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Connecticut's Charming Towns - Fall Destination Favorites

Connecticut’s small-town rhythm inspires new experiences. Strolling through unique boutiques create a poetic ambiance, where delightful wares and sourced-local fare offer a real breath of fresh air.

Kent, selected as the top foliage town in New England by Yankee Magazine last year, invites you to enjoy the colorful energy of a charming Northeastern town. Bookstores, antiques shops and boutiques tuck away in pockets around the main street. The Morrison Gallery features noted artists in an expansive space.

Nestled in the scenic Northwest Hills, historic Litchfield is anchored by the most photographed church in the state. Across the green, Litchfield Historical Society Museum preserves art and artifacts from the 18th to the 21st centuries. Cruise down the main street to find shops, cafes and art galleries.

In the historic community of Guilford lies a green at the heart of this classic Colonial village. Stroll the perimeter for fine restaurants and cafes, one-of-a-kind shops, galleries and historic museums with 17th century artifacts.

The 1634 village of Wethersfield claims to be the state’s “most ancient town.” Civic pride is obvious at every turn, where the preserved homes of historic figures now document the relics of battles and trades long past. A period piece in every way.

Home to the state’s longest public beach, the town of Madison, located on Long Island Sound, retains its small-town atmosphere with local shops and friendly café culture. Curl up on the shore with a book from R.J. Julia Booksellers, and embark on a sculpture hunt through downtown.

The enchanted town of Chester celebrates life in the form of art, history, music, theater, crafts, cuisine, community and conversation. Located in the magnificent Connecticut River Valley, it boasts nearly 40 galleries.

Main street acquires a whole new meaning in “the best small town in America,” Essex. Wander up and down Main Street and experience elegant dining and high-end boutiques and galleries. At the end of Main Street, on river’s edge, visit the Connecticut River Museum and discover the state’s great maritime history through detailed models of vessels and nautical artifacts.

The historic waterfront district of New London gives visitors a first-hand look at life in Colonial times. Take a self-guided tour to find the 30 bronze plaques along the Heritage Trail. Visitors also hunt for heritage in Putnam, known far and wide for its antiques district. Uncover ties of the past in the form of collectibles that tell the story of the region.

Fall in love with “the most beautiful seaside village in New England,” otherwise know as Stonington Borough. Here, the air is refreshed by sea breezes, the tree-lined sidewalks lead to quiet waterfront viewing and the lighthouse museum ignites a whole new perspective. The village houses sophisticated bistros, friendly coffee shops, and many boutiques and galleries.

The historic town of Westport thrives in its culturally rich past as well. Discover pockets of shops and meet people filled with anecdotes and pride. The interactive explorer will appreciate Greenwich, with its plethora of cultural events and high end shops. And traverse the dynamic town of New Canaan where the discoveries pop up one after another.