Fairfield History

For thousands of years prior to English settlement, Fairfield, Connecticut was the home of Paugussett Algonquian Peoples. European settlers, led by Roger Ludlow, began moving into the area in the late 1630s following the Pequot War, and colonial Fairfield originally extended from the Saugatuck River in the West, to the Pequonnock River in the East, and inland through what is now Newtown, Connecticut. For more than a century, the community grew from the original “Four Squares” of land adjoining today’s Old Post and Beach Roads.

As the 18th century progressed, Fairfield became a home for wealthy New Englanders. Many influential families established their homesteads here, and with that wealth came a relatively large population of enslaved African and Native American laborers.

As tension between the American colonies and British Crown grew in the late 1700s, Fairfielders found themselves in the middle of the Revolutionary War. Many sided with the cause of American independence, including several notable patriots like General Gold-Selleck Silliman, American spy Caleb Brewster, and Samuel Smedley, a famed privateer. Others remained loyal to England and were often forced from their homes.

Fairfield, like other coastal Connecticut towns, became a target for the British Navy during the Revolution. On July 7, 1779, General William Tryon, along with revengeful American Loyalists and Hessian soldiers, laid waste to Fairfield, burning a majority of the town’s structures, and killing several townspeople.

Evidence of Fairfield’s 18th century past can still be seen as you stroll the Post Road historic district and Fairfield Museum Commons.  You’ll pass the Old Town Hall and Old Academy—one of Connecticut’s earliest schools, the Old Burying Ground, Sun Tavern, and the “witch dunking pond” where local women were accused of witchcraft 1692. Nearby, you’ll also see the First Congregational Church and the Burr Homestead, rebuilt after the Revolutionary War by Thaddeus Burr, a wealthy land owner and cousin to U.S. Vice President Aaron Burr. The house was the site of John Hancock and Dorothy Quincy’s wartime wedding in 1775.

In the years after the American Revolution, Fairfield’s economy struggled to recover.  But by the early 19th century, the town’s proximity to Bridgeport’s factories spurred an expansion in maritime trade, turning the quaint colonial town into a home for ship captains sailing out of Southport Harbor and Black Rock Harbor. In the 1840s, the railroad, steamships, and Bridgeport industry brought new opportunities to Fairfield while attracting newcomers from around the country and the globe. Black families leaving the South after the Civil War joined migrants from Hungary, Ireland, and other Eastern European countries in their quest to start a new life in Fairfield.