Perfect Connecticut Towns for Romantic Escapes Last Updated 9/19

When it’s just the two of you, nothing is better than a small town with romantic charm. From coastal Connecticut to the state’s northeastern “Quiet Corner,” the state is home to stylish towns and quaint villages that are perfect for sparking, or recharging, romance. Here are just a few of our favorites, and some things you can do to make the visit even more romantic.

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Westport Wanderings

Reserve a room at the Inn at Longshore for sweeping views of Long Island Sound or check into The Westport Inn for boutique style comfort. Head into town for a walk along the Saugatuck River and a stroll among the many boutiques and top-rated restaurants like Tavern on Main and The Whelk. Check what’s on for music under the stars at the Levitt Pavilion, or do even more intense star gazing at Rolnick Observatory.

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Chester Charm

Not far from the scenic Connecticut River, Chester is a small town filled with art galleries, shops and fine dining. Nearby romantic bed and breakfasts, like Riverwind Inn and Boardman House help to set a restful and relaxing mood. Take in a never-before-seen performance at the Norma Terris Theatre or a relaxing ride on the Chester-Hadlyme Ferry for soaring views of Gillette Castle. Restaurants like Brushmill by the Waterfall and The Good Elephant seal the deal with amazing food and warm, inviting ambience.

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Woodstock Wonders

Book a room at the Inn at Woodstock Hill and make it your home base for exploring this quiet-corner gem of a town. The one-of-a-kind Roseland Cottage Museum offers a walk back in time and a stroll through lovely gardens. Make sure you visit Soleil & Suns Bakery for some artisan bread and desserts and bring them along to a tasting at Taylor Brooke Winery, one of the state’s most scenic vineyards. 

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Fall for Kent

In the western Litchfield Hills, you’ll find the town of Kent, home to famous waterfall hikes and cozy accommodations like the Kent Victorian and Cooper Creek B&B. Browse for treasures at Main Street Antiques, stop for a beer tasting at Kent Falls Brewing Company or enjoy a meal with the locals at the Fife & Drum. If you’re visiting in the summer, don’t miss Connecticut’s grown up summer camp experience at Club Getaway in Kent!

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Madison Magic

Tuck yourself into a room at the Scranton Seahorse Inn or the Madison Beach Hotel and then set off to experience everything there is to love about this laid back beach town. Start at the famous R.J. Julia bookstore and have a snack at the RJ Café & Bistro. In the summer, or even in off seasons, Hammonasset Beach State Park is one of Connecticut’s premiere ocean front spots for a romantic sunset or sunrise stroll in the sand. Get your seafood fix at Lenny & Joe’s Fish Tale or Clam Castle, or savor authentic French fare at Bar Bouchée

Whether you’re looking for quaint or contemporary, Connecticut dials up the romance all year-round in these and more great towns.