibah Lewis of Killingworth, in 1789. The house passed to his son Samuel Bushnell (1748-1828), who had married Hepzibah Pratt in 1775. Their daughter, Hepzibah (1776-1818), married Samuel Dickinson (1774-1861) in 1796. The house was later owned by their son, John Seabury Dickinson (1807-1879) and then by his son, John S. Dickinson (1846-1922), who served as a Town Selectman, was president of the Saybrook Musical and Dramatic Club and was a founder and first president of a literary society known as the Crackers and Cheese Club. The house remained in the Dickinson family until 1934. Renovated in 1958, the house was recently listed on the National Register of Historic Places.

65. 64 Cromwell Place, Samuel Hart, Jr. House (1813)

    • In 1813, Samuel Hart Jr. built the Federal-style house at the current address of 64 Cromwell Place in the North Cove Historic District in Old Saybrook. Capt. Samuel Doty, a mariner in the West Indies trade and a shipbuilder, had an earlier house on the site. It was torn down to built the current house.

66. 4 Agawam Avenue, Morgan-Williams-Francis Cottage (1885)

    • At 4 Agawam Avenue in the Borough of Fenwick in Old Saybrook is a Queen Anne cottage that was once located on the waterfront in Fenwick. It was built in 1885 for Henry P. Morgan of Brooklyn, who owned a large dry goods business, and was moved to its current location (4 Agawam Avenue) around 1901 by Ernest Williams, who was in the building supply business. His daughter Dorothy married Everett Francis of Middletownn. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), page 170.

67. 8 Agawam Avenue, James B. Moore Cottage (1890)

    • The cottage at 8 Agawam Avenue was constructed in 1890 by local builder George Sheffield for James B. Moore. Like his father, George W. Moore, James B. Moore acquired his wealth by brokering mortgages in the southern and western states after the Civil War. For the past five years, he and his family had spent their summers staying at Fenwick Hall, but in 1890 he was furious to find the hotel fully booked for the entire summer. He proceed to build his own Fenwick cottage in just six weeks. Designing it himself without an architect, he had no halls built on the second floor and hardly any closets in the entire house! The cottage was finally sold out of the family by James Moore, Jr. in 1946. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 166-169.

68. 30 Agawam Avenue, St. Mary’s-by-the-Sea (1886)

    • The Borough of Fenwick has long had its own house of worship, St. Mary’s-by-the-Sea. Religious services for the Fenwick summer community were initially led by Rev. Francis Goodwin in his own home. A leader of both Hartford and Fenwick society and an amateur architect, Rev. Francis Goodwin (1839-1923) championed the development of more parks in Hartford as the city’s first commissioner of parks. In 1883, Rev. Goodwin designed and built a small chapel on his property for Sunday worship. By 1886, the chapel was too small to accommodate the number of worshipers, so it was moved to its current location (30 Agawam Avenue) and enlarged with additional pews and a bell tower. St. Mary’s-by-the-Sea is a Shingle style structure, as are so many of the Fenwick summer cottages. You can read more about St. Mary’s-by-the-Sea in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 37-49.

69. 41 Agawam Avenue, Bradin-Robinson Cottage (1885)

    • The summer cottage at 41 Agawam Avenue in the Borough of Fenwick in Old Saybrook was built c. 1885 for Rev. James Watson Bradin and his wife Eliza Ann Jackson Bradin. A graduate of Berkeley Divinity School, then located in his wife’s hometown of Middletown, Rev. Bradin become rector of St. John’s Episcopal Church in Hartford in 1882. At that time the church was located on Main Street, but in 1907 the church left its original home, which was demolished to make way for the Morgan Memorial of the Wadsworth Atheneum. The current St. John’s Episcopal Church, on Farmington Avenue in West Hartford, was consecrated on June 9, 1909. Rev. Bradin continued as rector of the church until 1918. He and his wife had seven children. They named their Fenwick cottage the Kennel. The cottage passed to the couple’s daughters. In 1951 the cottage was acquired by Henry S. Robinson, Jr., a lawyer with the firm of Robinson, Robinson and Cole of Hartford, and his wife Constance Brainard Robinson. She was the daughter of Morgan Bulkeley Brainard, president of Aetna Life Insurance, and granddaughter of Leverett Brainard and Morgan G. Bulkeley. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 148-150.

70. 16 Fenwick Avenue, Skinner-Greene-Dickinson Cottage (1880)

    • The summer cottage at 16 Fenwick Avenue in the Borough of Fenwick in Old Saybrook was built in 1880 by Ebenezer Roberts of Hartford for his daughter Florence Clarissa and her new husband, Colonel William Converse Skinner. Ebenezer Roberts was a partner with the Keney Brothers of Hartford in in their wholesale grocery business.  Col. Skinner died in 1922, but around 1885 he had already sold his Fenwick home to Colonel Jacob Greene of Hartford, president of the Connecticut Mutual Life Insurance Company. Jacob Lyman Greene grew up in Maine, but later went to the University of Michigan and became a lawyer. He later served in the Civil War, eventually becoming a Colonel and the Adjutant-General of General George Armstrong Custer. He and Custer became best friends and Greene was best man at Custer’s wedding in 1864 to Libbie Bacon, who was friends with Greene’s wife, Nettie Humphrey. After the War, Col. Greene went to work for the Berkshire Life Insurance Company. In 1870 he moved to Hartford to work for Connecticut Mutual, eventually becoming the company’s president. When President Theodore Roosevelt visited Hartford in 1902 and became the first president to ride in an automobile in public, it was Col. Greene was sat next to him as chairman of Hartford Citizen’s Committee.

      The cottage in Fenwick later passed through other owners. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 64-67. By the time that book was published the cottage was owned by the Dickinson family and is referred to as the Dickinson Cottage. The illustration of the cottage on page 64 of the book reveals that it has been much altered in the last forty years. A number of dormer windows, a balcony, a front porch and sun room have been added and the house house has been given shingled siding to match the many other shingle style houses in Fenwick. I do not know if these are restorations to an earlier appearance the house may have had or new innovations.

71. 20 Fenwick Avenue, Riversea Inn (1885)

    • Fenwick Hall burned in 1916, but its functions were taken over by the Riversea Inn, a Colonial Revival building at 20 Fenwick Avenue. The Riversea Inn had been built as a residence in 1885 and was remodeled into its present appearance around 1910. Since the 1950s, the building has again been a residence. You can read more about the Riversea Inn in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 67-75.

72. 22 Fenwick Avenue, Hollister-Day Cottage (1872)

    • One of the many lost homes of Hartford is the Barnabas Deane House, which once stood on Grove Street. Barnabas was the brother of Silas Deane of Wethersfield and he is said to built the house on instructions from his famous brother who ended up never returning from Europe to live in it. The house was later home to Nelson Hollister and then was occupied by The Open Hearth. While the Deane House was torn down in the 1920s to make room for a parking lot for the Hartford Club, another home owned by Mr. Hollister, who was a prominent businessman and the first treasurer of the Connecticut Valley Railroad, survives in the Borough of Fenwick in Old Saybrook. Located at 22 Fenwick Avenue, it was built by Hollister in 1872, making it one of the oldest cottages to be constructed in the Fenwick summer colony. In 1888, Hollister’s daughter sold the house to George H. Day of Hartford. Day made many additions to the house, but not always with a concern for aesthetic matters: he once built a second floor lavatory with exposed plumbing running down the house’s exterior! After c. 1917, the cottage served as an annex to the neighboring Riversea Inn. In 1949 it became a private residence again when it was sold to Mr. and Mrs. Samuel Jones, who were the first to make the cottage habitable year-round. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 76-78.

73. 26 Fenwick Avenue, William Patton Cottage (1872)

    • The summer cottage at 26 Fenwick Avenue in the Borough of Fenwick in Old Saybrook was built in 1872 by William Patton of Springfield. One of the first three cottages to be constructed in the borough, it originally stood on the site of the Mary Brace Collins Cottage at 28 Fenwick Avenue. Patton moved his cottage across the street in 1887. In the 1890s the cottage was owned by Richard Crocker, known as “Boss Crocker,” who was a leader of New York City’s Tammany Hall. In 1899 the cottage was bought by Leonard D. Fisk of Hartford, who remodeled it extensively. Fisk married Genevieve (Jennie) B. Judd, daughter Henry C. Judd, wool merchant and partner in the firm of Judd & Root. Fisk was one of two inheritors of the business of his grandfather, Leonard Daniels, who had a successful flower mill on the Park River in Hartford and was one of the city’s prominent citizens. In 1912 the Fisk family sold their cottage to William Waldo Hyde, a lawyer. It was sold by his widow in 1923. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 80-83.

74. 28 Fenwick Avenue, Mary Brace Collins Cottage (1887)

    • The summer “cottage” at 28 Fenwick Avenue in the Borough of Fenwick in Old Saybrook was built in 1887 for Mary Brace Collins, who lived at a now demolished house at 1010 Asylum Avenue in Hartford. Her father was Thomas K. Brace, first president of the Aetna Fire Insurance Company, and her husband was Atwood Collins, who became president of the Security Trust Company in 1896. The company later merged with the Hartford-Aetna National Bank in 1927 to form the Hartford National Bank and Trust Company. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 84-87.

75. 30 Fenwick Avenue, Leverett Brained Cottage (1871)

    • Leverett Brainard (1828-1902) purchased one of the original Fenwick lots in 1871, but he and his wife, Mary Jerusha Bulkeley (sister of Morgan G. Bulkeley) did not immediately undertake the building of a summer cottage. In 1877, Brainard acquired a Fenwick cottage that had been built circa 1871 by J.A. Eldridge of Springfield and had it moved to his own lot and remodeled to suit his needs. Over the years, as the family expanded, they added new rooms to the cottage, which came to bear little resemblance to its original appearance. Leverett Brainard, who lived on Washington Street in Hartford, was born in Colchester and attended Bacon Academy. He moved to Hartford in 1853 to work for the City Fire Insurance Company. He eventually became the president of The Case, Lockwood & Brainard Company, which was one of the largest publishing companies in New England. As his obituary in the New England Stationer and Printer (Vol. XVI. No. 5, August 1902) stated, Brainard was “one of Hartford’s most prominent citizens, and closely identified with the commercial progress of Hartford, Conn., for nearly half a century.” The house passed to the Brainard’s son, Newton C. Brainard, who left it to his nephew, his sister Edith’s son, Frank Kelso Davis. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 91-99.

76. 10 Mohegan Avenue, Katharine Hepburn House (1939)

    • The actress Katharine Hepburn (1907–2003) had long-standing connections with the Borough of Fenwick in Old Saybrook. Her parents, Dr. Thomas Norval Hepburn and Katharine Houghton Hepburn, who lived in Hartford, began spending their summers there in 1912. After the family’s original wooden Shingle-style cottage on Long Island Sound was swept out to sea in the hurricane of 1938, they built a new one of brick based on a design the family had modeled out of blocks and dominoes. The house, which covers about 8,000 square feet, was a frequent retreat for the actress, who eventually moved there to spend her final years. In the 1930s and 1940s, Howard Hughes would land his seaplane in the Sound, right in front of the Hepburn home. Katharine Hepburn shared the house with her brother, the playwright Richard Hepburn, who died in 2000. After Katharine Hepburn passed away in 2003, the house was acquired by the major New York City developer, Frank J. Sciame, Jr., who completely renovated the house in 2005 and put it up for sale. You can read more about the Hepburn “cottage” in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 171-179.

77. 20 Nibang Avenue, Westbrook-Gengras Cottage (1928)
    • The substantial waterfront summer cottage at 20 Nibang Avenue in the Borough of Fenwick in Old Saybrook was built on a lot acquired in 1928 by Frances Dunham Westbrook and her husband, Stillman Westbrook, Sr. (1888-1943), a senior vice-president at the Aetna Life Insurance Company who oversaw the construction of the Aetna Building on Farmington Avenue in Hartford. He was also the first chairman of the Hartford Housing Authority and Westbrook Village, a housing project that is currently being redeveloped, was named in his honor. In 1948, the cottage was acquired and remodeled by E. Clayton Gengras (1908-1983), who also acquired the Riversea Inn and other properties in the borough. Gengras founded Gengras Motor Cars, which he developed into one of the largest car dealerships in the nation. In recent years, the house has had new owners. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 58-61.
78. 5 Pettipaug Avenue, Morgan G. Bulkeley Cottage (1899)

    • Perhaps the most impressive of the Shingle-style summer houses in the Borough of Fenwick (pdf) in Old Saybrook is the one built in 1900 for Morgan Gardner Bulkeley. A legendary politician, Morgan G. Bulkeley was a four-term mayor of Hartford, 54th Governor of Connecticut (1889-1893), U.S. Senator, first president of Baseball’s National League and the third president of the Aetna Life Insurance Company for 43 years. Bulkeley lived on Washington Street in Hartford and was one of the leaders of the summer community of Fenwick, In 1899 he commissioned the Hartford architect, W.E. Becker to design his summer cottage at 5 Pettipaug Avenue in Fenwick. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 99-108.

79. 6 Pettipaug Avenue, Mrs. J.H.K. Davis Cottage (1913)

    • Edith Brainard Davis spent 95 summers in the Borough of Fenwick (pdf) in Old Saybrook. She was the daughter of Leverett Brainard, president of the Case, Lockwood & Brainard Company of Hartford, and Mary Bulkeley Brainard, who was the sister of Morgan G. Bulkeley. In 1907, Edith Hollister Brainard married John Henry Kelso Davis, who worked at Case, Lockwood & Brainard. The couple continued to summer at the Leverett Brainard Cottage in Fenwick until they hired the builder George Sheffield of Old Saybrook to erect their own cottage at 6 Pettipaug Avenue in 1913. Two picture windows on the ground floor facing Long Island Sound were added to the Davis Cottage in 1930 by her sons as a gift to Mrs. Davis. The cottage is now owned by E. C. Gengras, Jr. of the Gengras Auto Group. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 159-162.

80. 9 Pettipaug Avenue, Barbour-Cooper-Jensen Cottage (1905)

    • The summer cottage at 9 Pettipaug Avenue in the Borough of Fenwick in Old Saybrook has been described as a gem that is “particularly illustrative of shingle style architecture” (by Christopher Little in “A Summer Place,” Places, Vol. 1, No. 3, 1984). It was built in 1905 by Lucius B. Barbour (1878-1934) of Hartford (whose 1865 house on Washington Street still survives). Their daughter Alice was a childhood friend of Katharine Hepburn. In 1953, after the death of Barbour’s widow Charlotte Cordelia Hilliard Barbour, the cottage was sold to Richard F. Cooper and in 1961 it was sold again to Oliver Jensen (1914-2005), a co-founder of American Heritage Magazine. He was also one of the founders and the chief visionary for the 1971 revival of the Connecticut Valley Railroad (today part of the Essex Steam Train and Riverboat attraction). You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 110-114.

81. 10 Pettipaug Avenue, William H. Bulkeley Cottage (1886)

    • The summer cottage at 10 Pettipaug Avenue in the Borough of Fenwick was built in 1886 by William H. Bulkeley and was originally located at the site of the cottage of the cottage at 9 Pettipaug Avenue. William H. Bulkeley, (1840-1902) was the brother of Morgan G. Bulkeley. Before his death, William Bulkeley sold his cottage to his brother Morgan who sold it in 1905 to Lucius Barbour, who moved it to its current site to make way for his own larger cottage. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 156-159.

82. 11 Pettipaug Avenue, Hall-Wilson Cottage (1910)

    • The summer cottage at 11 Pettipaug Avenue in the Borough of Fenwick in Old Saybrook was built in 1910 for the Hall and Wilson families. It was erected on what had previously been the site of the 1885 cottage of Henry Morgan. That cottage was long rented by John Henry Hall and his family. Hall was one of the family that owned the Portland brownstone quarries and was a president of Colt Firearms. The Halls purchased the Morgan Cottage in 1901 and sold it to Ernest Wilson, who moved it to its current address at 4 Agawam Avenue. The Halls then built the current cottage, which was later owned by their grandson, John C. Wilson, Jr. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 114-115.

83. 12 Pettipaug Avenue, Giraud-Bulkeley Cottage (1881)

    • In 1881 a summer cottage in the Borough of Fenwick in Old Saybrook was built by Hariette Fenwick Jackson Giraud (1830-1923) of Middletown. In 1899, the cottage was moved back from Long Island Sound to Pettipaug Avenue by Morgan G. Bulkeley to make way for his new and impressive cottage. The former Giraud Cottage was moved again, this time one lot west, in 1913 to make way for the Davis Cottage. Bulkeley gave the Giraud Cottage, now 12 Pettipaug Avenue, to his son, Morgan Jr. (1885-1926), in 1919 and it was then passed to his widow, Ruth Collins Bulkeley (1887-1973). You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 155-156.

84. 15 Pettipaug Avenue, Rev. Francis Goodwin Cottage (1880)

    • Rev. Francis Goodwin (1839-1923) was one Hartford’s wealthiest and most important citizens. As Commissioner of Parks in the city he played the leading role in expanding Hartford’s Park system. For his father, James J. Goodwin, he designed c. 1893 a mansion on Woodland Street in Hartford. Familiarly known as the “Goodwin Castle,” the house was later torn down. Rev. Goodwin also designed c. 1880 a summer cottage for his family in the Borough of Fenwick in Old Saybrook. Rev. Goodwin led Sunday services in Fenwick in his own home until he designed and built a chapel on his property in 1883 that would be moved and enlarged in 1886 to become St. Mary’s-by-the-Sea. In 1910, Francis’ son Charles A. Bulkeley lost a bid for the governorship of Connecticut. The Goodwin family blamed the defeat on their Fenwick neighbor Morgan G. Bulkeley, who had used his influence against Goodwin. Because Bulkeley was a founder and leader of the Fenwick community, for the next thirty-five years the Goodwins rented out their cottage and vacationed elsewhere. Only after World War II did Charles Goodwin return to Fenwick. Located at 15 Pettipaug Avenue the Goodwin Cottage remained in the family until 1955, when it was purchased by Dr. Theodore Van Itallie and his wife Barbara Cox Van Itallie, who died at her Fenwick home in 2011 at the age of 91. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 115-120.

85. 21 Pettipaug Avenue, Dr. Joseph W. Alsop III Cottage (1880)

    • The summer cottage at 21 Pettipaug Avenue in the Borough of Fenwick in Old Saybrook was built c. 1880 for Dr. Joseph Wright Alsop III (1838-1891). The Alsops were a prominent family in Middletown: His grandfather, Captain Joseph Wright Alsop I (1772-1844), and his father, Joseph Wright Alsop II (1804-1878), were wealthy merchants; his son, Joseph Wright Alsop IV (1876-1953), married a niece of Theodore Roosevelt and was a politician and farmer in Avon; and his grandson, Joseph Wright Alsop V (1910-1989), was a journalist and top insider in Washington, DC politics. In later life Dr. Joseph W. Alsop III, a democrat, served in the state Senate and was involved in the political deadlock over the gubernatorial election of 1891. After giving an impassioned speech he collapsed at the rostrum and died of a heart attack. The cottage passed from the Alsop estate in 1903 and was acquired by Morgan B. Brainard of Hartford, whose former Fenwick cottage had been destroyed in the Hurricane of 1938. It was acquired in 1959 by his niece, Lucy Brainard Smith. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 122-128.

86. 25 Pettipaug Avenue, Knight-Whaples-Grant Cottage (1871)

    • The summer cottage at 25 Pettipaug Avenue in the Borough of Fenwick in Old Saybrook was built circa 1871 on land sold that year to Mrs. Cyrus Knight. Her husband, Rev. Cyrus Frederick Wright was rector of the Church of the Incarnation (later renamed St. James’ Episcopal Church) in Hartford from 1870 to 1877. He resigned after an incident in which church funds were stolen by the parish treasurer. Rev. Knight then served as rector of St. James Church in Lancaster, Pennsylvania, from 1877 to 1889, but continued to summer in Fenwick. When he became Bishop of Milwaukee in 1889, he and his wife could no longer make the long trip to Fenwick and therefore rented the cottage for the summer. Rev. Knight died in 1891 and his wife, Elizabeth P. Pickering Knight, in 1912. The cottage was then owned for a time by Heywood Whaples. It was purchased in 1952 by Ellsworth Grant (1917-2013) and his wife, Marion Hepburn Grant (1918-1986), the sister of Katharine Hepburn. The cottage has later rear additions. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 128-131.

87. 27 Pettipaug Avenue, Charles Eben Jackson Cottage (1881)

    • The Shingle-style summer cottage at 27 Pettipaug Avenue in the Borough of Fenwick in Old Saybrook was built in 1881 by Charles Eben Jackson (1849-1923) of Middletown. The cottage later sold to Margaret Cutter Goodrich, wife of Dr. Charles Goodrich, a Hartford obstetrician. The cottage then passed through other owners, being purchased by the Brainard family in 1949. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 131-134.

88. 26 Pettipaug Avenue, Walter C. Clark Cottage (1884)

    • Walter C. Clark, who became president of the Aetna Fire Insurance Company in 1892, built a summer cottage in Fenwick in 1884 on a lot he purchased from Francis Goodwin, who was on his board of directors. After Clark’s death in 1919, the cottage was acquired by Houghton Bulkeley (1896-1966), son of governor Morgan G. Bulkeley. Houghton Bulkeley, who named the cottage Seagrove, was an authority on Connecticut Antiques. After his death, the cottage was owned by the McDowell family. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 150-153.

89. 29 Pettipaug Avenue, Robert N. Jackson Cottage (1882)

    • The summer cottage at 29 Pettipaug Avenue in the Borough of Fenwick in Old Saybrook was built in 1882 by Robert N. Jackson of Middletown. The son of Ebenezer Jackson, Jr. (1796-1874) of Savannah, Georgia, and Middletown, Robert Nesmith Jackson (1845-1915) organized and served as president of the Middlesex Banking Company. The bank failed in 1913. In 1920 the cottage was acquired by Mitchell Little of Hartford and his wife, Elizabeth Hapgood, daughter of the architect Edward T. Hapgood. You can read more about the cottage in Marion Hepburn Grant’s The Fenwick Story (Connecticut Historical Society, 1974), pages 135-137.

90. Lynne Point Inner Lighthouse (1838)
    • A wood lighthouse on Old Saybrook’s Lynde Point was first lit in 1803. It was replaced by the current brownstone tower in 1838, which is similar to the earlier New London Harbor and Faulkners Island Lights, but is considered to be the finest of the three buildings. Lynde Point Light is an also referred to as the Saybrook Inner Light, in contrast to the Outer Light, or Saybrook Breakwater Light. A seawall was constructed to protect the original tower in 1829. The first keeper’s house stood from 1833 to 1858. This was followed by a Gothic Revival gambrel-roofed home, demolished in 1966 and replaced by a duplex, which houses Coast Guard employees. The Light was electrified in 1955 and automated in 1978
91. Saybrook Breakwater Outer Lighthouse (1886)

    • Saybrook Breakwater Lighthouse, a 49-foot cast-iron tower, first activated in 1886, is located at Fenwick Point, near Old Saybrook. Commonly known as the “Outer Light,” it assists the earlier Lynde Point Light, which is located a mile-and-a-half away, in marking the mouth of the Connecticut River. Saybrook Breakwater Light was built on a large sand bar at the harbor entrance and the interior was lined with brick to provide insulation. It was equipped with a 1,000-pound fog bell in 1889, but this was replaced with a smaller one after residents objected to the noise. The light was automated in 1959. An image of the lighthouse is also featured on the state’s popular “Preserve the Sound” license plate. In 2007, the Federal Government announced that the lighthouse would be sold under the provisions of the National Historic Lighthouse Preservation Act of 2000. The lighthouse is now privately owned.

92. 40 Ferry Road, John Whittlesey Jr. House (1693)
    • The main block of the John Wittlesey House Jr. house was built ca.1750, but its rear ell is much older. An estimated construction date is 1693. The house is in the Ferry District, a distinct settlement within the town of Old Saybrook. In 1662 the General Court of the Connecticut Colony authorized the establishment of a ferry across the Connecticut River at Tilley’s Point, which became Ferry Point. John Whittlesey and his brother-in-law William Dudley, were appointed to operate the ferry. The Ferry Distract prospered until the mid-1800s, declining with the introduction of steamboats, rail service and eventually the highway/trolley bridge across the river in 1911.
93. 1250 Boston Post Road, George Henry Chapman House
    • This was the home of George Henry Chapman, a direct descendant of Robert Chapman, the first Chapman in Saybrook. It was converted to commercial use and in the 1960s was the Yankee Homestead Furniture store. It is currently used for medical offices. This is a 5-bay central-chimney house with a central entry on the façade, capped with a semi-circular fanlight.
94. 108 Old Boston Post Road, John Pratt House (ca. 1720)
    • Built in 1720 by John Pratt, the house is also notable as the former home of Joe Cone and his family. Cone was an artist, writer, and printer. He proposed the creation of the Old Saybrook Musical and Dramatic Club—now the Kate. The shed out back was Cone’s print shop where he printed many of his literary works. The house today is a result of 300 years of “home improvement.” The post-and-beam construction of the original cape remains. The original floors remain in the den. The original chimney was entirely rebuilt at some point. Additions over the years include dormers and a bay window (1800s), extension of the brick fireplace (early 1900s) and the kitchen extension (2002). But the original 1720 cape remains the prominent profile of the John Pratt House.