Perfect Connecticut Towns for Romantic Escapes

Reserve a room at the Inn at Longshore for sweeping views of Long Island Sound. Then head into town for a walk along the Saugatuck River and a stroll among the many boutiques and restaurants like OKO and The Whelk. Go star gazing at Rolnick Observatory or even kayaking at Sea Kayak Connecticut.

Not far from the scenic Connecticut River, Chester is a small town filled with art galleries, shops and fine dining. Nearby romantic bed and breakfast Boardman House will help to set a restful and relaxing mood. Head to Little House Brewing Company for a cozy drinking atmosphere or enjoy a relaxing ride on the Chester-Hadlyme Ferry for soaring views of Gillette Castle. Restaurants like Brushmill by the Waterfall and Grano Arso seal the deal with amazing food and warm, inviting ambience.

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. 

In the western Litchfield Hills, you’ll find the town of Kent, home to the famous Kent Falls State Park and cozy accommodation like the The Firefly Inn. 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!

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 premier oceanfront spots for a romantic sunset or sunrise stroll in the sand. Grab a bag of fresh oysters on the Connecticut Oyster Trail, 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 in its walkable towns.