Charm Alert Last Updated: November 2023
With its appealing historic architecture, village greens and tidy shops, Connecticut still does “charming” very well. In fact, there are immensely attractive little towns all across the state that—with their shops, restaurants, galleries and inns—are perfect for a visit and even an overnight stay.
Chester is a lovely little town on the west bank of the Connecticut River, surrounded by valley hills and with a center of town that’s right out of central casting. You’ll find yourself charmed by places like the rustic antique chestnut restaurant Brushmill by the Waterfall or new American River Tavern, galleries such as Lori Warner Studio and you will find a list of all the merchants here. And be sure to make a river crossing on the Chester/Hadlyme Ferry. Chester offers an array of lodging options, along with the Griswold Inn in nearby Essex, or The Copper Beech Inn in Ivoryton, are all great options to extend your visit to an overnight stay.
The Village, as it’s called locally, is unlike any other place in the state, in fact someone once wrote that it’s as if a piece of Nantucket had somehow separated itself and floated down to this southeast corner of Connecticut. Here, among its narrow lanes, the story of Stonington and the sea is everywhere, and it’s even home to the award-winning Stonington Vineyards and Connecticut’s last remaining fishing boat fleet. Try an overnight at The Inn at Stonington, a meal at Noah’s and a visit to the Old Lighthouse Museum and you’ll soon feel right at home.
This tiny town is situated on the shore of Lake Waramaug, arguably one of Connecticut’s loveliest lakes, where the colors blaze in the fall. There are shops in the tiny town, and a restaurant or two as well, such as The Hopkins Inn or the nearby White Horse Country Pub. And you should certainly drive, bike or hike the 8-mile loop around the lake and stop at Hopkins Vineyard along the way. Want to linger longer? The Windemere B&B offers guests a cozy, authentically New England experience.
An inviting village on Long Island Sound, Southport is also on the MetroNorth/Amtrak line, so it’s easily reached without a car. You’ll find shops and restaurants in the center, and it’s just a short hop to the beach. The 1889 Pequot Library is home to rare book collections and hosts fascinating events year round. Stay at the Delamar Southport, a boutique hotel that offers inviting rooms, gracious service, a spa and fine dining as well. Stop for a bite at The Gray Goose for a bit of local flavor.
Located on the Connecticut shoreline not far from New Haven, Guilford is a charming New England “beach” town that offers four seasons of attractions. Volunteers lead walking tours through the town pointing out the town’s 375 years of history, including The Whitfield House, the oldest stone house in Connecticut (1639) and a museum that offers a look at the lifestyle and culture of pre-colonial America. The Guilford Art Center offers classes, a shop and gallery showcasing handcrafted treasures. Stop by Ballou’s Restaurant and Wine Bar for a bite, and if you can enjoy a longer visit, stay right on the water at the Thimble Islands Bed & Breakfast, just down the road in Branford.
The town of Litchfield, at the heart of the Litchfield Hills region in northwestern Connecticut, draws visitors with a passion for New England's charm. Garden lovers from all over the country know the name White Flower Farm, and you can visit the home nursery here, even in the fall. You can also go for a hike at White Memorial, the state’s largest nature and wildlife sanctuary. Grab a table overlooking the town green at West Street Grill, or spend an afternoon sampling small-batch, premium spirits at Litchfield Distillery. If you’d like to stay the night and spend more time exploring, get a room at the historic and charming The Litchfield Inn.
Pomfret will give you a real taste of how charming northeast Connecticut can be. There is history at every turn of the road here, and much of it has been preserved in the houses and public buildings. There are long views and fall foliage treats in Pomfret, but you can also browse shops and galleries, stop for a bite at the Vanilla Bean Café, and enjoy the wine and the views at Sharpe Hill Vineyard. Not far from Pomfret, spend a night or two at The Inn at Woodstock Hill, one of the region’s most romantic inns. Or enjoy a cozy private cottage all to yourself at the Inn at Fox Hill Farm.
One of Connecticut’s most scenic towns, Ridgefield is tucked in the south western part of the state, not far from the New York border. Its elegant Main Street is filled with shops and restaurants, both old and new. The Aldrich Contemporary Art Museum on Main Street is a fixture of modern art, while just a few steps away, historic Keeler Tavern brings 300 years of Ridgefield history, including a famous Revolutionary War battle, to life. Stay in the historic West Lane Inn, and pick up dinner just next door from Bernard + Sarah's Wine Bar.