These are the 30 best small towns in Connecticut, according to Country Living

By: Andrew DaRosa • Published March 15, 2024

Connecticut’s quaint, seaside nature has earned the state the reputation of being a quintessential travel destination for exploring small towns. Connecticut has 169 towns, each with its own quirks and things to do.

Last month, Country Living magazine listed its 30 best small towns in the state of Connecticut. The list spans the entire state including towns in the “Quiet Corner,” the “Gold Coast,” Litchfield Hills and the Capitol Region.

“Connecticut is home to many wonderful things. Nestled on the New England stretch of the East Coast, it’s a state that has both beaches and foliage, adorable B&Bs, some of the most festive Christmas towns in the country and a vibrant art scene,” Country Living says about the Nutmeg State.

In total, five of the magazine’s picks are in Fairfield County, three in New Haven County, five in Middlesex County, four in New London County, six in Litchfield County, five in Hartford County and two in Windham County. Of the 30 “towns” named to County Living’s list, three of the locations are classified as villages by the state, not towns: Mystic, Collinsville and Niantic. Additionally, Milford and Middletown are classified as cities within Connecticut. 

Some notable activities in Connecticut’s small towns that Country Living highlighted were shopping down Greenwich Avenue in Greenwich, dining at the James Beard-nominated Shipwright’s Daughter in Mystic, fishing in Niantic Bay and taking a ride on the Essex Steam Train & Riverboat.

The recognition of Connecticut’s small towns by Country Living is the most recent in a string of acknowledgments. The towns of Ridgfield, Old Lyme, Chester and Kent were among the Connecticut towns recently named as the “best places to live in New England,” according to Yankee magazine. Last month, the town of Woodbury was named as the “most charming small town” in the state by Reader’s Digest. Woodbury also made Country Living’s list for the best small towns in the state.

In January, the town of Washington was recognized by travel magazine AFAR as the state’s most charming small town. The town of Washington was immortalized when it was revealed that it was the inspiration for Stars Hollow in “Gilmore Girls.” 

In a 2016 list from Country Living, Essex, Haddam, Mystic, Washington and Kent were among the best small New England towns to visit in Connecticut.