The Best Small Towns in Connecticut for a Weekend Retreat
While parts of Connecticut are located just over an hour's drive from New York City, it is considered a New England state. With so many beautiful landscapes, adorable shops, and historical sites in the area, it is also an excellent spot for a quick weekend getaway. For decades, visitors from metro areas like New York, Philadelphia, and Boston have been hopping on trains and revving up cars to escape to Connecticut when they need a break. Discover the best small-town destinations for a weekend retreat.
Mystic
A town that became an icon after the 1988 film Mystic Pizza, Mystic, Connecticut, is located less than three hours from New York City and less than two hours from Boston. Visit in the summer or fall, and you can enjoy the cool breezes off the ocean or the vibrant foliage. One of the most popular spots for visitors is the Mystic Seaport Museum, where you can explore an old ship, view ancient carvings, and learn about invertebrates. If you are bringing the kiddos along, the Mystic Aquarium is an exciting place to check out, with exhibits on whales, penguins, and sea lions. Adults in town for weekends in the summer might want to drive their own boat on a guided tour with Mystic Boat Adventures.
A popular destination for weekend guests, Mystic has plenty of places to stay overnight. Those looking for an elevated experience might choose The Whaler's Inn, which is located close to all of Mystic's most popular attractions. You can also enjoy cozy amenities like soaking tubs and fireplaces. If you are looking for a familiar name, the Spark by Hilton Mystic Groton offers clean, affordable rooms within a two-mile drive of downtown.
Montville
Located in Southeastern Connecticut, Montville is located about three and a half hours from New York City and around two hours from Boston. It's gained increased popularity over the last three decades as the home of Mohegan Sun Resort and Casino. Here, you can catch a great act at Mohegan Sun Arena, shop, play golf, or dine at one of their seven restaurants. And if you are bringing the kids along, head to the arcade and hotel pools. Littles will also flip for the multi-level toy karting, trampolines, and axe throwing at Supercharged by Mohegan Sun, just down the road from the resort. Plenty of suites and standard rooms are available for your stay.
Four minutes away in nearby Oakdale, you can check out Nature's Art Village, which offers mini-golf, a Dinosaur Place with a Splash Pad, and adorable shops. Find unique jewelry at the Absolute Bead Shop, souvenirs at the Ancient Fossil Shop, or gifts at the Ageless Toy Shop. Whether you are looking for an action-packed weekend or a nature-inspired getaway, Montville provides all the activities and convenience you are looking for.
New Canaan
A popular suburb for commuters, New Canaan, is also a fantastic location for a peaceful weekend away. Escape the city bustle at the New Canaan Nature Center, where you will enjoy outdoor trails, butterfly gardens, and interactive exhibits. Or stop by The Glass House, which offers tours from April through December. You can view indoor and outdoor sculptures, nature paths, and the modern Glass House and Painting Gallery.
If traditional small-town shopping is your thing, you will love the charming downtown options in New Canaan. Find an imaginative game at the New Canaan Toy Store or memorabilia at Americana Memories. You can also enjoy an elegant meal at the award-winning Cava Wine Bar or the perfect burger at Cherry Street East. Moreover, the comfortable guest rooms at the Roger Sherman Inn will give you a convenient place to stay while you enjoy the area.
Old Saybrook
Old Saybrook is a picturesque coastal town located where the Connecticut River meets the Long Island Sound. If you are in town for the weekend, get your steps in with the Old Saybrook Walking Tour, where you will view the rich history of the city that was settled in 1635. You can view sites like the Katharine Hepburn Cultural Arts Center, which was initially built as a community theater in 1905. This is an excellent venue for catching an evening musical performance or viewing the Katherine Hepburn Museum, which celebrates the life of the world-renowned actress and Old Saybrook resident. You can also find historic cemeteries, railroad stations, and buildings like 286 Main Street, which is believed to have been built before revolutionary times.
If you are visiting during the warmer months, you will love the Water's Edge Resort & Spa, which offers updated rooms with water views, house rentals, a pool, a spa, and dining. You can also enjoy clean, affordable accommodations at the Quality Inn Old Saybrook. If you love waterfront dining, don't miss the seafood delights at Fresh Salt or the clam rolls at Skipper's Seafood.
Westport
Westport is a haven nestled on the Long Island Sound. Some of its beaches, such as Compo Beach, can be accessed with a daily pass, while others require a Town of Westport Emblem. While you are in town, enjoy a play at the charming Westport Country Playhouse, where local playwrights, actors, and designers showcase their talents. You can also visit the Westport Museum for History and Culture, where you can view exhibits or sign up for a themed walking tour of the area.
If you are looking for somewhere to stay, The Inn at Longshore offers gorgeous water views and comfortable rooms. You can also enjoy a delicious seaside meal at bartaco or The Boathouse at Saugatuck. Quaint shopping abounds in downtown Westport, where you can find healing beverages at Arogya Holistic Healing or delightful home furnishings at Ayr Barns. Located less than 60 miles from New York and 160 miles from Boston, you can leave after breakfast and enjoy all of the small-town charms of Westport by lunchtime!
New Milford
Gracing the banks of the Housatonic River is a rustic small town with a lively country feel. If you love the outdoors, lap up boating and fishing on Candlewood Lake or enjoy the playground and basketball courts at Emmanuel Williamson Park. The Village Green is the perfect setting for gatherings like the Annual Litchfield County Artisan's Festival, the Summer Concert Series, and the New Milford Lions Club Carnival. Tree lightings and carol sing-a-longs illuminate the neighborhood in the winter.
If you are in town for the weekend, cozy spots like the Homestead Inn B&B will provide you with a comfortable room and a tasty morning meal. Enjoy wholesome downtown shopping at places like the Villarina's Pasta Shop or the Roxbrook Farm Stand. The area is known for its locally sourced ice cream, as evidenced by the new Ice Cream Crawl taking place each summer. Check out Grass Roots Ice Cream or the Kimberly Farm Ice Cream Shop for authentic local flavor.
Chester
Chester, Connecticut, is home to Cedar Lake, where you can swim and picnic in the warmer months. This is also the time of year to enjoy First Friday strolls, which are monthly events when Chester Village comes alive with art exhibitions, restaurant specials, live music, and shops extending their hours. Sunday markets, which include lively bands, food trucks, and many local treasures, take place through October. Chester is also home to authentic cuisine that will delight your palate, including the homemade pasta at Grano Arso or the craft beer at Little House Brewing Company.
Visiting Chester for the weekend means enjoying updated country accommodations like The Guest House, which offers comfortable rooms, a fitness center, and three healthy meals a day. If you are looking for evening entertainment, appreciate a musical at The Terris Theatre. There are also shows by local musicians and talented playwrights from the area at the charming Chester Meeting House.
Mashantucket
The village of Mashantucket is best known as the home of Foxwoods Resort and Casino, where you can enjoy a hotel with a pool and full spa or a luxurious villa with butler service. Live shows, delicious restaurants, and gambling are also part of the regular entertainment. If you are bringing the family along, an arcade, bowling, and HighFlyer Zipline will keep them active and happy. In addition, Great Wolf Lodge, an indoor waterpark and resort, will be opening in Mashantucket in 2025.
Shoppers will find great deals on all of their favorite name brands at the Tanger Outlets at Foxwoods. Also close to the casino is the Mashantucket Pequot Museum & Research Center. Here, you can view permanent exhibits, dioramas, and interactive programs that explore the history of the Mashantucket Pequot Tribal Nation.
Cornwall
If you love the outdoors, Cornwall is the Connecticut weekend trip for you. Hike the Pine Knob Loop Trail in nearby Sharon or go rafting on the Housatonic River. You can also enjoy annual races like the Cornwall Turkey Trot. If you are a fan of downtown festivals, check out Cornwall Days in the warmer months, when live music, food vendors, and art line the streets with activity. The Cornwall Covered Bridge is also a popular attraction, as it is one of the last remaining covered bridges in Connecticut.
Spots like the Cornwall Inn provide comfortable lodging with country views that will leave you wanting to stay longer than the weekend. While there, uncover the local flavor downtown. These include the delightful bakery, savory sandwiches, and homemade ice cream at the Cornwall Market and the wine and beer at the Cornwall Package Store.
Madison
Madison is located in southern Connecticut on the Long Island Sound. Peaceful, pristine beaches like Surf Club Park are open to the general public and include picnic areas, volleyball courts, and boating areas. Downtown Madison provides plenty of adorable spots to visit, such as the intriguing RJ Julia Independent Booksellers and the cozy Madison Coffee House. Overnight accommodations include the luxurious Madison Beach Hotel, which boasts breathtaking water views, dining, and a spa. Or enjoy the homey lodging and a delicious breakfast at the Scranton Seahorse Inn. You could also check out the Beach Tree Cottages, an old 1940s seaside resort now offering seven cute and comfy cottages from May through October.
Whether you are looking for a quick summer seaside escape or a chance to soak up the fall colors and flavors, you can't go wrong with a weekend trip to the Nutmeg State. With so many beautiful beaches, homegrown businesses, and historical landmarks, you will have plenty to keep you busy for a weekend or longer. There are even copious activities for kids of all ages. Those living in the tri-state area won't need to travel far to feel like they have wandered into a storybook-worthy part of the world: a magical land called Connecticut!
