10 Of The Most Adorable Small Towns In Connecticut
Sometimes called the Nutmeg State, sometimes the Constitution State, Connecticut offers a balanced blend of modern attractions and historic charm. As part of New England, it sits on the northeast coast of the United States between New York to the west, Massachusetts to the north, and Rhode Island to the east. On the southern boundary, is Long Island Sound, an estuary of the Atlantic Ocean.
From coastal getaways to historic sites and live theater, these small towns offer something you won't find anywhere else.
Chester
What could be more adorable than a town with a squirrel for a mascot? In the early 1970’s, the official seal of Chester was created depicting a cedar sprig and two running squirrels, and the critter has since become somewhat of a marketing and promotional icon. But rest assured, this isn't the only animal you'll see on a visit to Chester. Chakana Sky Alpacas is a sanctuary raising alpacas in a way that honors Indigenous peoples and animals of the Andean region. You can book a tour online, or stop in to browse their store, which features a range of products including clothing, accessories, yarn, and toys.
The Wayfinder Society is another unique shopping experience. Here, you will be greeted by Betsy, canine extraordinaire, and inside you will find all sorts of treasures and curiosities, from crystals and gems to handcrafted gifts from around the world. Lori Warner Studio/Gallery & Swoon Boutique is a must see for any art lover with its collection of one-of-a-kind ceramics, furniture, jewelry, and fine art.
Guilford
Guilford is an adorable town by the sea, steeped in rich history. The Henry Whitfield State Museum is the perfect place to start your visit. The museum features New England’s oldest stone house and dates back to 1639. You can also read more about this town at the Guilford Free Library. Serving the community since 1737, it houses the Edith B Nettleton Historical Room, named in honor of the town’s first librarian, and hosts a number of events, such as readings, guest speakers, and plenty of programming for kids. A visit to this adorable seaside town would not be complete without a delicious lobster roll, and Guilford Lobster Pound does not disappoint. “Fresh off the boat, since 1991,” you can get live lobsters to go or have a meal on their dockside patio with perfect harbor views.
Madison
Right next door to Guilford and named after President James Madison, the town of Madison features adorable boutiques such as RJ Julia Booksellers & Café, and specialty shop, Savvy Tea Gourmet. The Madison Farmers’ Market on the Historic Town Green features vendors such as Four Root Farm for organic vegetables and flowers, and MarnaRoons for artisan coconut macaroons. Delicious!
For a different view, visit Hammonasset Beach State Park's sandy beach, perfect for camping, bird watching, biking, or a walk along the boardwalk. Wrap up your day at the casual Lenny & Joe’s Fish Tale Restaurant for a plate of shrimp, scallops, and other fresh, local seafood.
Mystic
In Mystic’s loveable and eclectic downtown waterfront, you will find one-of-a-kind shops like The Bees Knees, a boutique for fun home décor items, Hang the Moon for women’s gifts and jewelry, and Mystic River Chocolate Café, for a wide range of tasty treats, including chocolate beer (yes, you read that right). Do not miss the Mystic River Bascule Drawbridge. Built in 1922, this beloved landmark connects the Groton side of town with the Stonington side and, of course, allows boat traffic through. Just a few miles from downtown is Denison Homestead. This preserved family farm is 300 years old and features the 1717 House Museum, Denison Pequotsepos Nature Center and Denison Farmers Market.
New London
New London is a deep-water port town with a mix of cultures. The Cultural District is an eclectic mix of locally-owned shops, galleries, and restaurants along the Thames River. Explore the Thames River Heritage Park with a boat tour or the hop on-hop off harbor cruise which runs between downtown New London, Fort Trumbull, and Thames Landing in Groton. The Black Heritage Trail celebrates the strength, resilience, and accomplishments of the region's Black community, and the Shaw Mansion built in 1756, currently houses the New London County Historical Society.
For fun in the sun, Ocean Beach Park has something for everyone. Enjoy treats from Sandbar and Boardwalk Creamery, and check out the amusement rides, arcade, mini-golf, and waterslides, then stick around for live entertainment on the boardwalk stage.
Niantic
Niantic is a family-friendly coastal village in East Lyme, Connecticut, with sandy beaches and ocean vistas for days. McCook Point Park has two such beaches with picnic areas and a children’s playground, as well as outdoor concerts in summer. If a walk is what you are looking for, Niantic Bay Boardwalk is for you. This mile-long stretch promises an incredible view of Long Island Sound from Cini Memorial Park at one end to Hole-in-the-Wall Beach at the other. On the corner of Hole-in-the-Wall Beach and Main Street you will find Gumdrops and Lollipops. You can't go wrong with homemade fudge, chocolates, ice cream, or a refreshing vintage soda.
Norwich
Dubbed the “Rose of New England” for its rolling hills that resemble rose petals, Norwich is located where the Yantic, Quinebaug, and Shetucket Rivers converge to form the Thames River. You can literally stop to smell the roses at Mohegan Park & Memorial Rose Garden, particularly between late June and July, when the blooms are at their peak.
Norwich is also known for its trails. Heritage Trail is a 2.8-mile roundtrip walk along the Yantic River connecting downtown Norwich to the Uncas Leap Heritage Area which features the Yantic Falls. Perhaps one of the most adorable things about Norwich is that you can sleep in a treehouse! Water Forest Retreat is a secluded tiny home located on 56 acres of forest that includes a brook, waterfall, marsh and pond.
Old Saybrook
Old Saybrook is just a quick trip from Boston or New York with a picturesque town center. From unique women’s clothing and accessories at Pearls & Plaid to the opportunity to take in a show at The Katharine Hepburn Cultural Arts Center (or, The Kate, as it's affectionately called), Main Street earns its spot on the to-do list. You can continue your pursuit of culture with The Trove, an antique shop where every piece has a story.
For some light recreation, head to Harvey's Beach for boating, fishing, and swimming, with lifeguards on duty from Memorial Day through Labor Day. One of Connecticut's best beaches, you'll find white sand and shallow water, as well as sandbars at low tide.
Wethersfield
Connecticut’s largest historic and cultural district is in its “Most Auncient Towne,” Wethersfield. Here, they have been preserving authentic New England heritage for nearly 400 years. You can experience these deep roots with the Wethersfield Heritage Walk, a 3-mile self-guided tour with maps and brochures available at Keeney Memorial Cultural Center, as well as several locations around town.
After soaking in all that heritage, you can take a break at Mill Woods Park. Featuring a beach, outdoor swimming pool, off-leash dog park, fishing pond and even bocce courts, there is bound to be something for everyone. If all else fails, have a picnic by the water and let your mind do the wandering. Silas W Robbins House is a historic bed and breakfast when it's time to call it a night, and you might even get the feeling you've seen this adorable house before; the home was featured in the 2018 film “Christmas on Honeysuckle Lane.”
Woodbury
Woodbury is known as the Antiques Capital of Connecticut. Walk along Main Street's Antique Trail and you will see masterfully restored homes built as far back as the town's settlement in 1673. You will find American antiques and fine art at Kocian DePasqua Antiques, vintage treasures with a custom flair at Villa Vintiques, and a fine collection of art, furniture, and porcelain at Madeline West Antiques.
To fuel your shopping spree, make sure you stop into Sumpin Sweet Treats for pastries and other sweets made from scratch. After a day of treasure hunting, you may need a little grounding and balance. You can find this at Salt of the Earth Therpeutic Spa, offering self-care services in a salt room, salt cave, and lagoon room for maximum effect.
From Chester's charming squirrel mascot and the rich history of Guilford and Wethersfield, to antique shopping in Woodbury and homemade candies in Niantic, this corner of New England is a haven for the senses. Whether you're seeking seaside fun along Long Island Sound or exploring centuries-old trails and museums, there's something for everyone in Connecticut's adorable small towns.
