7 Charming Connecticut Towns For The Perfect Getaway

With its picturesque coastal towns, small and charming villages, and quiet forest trails, Connecticut has several options ideal for the perfect getaway. Whether looking for sea breezes and nautical charm, beautiful architecture, or outdoor attractions, you will not miss finding a town with your name on it. Keep in mind that in many of these places, you can amble through a beautiful downtown area, lounge on a white-sand beach, and wander through a sun-dappled forest — all in a single day. From adorable Mystic to Old Saybrook, discover below 7 charming Connecticut towns for the perfect getaway.

Mystic

Mystic is a historic shipbuilding village known for its rich maritime history, nautical charm, and a lovely downtown area beautifully positioned along the banks of the Mystic River. The river adds a tint of rustic allure to an already spellbinding space. You will enjoy walking along its edge and sipping in the heartwarming scenery on every side. Step aboard the Schooner ARGIA, a traditional sailing ship that does four daily trips, and lose yourself in a world of breathtaking natural beauty that intertwines with bits of interesting history and culture. If you have a thing for whales, the Charles W. Morgan is the last of an American whaling fleet that once numbered nearly 3,000 vessels. That said, a good way to start your trip is to pass by Sift Bakery, a French-inspired establishment whose owner was in 2018 named the Best Baker in America.

Stonington

This may be a little confusing, but Mystic is part of Stonington, a nice, breezy town whose boundary begins on the eastern flanks of the Mystic River. Stonington has a scenic waterfront, historic architecture, and a nice, laid-back atmosphere. You will enjoy strolling along the tree-lined Water Street and admiring the nice, historic homes, most of which are framed by white picket fences. A few steps and you will find the aptly named Stonington Free Library, a small, quaint space with eye-catching architecture. If you are craving a filling bite, Noah’s is a charming little place to sit and enjoy freshly made food, whether scallops, oysters, or some melt-in-the-mouth blueberry pancakes. Check out the picturesque harbor as well as the iconic Stonington Harbor Light and Lighthouse Museum — the first one established by the United States federal government in the 19th century.

Madison

James Madison, like Sir Isaac Newton, Beethoven, and George Washington, did not have a biological child of his own. However, his name and legacy linger in the many towns named for him, including Madison, Connecticut, a soothing, shoreline town midway between New York City and Boston. Stroll the boardwalk, and enjoy the restful rhythm that pervades almost every open space. Alternatively, pick a gripping read at R.J. Julia Booksellers, one of the best indie bookstores in America. This unassuming bookstore has won multiple awards in the state, making it a bibliophile’s dream destination. Plus, it has a cafe in the back that makes nice lattes in a warm, welcoming environment. That said, no one voluntarily misses Hammonasset Beach State Park — the largest sandy expanse in the state. You will find grills, picnic tables, and pavilions for shade. Meigs Point Nature Center, with its gorgeous gardens, is a stone’s throw from here.

Chester

Chester has a downtown that is small but incredibly nice and artistic. Boasting a setting on the hillside of the Connecticut River, Chester still does not get the attention it so richly deserves. You will discover a picturesque Main Street with interesting architecture, mind-rousing art galleries (such as Leif Nilsson Spring Street Studio and Gallery), and boatloads of inviting restaurants. Speaking of restaurants, the roasted carrot agnolotti at Grano Arso is nothing short of sensational. Keep in mind that you have the world-renowned Goodspeed Opera House’s local Norma Terris Theatre, an underrated gem that shows Broadway-quality shows. If you want to stretch a bit, the hiking trails in the Cockaponset State Forest will come in handy.

Guilford

If your idea of a perfect getaway includes a beautiful landscape with a sumptuous shoreline and lovely rural views, you should start making plans with Guilford, a cute little town with an awesome Town Green. The area around the beach features nice houses by the water, while other places are enchantingly calm, slow, and incredibly laid back. The lobster and crab cakes at Prime on Whitfield are out of this world, and you should give them a try if you want a feel of the town’s culinary landscape. Also, trust Guilford to blow you away with its great trails and lots of cool coastal nooks. Speaking of trails, there is Timberlands, a great place to hear the leaves rustling and the wind blowing, and Bluff Head Trails, which features a great view of Hartford and the sound.

Essex

Essex is surrounded on three sides by water. Therefore, if looking for a water-themed getaway, the experience that Essex provides is unmatched. Although it has been a while since Essex was named the Best Small Town in America in Norman Crampton's 1995 book, the town still retains many of the essential features that helped it grab the spotlight. It is on the west bank of the Connecticut River, a waterway that gives it a whisper of countryside elegance. You will want to mill around the Town Dock and the Connecticut River Museum, which features an amazing turtle submarine and interesting facts about the longest river in New England. Situated on the water, this museum offers relaxing boat rides with nice breezes and views. Also, Essex is home to one of the oldest continuously operating inns in the United States: The Griswold Inn. It has been welcoming travelers since 1776, the same year that Thomas Jefferson wrote the Declaration of Independence.

Old Saybrook

Old traditions. Old books (Think of the Classics). Old Saybrook. The past often has a hold on us that is just quite difficult to shake off. Although it does not have the fame of St. Augustine, Florida, Old Saybrook, the original site of Yale College, has a long history that dates back to 1635. Nestled where the Connecticut River meets the Long Island Sound, this historic town offers beautiful shores, two public beaches, several boat marinas, and an eclectic mix of restaurants. If you want to spend your day with putters and tees, the Fenwick Golf Course is beautiful and one of the oldest courses in Connecticut. Check out Rosemary & Sage, an adorable space that serves delicious broiled scallops and great cocktails. Plus, Katharine Hepburn Cultural Arts Center is a cozy and comfortable venue for a live performance.

The Takeaway

If you are looking to wind down in a tranquil setting that serves a mix of outdoor beauty and modern elegance, Connecticut has options that will leave you in awe. In some of these small, charming towns, where cobblestone streets meet coastal breezes, almost every corner is a photo op. You will enjoy exploring Indie bookstores, scenic trails, historic architecture, and small mom-and-pop shops.