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11 Best Weekend Getaways in Connecticut

Although small, Connecticut is packed with exciting things to do and places to visit. The Long Island Sound ensures a scenic shoreline and sets the scene for many picturesque seaside villages and ports. Go to the center, and you’ll find the charm of New England with historic architecture, a traditional way of life, and plenty of outdoor activities. Cultural heavyweights like New Haven, Hartford, and Bridgeport bring the big city vibe into the mix. Proximity to New York City makes the Nutmeg State a perfect idea for a relaxed outing paired with wine tastings, superb dining, and accessible outdoor enjoyment. Here are the best weekend getaways in Connecticut for a rewarding and short New England vacation.

Chester Gillette Castle, Chester
Credit: Gillette Castle, Chester by © Rtdeleon04 | Dreamstime.com


Life is slower in lovely Chester, the gem of Connecticut River Valley. Pretty Victorian houses line the streets that drown in greenery, traffic lights are nowhere to be found, and outdoor activities are plenty. Hunt for antiques in the stores Downtown, have a coffee while observing the small-town movement from the terrace, and unplug surrounded by New England aesthetics. While here, it’s a sin not to check out the region’s most famous attraction and one of the must-see castles in the U.S., the phantasmagoric Gillette Castle standing next to the Connecticut River. It is, in fact, a mansion that belonged to the celebrated Sherlock Holmes actor William Gillette. Step inside to admire the elegant interiors, enjoy a hike at the state park nearby, and have a picnic with a river view.

Old Saybrook Old Saybrook
Credit: Old Saybrook by Rusty Watson via Unsplash.com

Old Saybrook

This Gold Coast town offers one of the most diverse propositions for a perfect weekend getaway in Connecticut. Geographically it’s simply stunning here. Old Saybrook stands at the confluence of the Connecticut River with the Long Island Sound. For a visitor, it means having access to the best of both worlds. See the iconic Lynda Point Lighthouse, marvel at sunset while strolling along Harvey’s Beach (one of the best beaches in the state), and tame the river on a kayak. End the day with a performance at the Katharine Hepburn Cultural Arts Center or a shopping spree at the Old Saybrook Shopping Center.

Essex Essex


One of Connecticut’s most charming towns, Essex embraces the riverside life. The Downtown here is a perfectly preserved New England city with wooden mansions, pretty old churches, and horse-driven carriages. Stop by the Connecticut River Museum devoted to the body of water nearby, have a drink at one of the many local bars, and book a ticket for the Ivoryton Playhouse, considered to be the first continuously operating summer theater in the country. But what really makes Essex stand out in Connecticut is the Steam Train and Riverboat. They have a variety of themed excursions with heritage locomotives and a historic boat that you should absolutely try. The dinner train with a 4-course meal is a go-to tour for a romantic outing. 

Mystic Mystic, Connecticut
Credit: Mystic, Connecticut by © Faina Gurevich | Dreamstime.com


You can’t talk about the best getaways in Connecticut and not mention Mystic. A gem of Connecticut’s seaside towns, it’s a combination of rich naval history, a quaint Downtown, and first-class island recreation along the shores of the Long Island Sound. The Mystic must-do is the Mystic Seaport Museum. The biggest maritime museum in the country, it boasts a large collection of ships, more than 60 buildings of a recreated historic village, and Charles W. Morgan, a.k.a. the last preserved wooden sailing whaler in the U.S. Visiting Mystic is a fascinating activity that will keep both adults and kids happy. For more underwater discovery, head to Mystic Aquarium with Steller sea lions and the only beluga whales in New England.

Westport Westport


Water is omnipresent in elegant Westport. A Gold Coast destination that was a star in Stepford Wives and American Housewife, it offers a perfect balance of upscale Downtown delights and excellent connection to nature. Visit the Westport Museum for History and Culture set in an 18th-century mansion, check out interactive exhibitions at MoCA Westport, shop on Main street, and explore the eclectic food offerings of the Downtown area. Then it’s time for active recreation. The Saugatuck River is a perfect spot for a kayaking adventure. On a clear day, head to the fantastic 235-acre Sherwood Island State Park for more fresh air and Manhattan views.

Litchfield Topsmead State Forest, Litchfield
Credit: Topsmead State Forest, Litchfield by © Tempestz | Dreamstime.com


Dive into history at Litchfield, one of the best weekend getaways in Connecticut if you’re after that Old World New England allure. Hidden deep in the northwestern part of the state, this small town is packed with authenticity, beauty, and some of the best fall foliage in Connecticut. Walking around Litchfield feels like stepping back in time. You’ll be surrounded by Georgian, Greek Revival, and Late Victorian architecture through its mansions, churches, and public buildings. Don’t miss the Litchfield Distillery that showcases the local whiskey and gin production, find peace at Topsmead State Forest, and tour the wineries around town.

Madison Madison


The glorious two-mile-long Hammonasset Beach (the largest in the state and one of the best on the East Coast) makes Madison one of the best weekend getaways in Connecticut if you’re into catching some fresh air. Picnic by the water, hike in the nature preserve nearby and give in to the unhurried atmosphere of the Gold Coast. The Long Island Sound is at its most magical here, the seafood restaurants are plenty, and the bustle of the bigger towns is far, far away. Don’t forget to check out Downtown Madison with colorful one- and two-story buildings housing cafes, bookstores, and restaurants.

Branford Branford


Located just an hour and a half drive from Manhattan, Branford is worlds apart. You may want to come here for its well-preserved historic center with delightful New England flair and a vibrant Downtown. But the real stars here are the magnificent Thimble Islands. Branford is the getaway to this unique Long Island Sound archipelago with more than 100 tiny islets. Board a cruise ship that snakes around the difficult-to-navigate Thimble Islands and enjoy the wild expanse of Connecticut maritime glory. Kayaking is also an option, and you can enjoy a seal-watching tour too.

Hartford Hartford


The high-rises of Downtown Hartford may give a false impression that you’re entering a big city. With a population of little more than 120,000, it’s just like Brooklyn’s Bushwick. Make it an ideal culture-filled weekend getaway in Connecticut by giving the superb local museums a chance. The Mark Twain House & Museum is one of the best things to do in Hartford. Occupying an American High Gothic mansion, it highlights the life and works of the titan of American literature. Proceed with checking out the Harriet Beecher Stowe Center located in the former house of the famous anti-slavery author. That’s not all for Hartford’s cultural agenda; you also have the exhibitions at Wadsworth Atheneum Museum of Art to admire and the family-friendly Connecticut Science Center to explore.

New Haven New Haven
Credit: New Haven by Zean Wu via Unsplash.com

New Haven

Catch a break at New Haven, which is home to the Ivy League Yale University. Modern Downtown buildings juxtapose the mannered Old World architecture of the Yale campus, the theatre scene is exceptional, New England charm abounds, and the art scene is flourishing. If this is your idea of a weekend getaway in Connecticut, New Haven is there for rewarding enjoyment. Start with Yale Center for British Art and Yale University Art Gallery to see the unparalleled collections of world-class works, catch a performance at the renowned Shubert Theater and 1926-built College Street Music Hall, and go on a culinary exploration of the rich food scene of the Downtown.

Salisbury Salisbury
Credit: Salisbury by Decaseconds via Flickr.com


Once you get to Connecticut’s northwest, the scenery starts changing. You’re in the land of endless green, frequent mist, and rolling hills. It may come as a surprise, but the Nutmeg State has its share of mountain fun too. You can walk part of the Appalachian Trail in Salisbury, the 2,316-foot-high Bear Mountain (the highest in the state) is located close to town, and there are many lakes and forests for hiking, too. For bird watching, fresh air-filled walks, and amazing natural panoramas, head to Mount Riga State Park. In other words, it’s quite an outdoor lover’s paradise in Salisbury.

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