7 Best Connecticut Towns For A Weekend Trip

While the New England state of Connecticut sits just over an hour’s drive from metropolitan areas like New York City, it’s certainly filled with enough attractions and activities to compete. With many beautiful landscapes, shops, and historical sites in the area, it is also a prime spot for a weekend getaway. For decades, visitors from the surrounding metro areas like New York and Boston have been making the scenic trip to escape to Connecticut when they need a break from the city’s hustle and bustle. These towns make the perfect weekend trip thanks to their ability to easily accommodate any traveler and let you take the voyage you need to enjoy the weekend.

Mystic

Mystic, Connecticut, is less than three hours from New York City and less than two hours from Boston, making it a viable weekend getaway. During the summer and fall, guests can enjoy cool breezes off the ocean and vibrant foliage as backdrops for all their activities. Those looking to continue their outdoor experiences can take their boat on a guided tour with Mystic Boat Adventures for a full look at Mystic’s natural landscape.

Besides exploring the outdoors, indoor activities are plenty and exciting. Locations to explore include the Mystic Seaport Museum, where you can explore an old ship, view ancient carvings, and learn about invertebrates. The Mystic Aquarium is also an exciting place to check out, with exhibits on whales, penguins, and sea lions, giving visitors more knowledge of the surrounding sea life. With much to explore, Mystic guests can take a short rest at one of many accommodations available in town, including The Whaler's Inn, which is located close to all of Mystic's most popular attractions. Chain options like The Spark by Hilton Mystic Groton offer reliable and affordable rooms within a two-mile drive of downtown.

Westport

Westport is a small town community located on the beautiful Long Island Sound. Touting gorgeous beaches and water views, beaches like Compo Beach are a great place to begin your getaway. Unlike other towns, only some beaches can be accessed with a daily pass, while others require a Town of Westport Emblem. Besides its beach community, Westport is full of cultural activities, making it a versatile place to visit. Enjoy a play at the Westport Country Playhouse, where local playwrights, actors, and designers showcase their talents. Visitors can also explore the Westport Museum for History and Culture, where you can view exhibits or sign up for a walking tour of the area.

Like many coastal towns, the accommodations are just half the fun of your weekend getaway. The Inn at Longshore offers gorgeous water views, comfortable rooms, and excellent dining options like Bartaco or The Boathouse at Saugatuck, where you can enjoy delicious coastal cuisine that makes the area famous.

Essex

Essex is a wonderful destination for a quintessential New England long weekend on the Lower Connecticut River. Essex Village's Main Street is a prime place to begin your journey, with plenty of cute locales and eateries. Along these shops, locations like The Connecticut River Artisans are a favorite for finding unique handcrafted goods, while Essex Coffee and Tea Company offers some much-needed caffeine and treats.

Once you’re ready to learn and explore, locations like the historic Ivoryton Playhouse are a must-visit, where you may catch one of their famed seasonal live performances. The Essex Steam Train & Riverboat Museum provides another significant glimpse of the town’s past with unforgettable steam train rides and riverboat cruises. There’s no better place to stay than Griswold Inn to complete your historical experience. Established in 1776, this historic inn combines classic vintage charm with modern amenities in the center of Essex.

Madison

Madison, located in Southern Connecticut on the Long Island Sound, is a quaint and relaxing town ready for your weekend escape. Tranquill beaches like Surf Club Park are open to the general public and include various flex spaces like picnic areas, volleyball courts, and boating areas. To get the ultimate New England charm, Madison’s beaches offer some of that coastal charm. Accommodations like the Madison Beach Hotel boast breathtaking water views, dining, and a spa that lets you enjoy everything about being seaside.

Downtown Madison offers adorable spots, such as the recently renovated RJ Julia Independent Booksellers and Madison Cinema, which has received numerous awards and accolades. Those looking to grab a souvenir or spend time shopping will find numerous boutiques and locales filled with unique knickknacks and relics. After exploring downtown, settle for authentic Italian cuisine at the highly recommended Cafe Allegre for a relaxing and delicious end to your day.

Chester

Originally planned as a shipbuilding community and mill town, Chester blends its rich heritage with modern-day amenities. Filled with renovated and restored colonial-era buildings, Chester is the perfect place to experience some of this history firsthand during a weekend away. Yearly, tourists are captivated by the town’s most famed attractions, including The Old Town Hall, Norma Terris Theatre, Chester Museum at the Mill, Villa Bella Vista, Jonathan Warner House, and the Charles Daniels House. During your weekend travels, Sunday markets, which include lively bands, food trucks, and many local treasures, help make Chester the place to be.

Visiting Chester for the weekend also means enjoying updated country residences like The Guest House, which offers cozy accommodations and healthy meals throughout the day. With a charming and small-town feel, there’s no better place to feel at home than a Chester accommodation.

Old Saybrook

Old Saybrook is a picturesque coastal town nestled where the Connecticut River meets the Long Island Sound. With a rich history on display, weekend visitors can enjoy activities like the Old Saybrook Walking Tour, where guests will learn all about the town’s past, which dates back to 1635. Sites like the Katharine Hepburn Cultural Arts Center are great for catching an evening musical performance. Visitors can enjoy the Katherine Hepburn Museum, which honors the life of former Old Saybrook resident and renowned actress Katherine Hepburn. Historic cemeteries, railroad stations, and buildings date back to revolutionary times, giving visitors an even better glance at the history that makes Old Saybrook renowned.

While mostly popular during the warmer months, Water’s Edge Resort & Spa offers a year-round relaxation spot for those looking to indulge during their weekend away. Updated rooms with water views, house rentals, a pool, a spa, and dining await those looking to take a break from the busyness of the city. Complete with all of the modern amenities you could ask for, there’s no doubt Water’s Edge Resort & Spa will be a highlight of your travels.

Cornwall

Cornwall is the Connecticut weekend trip for those who enjoy the great outdoors. Activities like hiking the Pine Knob Loop Trail in nearby Sharon or rafting on the Housatonic River make Cornwall the perfect active weekend away. Seasonal events like the Cornwall Turkey Trot make for ideal physical activities that test everyone’s physical endurance. While full of outdoor physical activities, Cornwall also has plenty of fun and relaxing events, such as the Cornwall Days, where live music meets art and food in one eclectic event.

After a long day of walking, hiking, or running, spots like the Cornwall Inn provide comfortable lodging with country views that will act as the perfect resting spot for your weekend away. While nestled in the quaint countryside of town, Cornwall Inn also offers guests the chance to be close to the downtown area, where you can see more of the town’s charm.

Whether you seek a quick seaside escape in the warmer months or a chance to soak up the fall and winter colors and flavors, you can't go wrong with a weekend trip to Connecticut. With many beautiful beaches, homegrown locales, and historical landmarks, you will have plenty to keep you busy for a weekend or longer if you choose. Full of activities for those of all ages, there’s something for everyone to enjoy in the Nutmeg State. Regardless of whether you’re traveling from near or far, the quaintness and charm of these Connecticut towns are more than enough to captivate travelers.