Incorporated in 1835. Colonized in the 1630s. Inhabited for centuries. Westport has a long past, yet many know little about the history that’s all around them. Join the Westport Museum on a journey to tour the most well-known locations, and some mysterious spots, in our beloved town. 

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Take It On the Road!

If you’d like to take a pdf onto the road download our driving tour packet here!

1. Marvin Tavern 

Captain Ozias Marvin and wife Sara, the great aunt of LeGrand Lockwood of Lockwood Mansion in Norwalk, owned the Marvin Tavern along the Kings Highway in the 18th century. During the 1777 Danbury Raid the inn and tavern supplied Continental troops. Marvin’s Inn also hosted George Washington when he passed through Westport on his way back from Boston in 1789. Local legend has it the Marvin’s presented the General with an extravagant meal but he refused and requested a simple dinner.

2. Kings Highway & Green 

The Kings Highway was ordered by King Charles II to connect the colonial cities of Charleston, South Carolina and Boston, Massachusetts in the mid-17th century. Prior to and during the War for Independence colonial militia men used the triangular green at the corner of Kings Highway and Old Hill as drill grounds. Town greens were also the site for market days and other public gatherings.

3. Old Hill Cemetery 

Predating Greens Farms Colonial Cemetery by 3 to 4 years, Old Hill boasts the oldest known grave in Westport. The Taylor family dominated the neighborhood known as King’s Highway in the late 17th and early 18th centuries, giving the area the nickname “Taylortown.” Old Hill not only served as this prominent family’s cemetery but also as a staging ground for cannon during the 1777 Danbury Raid. Benedict Arnold and his troops lay in wait at the High Ground of Old Hill for British troops returning from the assault on Danbury. Hearing that the patriot General was on site, the British changed course to arrive at their waiting ships safely. Members of Westport’s first Jewish family, the Judahs, also reside in one of the five vaults within the burial ground.

4. Willowbrook Cemetery 

Willowbrook Cemetery was created as a non-denominational resting place for Westport residents in the mid 19th century. It didn’t become fashionable until the 1870s when prominent landscape designer Frederick Law Olmstead took the helm of a project to expand the graveyard. Olmstead had famously designed New York’s Central Park, San Francisco’s Golden Gate Park and, more locally, Beardsley Park in Bridgeport. Some of Westport’s–and the nation’s–most notable residents rest here. 

5. Veterans Green 

J. Clinton Shepherd, created the bronze WWI doughboy statue to honor Westport’s veterans of that conflict. Costing more than $10,000, the funds for the statue were raised by a group associated with the American Legion. The formal dedication occurred on November 11th, 1930 at its original location in a median near Long Lots Road. Due to the expansion of the road and increased traffic the monument was moved in 1986 and rededicated on Memorial Day in 1988. 

6. Bradley Wheeler House 

Ebenezer Coley, a noted farmer and landowner, built the original five bay colonial house on this site in 1795 for his son Michael, while his own home was on North Avenue. The structure not only served as a living space for Michael and his enslaved people, but also as a place of business. The house would be used as a millinery shop, dentists office and surgeon’s office through history. By 1865 the Wheeler family purchased the home and renovated the house into its current style. 

7. Coley’s Saugatuck Store

Ebenezer Coley was a prominent farmer and merchant whose downtown store was managed by his son Michael. Michael lived in the original house at what is today 25 Avery Place, site of the Westport Museum, along with several enslaved people who helped him manage the store. The store sold goods such as grain grown at the Coley farm in what is today Coleytown. Loaded onto ships from a dock off the back of the store the grain and other goods traveled to the West Indies via New York City to feed enslaved people and support sugar plantations. 

8. Parker Harding 

The Saugatuck river served as a water highway prior to the rise of train and automotive shipping beginning in the mid-19th century. The area known today as the Parker Harding lot was entirely water; docks extended from stores along Main street, into the wide, deep river which was dredged until the 1950s.  

9. Downtown Bridge 

Since 1807 a bridge has been used to cross the Saugatuck, prior to that people forded the river at the location of the current Kings Highway Bridge at low tide and at high tide, about two miles up-river by Ford Road. The bridge currently in place downtown is named in honor of noted activist, Ruth Steinkraus Cohen, who originally organized the now-popular UN Day in Westport. 

10. YMCA & Anthropologie 

E. T. Bedford had not been a fan of the billiards room and bar next to the old Westport Hotel after being barred from admission as a young boy. After he made his fortune and returned to Westport, he decided to tear down the old establishment and erect a new place for the young people of Westport to congregate and enjoy themselves without liquor to which Bedford was staunchly opposed. The Y.M.C.A. was dedicated in an all-day ceremony on September 5, 1923. The building was a central focus of downtown life until 2015 when the Y.M.C.A. moved to a new location with state-of-the-art facilities. This classic building was refurbished and now houses retail establishments. 

11. Toquet Hall 

Toquet Hall is, today, a teen center but was built by Benjamin Louis Toquet as an Opera House in 1892. Toquet made his fortune as an engineer and inventor, making small pleasure yachts, boat engines, and carburetors for boats and automobiles (most notably for the Ford Motor Company) through his own Toquet Motor Company. 

12. Old Town Hall

Listed in the National Register of Historic Places, the Old Town Hall is unique in its use of cobblestones as a building material. Prior to its building in 1908, Town business was conducted at various locations including the Saugatuck Congregational Church the first floor of Toquet Hall just a few doors down the street. In 1979, Westport Town Hall was relocated to the old Bedford Elementary School opposite Veterans Green on Myrtle Avenue. Today, Old Town Hall houses offices, restaurants, and retail establishments. 

13. Minute Man Statue

Created by H. Daniel Webster and cast out of bronze by Tiffany Studios at Roman Bronze Works in New York City, the Minute Man statue stands in defense of Westport’s shoreline. In 1777 when British forces landed at Compo Beach to raid Danbury, colonial militia mostly comprising local farmers defended the shore as the British retreat neared their ships. The statue was dedicated in 1910 by the Sons of the American Revolution.

14. Grave of Henry Gray

The marker placed at hole 13 at the Longshore Club Park contains the original headstone from 1731 of Mr. Henry Gray. Gray lived in what is today Westport, but during his time the town was still incorporated as part of Fairfield. In 1648 Gray’s father, also named Henry, along with Thomas Newton and John Green, settled along the Long Island Sound after being given a land grant with the “liberty to set down” in the area. Shortly after these bankside farmers came other families, including those of Daniel Frost, Francis Andrews and Joshua Jennings.  

15. Machamux Park 

Prior to 1630 the land known today as Westport was used by the Paugusset People’s as seasonal living and hunting sites. After European colonizers landed, local tribes including the Pequots, waged war to continue their way of life but were largely erased from history after their defeat at the Great Swamp Fight in 1637 and the subsequent enslavement of those not killed. Later, Greens Farms first school (1703) and meeting house (1711) stood on the common at Green’s Farms Road and Morningside Drive, commemorated today by the Machamux boulder.  

16. Compo Beach 

April 25th marked the landing of British soldiers making their way to seize the colonists supply depot of food, tents and other dry goods in Danbury. Over the next three days the British were harassed and ultimately repulsed from the Connecticut colony’s coastline. As the British regulars retreated, cannon fire from their waiting ships aimed at the militia encamped on higher ground. In 1901 the US Government donated two cannons to mark the spot of the retreating British. Sealed, and later replaced, the cannons continue to remind visitors of the period involvement in the War for Independence. The beach served not only as a memorial to past conflicts, but also as a plane lookout during World War II.

17. Sherwood Island

Frederick, Franklin, and Francis Sherwood were identical triplets who hailed from a 17th century Westport Family. Their father Daniel built his home on what is, today, known as Sherwood Island. When they were not seeking adventures on the high seas in places as far away as Mexico, Africa, Brazil, China and the Caribbean, the Sherwood triplets, like their ancestors, lived in Westport for the duration of their lives. The first plot of land was purchased in 1914 by the state, and the park has remained a public beach and recreation area since it opened in 1937.

18. Greens Farms Colonial Cemetery

Owned and overseen by the Greens Farms Congregational Church, the colonial Cemtery is among the oldest in Westport. Not only do founding families reside here but also soldiers from the Revolutionary War, and other conflicts such as the French and Indian war, Civil War and World War I. Westport’s documented Black residents rest in the graveyard as well in an unmarked burial area where enslaved people were likely laid to rest; Two individual plots with their marble headstones lay fallen on the ground commemorating two members of the Monroe family the longest-residing free black family in Westport. 

19. Greens Farms 2nd Meeting House

Today the open plot at the corner of Greens Farms Road and the Sherwood Island Connector belongs to the State of Connecticut, but in the 18th century it hosted Greens Farms second meeting house, the West Parish Meeting House. Part church, part town government building, the meeting house hosted services for the then-section of Fairfield as well as town debates over governance. In 1779 the British burned much of Southern Connecticut’s coast from Fairfield down to Norwalk. The meeting house and several homes were all torched, but not before the church’s communion silver tankard was saved by placing it down a well. 

20. Adams Academy 

Ebenezer Adams preparatory school, named Greens Farms Academy, began its first-year session with only six students registered; by the end of that year, 1837, enrollment had risen to 28. Not related to the current Greens Farms Academy, the school, which taught pupils beyond the customary 8th grade equivalent, prepared students for college enrollment, of which all students that applied from the small academy were accepted. Adams taught until 1867 and the building has been used by the town for a variety of purposes, including offices and a third-grade classroom. Today the school house is owned by the town but used by the museum for educational purposes.

21. Winslow Park 

Prior to becoming the Westport Sanitarium, the property at the corner of Post and Compo Road had been the lavish home of State Senator Richard Henry Winslow. The “Winslow Mansion” was built in 1853 and the annual firework display on the property brought President Millard Fillmore to Westport in 1859. In 1891, the property was transferred to Dr. Fredrick D. Ruland for treatment of the mentally ill. Many years later, after the sanitarium’s closure, the mansion, then called Compo House, and the associated hospital buildings fell into serous disrepair.  

22. Westport Country Playhouse 

Opened during the Great Depression, The Playhouse featured a Broadway quality stage and was quickly considered an important stop on the New York summer stock circuit.  Broadway and film could hone their skills with workshop productions. Notable actors including Paul Robeson, Helen Hayes and Ethel Barrymore have graced the Playhouse stage over its nine decades.  

23. Saugatuck Congregational Church 

Saugatuck Congregational Church was created by citizens who tired of the few mile carriage ride from what is today downtown Westport to Greens Farms Congregational Church. In 1835, church congregants Daniel Nash and others signed a petition to the State Legislature to create an independent town to be called “Westport”. For a time, town meetings were also held at the Church. In 1950, the church was physically moved across the Post Road to its current location in a feat of engineering that made the cover of Life magazine. 

24. Disbrow Tavern and Christ & Holy Trinity Church 

Accompanied by his enslaved servant William Lee, who was by his side throughout the Revolutionary War, on June 28th, 1775 George Washington stopped at Disbrow’s Tavern on what was then the King’s Highway or Main Road of the town. Newly commissioned by the Continental Congress as Commander of the Continental army Washington was on his way to Lexington & Concord to take command of the troops there. Washington may have possibly met with members of his espionage circle at the tavern at a later date. 

Originally called Holy Trinity Church, in 1944 the congregation merged with Westport’s original episcopal church, Christ Church, built in 1832 to become Christ & Holy Trinity. Many notable members of Westport high Society attended the church. In 1955, famed actor/dance Geoffrey Holder and Carmen De Lavallade married here.