Rediscover Kent

The allure of the southern Berkshires is well-known with culturally rich communities attracting both second-home owners and day trippers. All these towns have their individual character but a shining star among this constellation is Kent, one of the region’s southern-most towns.

A “destination” town, the community has received many accolades, from its 2010 Yankee magazine designation as “Best Fall Foliage Town” to its most recent recognition in July by Reader’s Digest as having one of the “20 Most Beautiful Main Streets in America.”

“Main streets have character,” observed the Reader’s Digest. “At one time, you could walk down the main street in your town and stop at the grocery store, the hardware store and the library all on the same block. Those days might be over for many of us … but some main streets never lost that old-fashioned feel. … Lined with historic buildings, cozy cafés and local boutiques, these streets invite you to slow down and soak in their one-of-a-kind character.”

Kent neatly fits into this description. It has a charming, small-town appeal including locally owned stores and town events and festivals. Twinkly lights wrap around charming inns and shops on Kent’s beautiful main streets, lending a cozy New England vibe.

It matters not when you visit the community—summer festivals easily morph into fall events, only to be followed by winter holiday celebrations. Even the darkest winter nights cannot quench the community’s spirit as it lights up in February to celebrate poet Robbie Burns with an evening of Celtic revelry complete with bagpipes and a ceremonial “Address to a Haggis.”

While the summer crowds are dwindling slightly, several weeks of warm-weather pleasures still remain—and, of course, there is that impressive fall foliage display.

Kent’s business community is an amalgam of attractive shops, art galleries and restaurants. It’s no secret that Kent is a hidden gem when it comes to fine dining and shopping. Restaurants range from tavern favorites to fine dining to Mexican cuisine with many eateries working closely with area farms to source local meats, produce and dairy.

A panel of food experts recently took notice and acknowledged two Kent restaurants, Ore Hill and Fife ‘n Drum Restaurant as standout favorites in Connecticut Magazine’s top restaurants for 2025. Since then, a new addition, The Kent Kitchen is receiving rave reviews for its sushi and other offerings.

For those who want to take a taste of Kent home with them, the Kent CT Farmers Market is held every Friday (rain or shine) through mid-October from 3 to 6PM on the Kent Land Trust field, just south of the village center on Route 7. With a variety of vendors selling farm produce, beer, meals-to-go, baked goods, local honey, homemade crafts and jewelry, there is always something to love.

But shopping and eating are not the sum total of the tree-lined community. It also has a rich history as a center for art, that started in the first decades of the 20th century when an art colony formed there. The Kent Art Association (KA) was founded in 1923 by nine well-established artists who knew each other when they lived in New York before moving to Kent.

Among them were Rex Brasher, whose ornithological rendering have been compared to Audubon’s, Eliot Clark, a well-connected practitioner of Impressionism; Floyd Clymer, known for his Regionalist style of land, sea and cityscapes; William Dryden Paddock, an American painter and sculptor, F. Luis Mora, a renowned figural painter; Spencer Nichols, a portrait painter and muralist probably best known as a designer for Tiffany Studios; Robert Nisbet, noted for his landscape, figure, genre, and etching work; Frederick Waugh, a marine artist, and George Laurence Nelson, a society portraitist.

The foundation they formed continues today in the Kent Art Association gallery, one of seven venues in Kent that host revolving exhibitions year. Morrison Gallery described as "the linchpin of Litchfield County’s art scene" by the New York Times Recently reopened in a newly built 6,500-square-foot gallery with 24-foot-tall ceilings, it exhibits monumental works inside and out, representing national and international artists.

The former home of KAA founder George Laurence Nelson, Seven Hearths, has now become headquarters for the Kent Historical Society one of three museums in the community. Nelson and his wife Helen, moved to the mid-18th century building in 1919 and he lived and worked there until his death in 1978. He bequeathed the building, one of the earliest still extant in the town, to the historical society which has painstakingly restored it to reflect its different uses over the centuries. It contains a large collection of Nelson’s works.

Just down the road, the Eric Sloane Museum celebrates another local artist. Sloane, a renowned artist and author of 38 books on Americana, donated his paintings, illustrations and an extensive collection of early American hand tools to the museum as a tribute to American artisanship.

Outside visitors can view Noah Blake Cabin, a recreation of an early 19th-century dwelling from Sloane’s most famous book, Diary of an Early American Boy. Explore the museum’s scenic grounds near the Housatonic River including the ruins of the Kent Iron Furnace and enjoy picturesque walking trails.

Adjacent to the Sloane Museum is the Connecticut Antique Machinery Association’s sprawling campus with multiple buildings featuring steam-powered machinery, tractors and rock collections. Included in its exhibitions are the Cream Hill Agricultural School, reputed to be the earliest agricultural school in the nation, and a mining museum exploring the history of Connecticut's varied geology.

Many people come to the country to enjoy just that—the country. Kent provides many sylvan opportunities in its three state parks and there are also trails open for hiking at the Town’s Emery Park and on Kent Land Trust.

At Kent Falls State Park visitors can take photos of “Connecticut’s Highest Waterfall” while enjoying its spacious picnic area. Or perhaps they would wish to explore the many trails in the 2,300-acre Macedonia State Park or take a swim at Waramaug State Park. When vivid fall foliage is mirrored in the unrippled lake surface, the park becomes a mecca for sightseers and photographers.

If you really like walking, gear up for a hike along the Appalachian Trail.

Clearly, there is more to do in Kent than can be accomplished in one day. Happily, the town is poised to welcome guests for longer visits at any one of its inns or beds & breakfast.

For further information, go to www.kentct.com.