Start your walking tour at the corner of the Post Road West and Wright Street.

Wright Street was established between 1835 and 1838 by Charles Wright who built most of the Greek revival houses between 1845 and 1856.

15 Wright Street - Home of Judson P Wright, son of Charles and Polly Wright.  The front exterior has not changed since it was built in 1851.  Two front Windows have old panes.  Rear wing added later.

21 Wright Street - Home of Polly Wright after the death of Charles.  Built about 1848.  Remained in the Wright family until 1918.  Contains some old windowpanes.  The front exterior remains largely unchanged. 

25 Wright Street - Home of Charles and Polly Wright, built about 1845.  The rear wing was added later.  The front remains exterior largely unchanged.

35 Wright Street - Built about 1852 for Zalmon Sanford, a founder of Westport Bank & Trust.  Sold in 1854 to Peter Bennett, river captain and then to Peter Buckley, also a river captain, in 1867.  The front entrance and garage were added in 1960 and have been remodeled in 2024 with features more consistent with the time period of the house.

41 Wright Street - Also built about 1852 for Zalmon Sanford.  Sold to Peter Buckley in 1857.  Remained in the Buckley family until 1927.  House has been remodeled.  

46 Wright Street - Probably constructed about 1840.  A mansard roof was added in 1868.  Through the 1800’s residence of Edmund W. Taylor, President of the old Westport Savings Bank. 

49 Wright Street - Built in 1854 for the Jackson family.  Greek revival portico and columns added in 1960’s.

54 Wright Street - Built c. 1840 for Jesse Bradley.  Remodeled by Erick Jackson in 1877 in Italianate flat-roofed style, with brackets and cupola.

63 Wright Street - Clapboard house with wrap-around veranda in late Victorian style, built 1889.

64 Wright Street - Simple Greek revival house-built c. 1840.  Rear addition built in 1910.

67 Wright Street - Behind #63, two-story clapboard built for Charles Foote in 1856.  Veranda added later.  Was in the Nash family 1866-1935.

74 Wright Street - Built 1853 for Aaron Bennett, remaining in his name until 1901.  Extensively remodeled in 1966.

80 Wright Street - Built in 1854 for Allen Renaud, remaining in his name until 1900.  Later remodeled.

Kings Highway North was part of the first postal route started between New York City and Boston in 1672

67 Kings Highway North - Simple clapboard farmhouse built in the late 1700’s by Samuel Lord.  Owned in 1864 by Capt. Joseph Nash. Front porch added later.

57 Kings Highway North - Oldest portion of the house was grist mill, believed to have been built c. 1730 and moved here by Daniel Nash in the early 1800’s.  This section of the house was built around a huge chimney with extra-large ovens for baking bread.  The front portion of the house was built in Federal style by Dennis Nash c. 1812.  Behind the house are remnants of an old apple orchard planted before 1812.  John Chapman, writer and drama critic for the N.Y. Daily News lived here from 1936 to his death in 1972. One summer it was rented to actor David Wayne.

52 Kings Highway North - Two-story clapboard, bought by Zalman Sanford, first partner of Horace Staples, in 1838.  From 1920 to 1941 this was the home of author Van Wyck Brooks, and it was in this house that he wrote “The Flowering of New England.”

49 Kings Highway North - Constructed in the late 1700’s by Dennis Nash, it remained in the Nash family for over 200 years.  Has two living rooms with original fireplaces and baking ovens.  Seaweed was used as insulation.

45 Kings Highway North - Built about 1780 as a two-family residence.  Originally had center chimney, now blocked off.  Also on the grounds are an old barn and smokehouse.

41 Kings Highway North - Built 1727-1730.  Until 1810 the successive owners, who also operated the nearby grist mill, were Noah Taylor, Nathan and Sarah Bears, and David and Freelove Nash.  The house was not originally a saltbox.  The gable overhang indicates that it was at first only one room deep and the lean-to was added later.  It contains five fireplaces, a beehive oven and a central chimney 10 feet square.  The house has flared posts and the beams run diagonally in every room.  It has vertical board wainscoting edged by a simple beading.  The original paneling and windows remain.  The eight-paneled front door flanked by a pair of very narrow three-light windows was a later substitution for what was probably a plainly framed, transom-lighted door.

40 Kings Highway North - Original portion of house having an immense stone chimney, was built in 1733 by Dennis Wright, great grandfather of Judson Wright, later residing at 15 Wright Street.  The front section was a small farmhouse moved from a nearby site and added on in 1911.  Original chestnut and oak beams remain.  House was owned around 1890 by Horace Staples, who built first high school in Westport, and was President of the First National Bank, now the Westport Bank & Trust Co.

38 Kings Highway North - Formerly Town’s West Saugatuck District School, known as “Shercrow School,” moved from town-owned land at front edge of lot.  Built c. 1812.  Extensively remolded.

76 Kings Highway North - Lot sold by Susannah Wright to Anson Gorham in 1855.  Basic house is simple Greek revival.  Bought in 1907 by William S. Hart, famous movie actor, in 1907 for his mother and sister.  Porches, house extension, garage and landscaping all added by Hart.

75, 79, 83 Kings Highway North - All built in the 1920’s in colonial revival style.  75 and 79 designed by Charles Cutler who was architect for several other houses in the area.

78 Kings Highway North - Built by Dennis Wright c. 1760, deeded to his son Obediah in 1767.  Remained in the Wright Family for over 100 years.  The wing was added in 1915 when owned by Mrs. Lillian Wadsworth, donor of Nature Center property.  At the rear of the property is a one-room building with balcony, which is supposed to have been a cobbler’s shop-built c. 1690.

1 Old Hill Road – This saltbox built in c.1690 by Lt. John Taylor.  This was considered a one-story house with a loft which avoided Queen Anne’s tax on two story houses.  The children slept in the loft.  It was destroyed by a fire in 1935, and this house is a replica built on the original foundation. Its first owner was Lt. John Taylor, progenitor of the Westport Taylors, who lies in the “old King Street Cemetery”, corner of Wilton Road.  Well known actor Arthur Kennedy lived here from 1952-1960.

B - The triangle of land between Old Hill and King’s Highway North is what remains of an old drill ground used for training by the local militia after the French and Indian War.  Last used during the Mexican War.

A - Christ and Holy Trinity Cemetery (1852). Contiguous is Assumption Church Cemetery (1900).

96 Old Hill Road - First records show purchase in 1792 by Moses Bennet from David Juday.  Bought by Isaac Adams in 1822 and remained in his family until 1843.  Many additions to the original four-room section.

104 Old Hill Road - Originally a four-room farmhouse built by Samuel Burwell c. 1769.  Contains central fireplace and Dutch oven.

6 Edge Hill Lane - “Edgehill House.”  Built by Taylor Hurlbutt in 1797.  Wings and gables added 1878 by Rev. James Coley who used part of his home as a school.  Coley is the author of “Historical Notes and Reminiscences of Old Saugatuck, Westport and Vicinity with Notices of Old Houses and Old Families”.  Remained in the Coley family until 1945.

109 Wilton Road - Front section built in the early 1800’s; rear part appears to be much older.  Owned by Isaac Hurlbutt 1782-1831.  House has undergone extensive renovations in 2024 retaining its original characteristics.

107 Wilton Road - Built by Hurlbutt family c. 1750.

C - The Old King Street Cemetery (1721) Corner of King’s Highway North and Wilton Road - The names of every early family owning dwellings in the Historic District are represented here, including Bulkley, Hurlbutt, Marvin, Nash, Taylor, Wright.  The earliest burial was January 29, 1721.  Contains the graves of 17 Revolutionary soldiers.  In 1777 the Norwalk Militia under the command of Col. Ozia Marvin, who is buried here, set up a cannon at the cemetery in an attempt to route British Troops as they crossed the bridge returning to their ships at Compo Beach after the raid on Danbury.  In 1884 the Rev. Coley recorded inscriptions of many of the stones which were deteriorating and now cannot be deciphered.  In 2024 a marker honoring Civil War Brigadier General Henry Moses Judah was installed in front of the tomb where he was interred, along with his parents and several others in this communal grave.