The 30 Most Charming Small Towns in Connecticut
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Connecticut is home to many wonderful things. Nestled on the New England stretch of the East Coast, it's a state that has both beaches and foliage, adorable B&Bs, some of the most festive Christmas towns in the country, and a vibrant art scene. As the Constitution State, it's also an excellent place to go if you love Revolutionary War history. What Hamilton fan doesn't want to see where Washington met with Rochambeau?
Perhaps the reason we most love it, though, is its seemingly endless supply of enchanting small towns—including, yes, the very one that Amy Sherman-Palladino herself confirmed inspired Gilmore Girls's Stars Hollow. Then you have coastal towns with spas on the shoreline, inland villages with state parks perfect for hiking, hamlets with restaurants awarded by both James Beard and Michelin, and a town with so many antiques stores there's an official "Antique Trail." Plus, the shopping can't be beat—especially if you're in the neighborhood of Connecticut's answer to Rodeo Drive.
Scroll on for 30 of our favorite cozy and welcoming Connecticut towns that will make you feel like Lorelai and Rory.
Greenwich
The largest town on Connecticut's "Gold Coast," Greenwich features superb arts and cultural attractions, including the Bruce Museum, four beaches along the Long Island Sound, year-round festivals that cater to various interests (like the annual Greenwich Concours d'Elegance), and the iconic Greenwich Avenue shopping neighborhood (which some have likened to Rodeo Drive). So, skipping it? Big mistake. Huge.
Stonington
The charming seaside village of Stonington, located in the southeast corner of the state, is known for its mile-long beaches, historic seaside homes, and eclectic shops and boutiques. It's also home to two top vineyards: Stonington Vineyards and Saltwater Farm Vineyard.
Washington
Washington has the best of both worlds: a small-town vibe with a very vibrant cultural scene. With a backdrop of the Berkshire Mountains—which truly come alive in the fall—the town is blessed with the dreamiest natural surroundings, including Lake Waramaug and the Shepaug River. There's also the absolutely stunning Mayflower Inn & Spa, even has a European-inspired garden. But the ultimate reason it made our list? Amy Sherman-Palladino herself confirmed that Washington served as the inspiration for Gilmore Girls's Stars Hollow. (The town even hosts an annual Gilmore Girls festival.) Peek inside The Mayflower—where Amy herself stayed—and you might just see Lorelai and Sookie bantering in the corner.
Mystic
Mystic is truly beloved—and not just because of the Julia Roberts classic Mystic Pizza. Set on the majestic Mystic River, the seaside village is teeming with that classic New England aesthetic, charming shops, and two of Connecticut's most-visited attractions: the Mystic Seaport and Mystic Aquarium. Plus, it has firmly established itself as a foodie haven, with world-class eateries run by multiple James Beard Award nominees, including the Shipwright's Daughter, a local gem within the darling Whaler's Inn that celebrates New England's fresh food heritage.
New Canaan
New Canaan does have an adorable downtown, but don't sleep on its arts attractions: Grace Farms and The Glass House. The former offers workshops, concerts, and more on its stunning 80 acres of publicly-accessible landscape. House, meanwhile, is a National Trust Historic Site with a permanent collection of 20th-century paintings and sculptures, plus rotating temporary exhibitions (which in the past have included works by Max Strang, Mark Mennin, and Sekou Cooke).
Old Saybrook
One of Connecticut's oldest towns, Old Saybrook offers a trove of historical and cultural sites—and one of the most beautiful beaches in the state to boot. One of the town's main features is Saybrook Point Resort & Marina, a family-owned, AAA Four Diamond–rated property with luxury accommodations and an award-winning restaurant, Fresh Salt. (Just as good as the food? The ocean views.) If you're a theater and film buff, stop by the Katherine Hepburn Cultural Arts Center—aka the Kate—a theater and museum honoring the late actress, the town's most celebrated resident.
Simsbury
Simsbury is the quintessential New England town, complete with a picturesque downtown filled with historic houses, fine restaurants, coffee shops, and small boutiques. The town is also home to Talcott Mountain State Park, one of the state's top hiking destinations. When you visit, make sure to include a stop at the Heublein Tower, a historic lookout spot that sits 1,000 feet high and offers unparalleled vistas.
Westbrook
Nestled on the banks of the Long Island Sound between New Haven and New London, you'll find Westbrook: a quaint shoreline town with all the beachy amenities. For water sports, zip over to Black Hall Outfitters, a full-service paddle sports center that rents canoes, kayaks, and stand-up paddle boards. But if it's relaxation you seek, there's only one option: Water's Edge Resort & Spa, one of the best in New England. Its vacation rentals have walkout access to the beach, plus there are four restaurants, live entertainment almost every night in the summer, and a full-service spa.
Milford
Take a walk on the charming side in Milford's downtown, with its bounty of breweries, restaurants, and water views. Like many Connecticut towns, there's also an outdoor draw: Silver Sands State Park, a public recreation space with beaches, dunes, restored marshland, and a 14-acre bird sanctuary. The town also makes for a pretty magical Christmas destination.
Kent
Kent features a superb balance of old and new, quaint and chic, and nowhere is that better on display than at the trio of boutique lodgings known as The Kent Collection. While the Victorian (pictured) is a historic classic, the Firefly Inn is an updated farmhouse-style inn, and the Garden Cottages are cozy and eclectic. There's also plenty to do and see in the great outdoors, including Kent Falls, the Appalachian Trail, and a beautiful covered bridge—one of many across the state.
Litchfield
A prime example of a late-18th-century New England town, Litchfield has a historic central green surrounded by attractive restaurants and shops. Combined with the Horse Crossing signs that line its outer roads, there's a real old-world vibe here. For a New American meal in a cozy atmosphere, stop by At the Corner, an adorable restaurant offering quite the selection of craft beers. For a bit more of a splurge, try the delicious West Street Grill, seen here.
West Hartford
Just west of downtown Hartford, West Hartford offers the best of both urban and suburban experiences. West Hartford Center has been the community's main hub since the late 17th century and features dozens of premiere dining destinations—including the family-run Peruvian restaurant Cora Cora, a semifinalist in last year's prestigious James Beard Awards competition. A visit wouldn't be complete without a stay at The Delamar (pictured), a beautiful boutique hotel with its own on-site restaurant and spa. If you're traveling with children, be sure to pencil in The Children's Museum too—it's a sure hit with hands-on exhibitions and live animals.
Niantic
If you love fishing—or are a local island lover—Niantic is the place as it offers you access to everything. Not only can you reach prime boating and fishing spots from Niantic Bay, but you're also just a quick cruise away from Plum Glut (10 miles), The Race (10 miles), Montauk (21 miles), and Block Island (27 miles). Of course, if you never leave the docks, the view's not too shabby either.
Woodbury
Known as the antiques capital of Connecticut, this charming New England town is filled with historic homes, antiques shops, classic main street attractions, and more. You're sure to find anything your antiques-loving heart desires in the Woodbury Antiques Trail's more than two dozen shops. When you've finished a day of shopping, head over to the Salt of the Earth Therapeutic Spa and unwind inside the salt caves.
Branford
Branford beckons residents and visitors alike with an array of events and attractions, including quite the range of breweries. (Stony Creek Brewery, Caius Farm Brewery, and Thimble Island Brewing Company, to name just three.) There's something just off the shoreline too: the Thimble Islands, an ideal setting for boating, kayaking, and fishing. And the town happens to look like this at Christmas. Swoon!
Farmington
You may have heard of Farmington as the home of Miss Porter's School, the elite prep school attended by Jackie O.—but there's much, much more to see and do here. Numerous parks and trails, the scenic Farmington River, and world-class museums (including the lovely Hill-Stead, seen here) abound—and there's plenty for sporty travelers to do like river tubing and cross-country skiing.
Wethersfield
One of Connecticut's oldest towns, Wethersfield is home to the state's largest historic district. Its classic, small-town main street has a country store, restaurants (including the Charles, pictured here), and shops—not to mention a charming B&B that has been the location for multiple Hallmark Christmas movies. History buffs, don't forget the Webb Deane Stevens Museum: It's where George Washington rendezvoused with the Comte de Rochambeau for the Wethersfield Conference.
Middletown
Middletown is a vibrant place with an incredible arts and culture scene—the center of which is its Main Street, where you'll find international cuisine, shopping, and entertainment. It's also where town celebrations, like the colorful Pride Parade, take place. If you're staying overnight, check in to the Inn at Middletown, a historic hotel offering 100 well-appointed, freshly renovated guest rooms and suites and an award-winning restaurant.
Old Lyme
Famous for its flourishing artists' community, Old Lyme was at the center of the American Impressionism art movement in the early 1900s. In the central village on Lyme Street, you'll find several private galleries, museums, and public buildings—including the Florence Griswold Museum (pictured here), the Lyme Art Association, and Studio 80 + Sculpture Grounds—that celebrate this heritage.
Madison
Madison is indeed a picturesque coastal town—just look at this photo—but it also features a pedestrian-friendly downtown with an award-winning bookstore, an art-house cinema, a tea emporium, coffee shops, cafés, restaurants, and boutiques. For access to a private beach, book a stay at the Madison Beach Hotel.
Woodstock
While Woodstock is considered part of Connecticut's "Quiet Corner," it's filled with culinary and cultural gems. It's known for its tranquility, pastoral aesthetic, and history—the latter of which is finely preserved at Roseland Cottage, aka "the pink house." (It's been painted at least 13 different shades of pink over its 160 years.) You can tour the home, learn about its history, and see how it's still actively contributing to the community today via its gardens and restoration efforts.
Essex
Set on the Connecticut River, the village of Essex has been continually recognized as one of America's best small towns—and who are we to argue? It offers an ideal blend of history, art, shops, and restaurants, making it a treat for locals and tourists alike. Visitors can stay at the Griswold Inn, which, fun fact, is one of the oldest continuously operating inns in the country. There's also the iconic Essex Steam Train & Riverboat, where you can take scenic train and boat rides along the Connecticut River Valley.
Darien
Much like its counterparts on this list, the waterfront hamlet of Darien—the smallest of the towns on Connecticut's Gold Coast—has an idyllic downtown. After basking on the impeccable beaches along the Long Island Sound, stop by Uncle's Deli for a sandwich, explore the nearby nature trails, and end the day on Post Road—where you'll find plenty of restaurant options, like the Goose, pictured here, next to the town clock.
Cornwall
One reason to visit Cornwall? Its classic covered bridge, the very stuff of rural Instagram fantasies. (It's an active one, though, so watch out for cars if you go to snap photos.) That said, ask any tristate snow bunny about the biggest draw, and you're sure to hear one answer: the Mohawk Mountain Ski Area, a hot spot for winter sports with a lovely chalet for those who prefer après activities.
Westport
What doesn't Westport have? There's a charming downtown (Church Lane is chock-full of restaurants), a beach (Compo Beach), a performing arts center (Levitt Pavilion), a state park (Sherwood Island), and a contemporary art museum (MoCA Westport). Don't miss the Collective West, a concept store dedicated all things haute, from fashion and jewelry to interior design, curated by Christian Siriano.
Morris
With its rich agricultural history, Morris is a beautiful bucolic destination for a relaxing countryside getaway. There's nowhere better place to unwind than Winvian, an extraordinary retreat with 18 cottages (including the Library Cottage, pictured here) and one grand suite, each one uniquely designed by 15 different architects. Winvian also features a 5,000-square-foot spa and a self-sustaining organic garden, so its restaurant's meals are crafted from the freshest local ingredients.
Chester
Art, history, music, theater, crafts, and cuisine are all on offer in Chester, located in the beautiful Connecticut River Valley. Catch a performance at the Norma Terris Theater, get your history fix at the Chester Museum at the Mill, take in the beauty of the Connecticut River riding the Chester-Hadlyme Ferry, or simply peruse the downtown's covetable stretch of shops and dining.
Collinsville
Collinsville has a robust shopping area. Fine jewelry? Antiques? Farm-grown veggies? Check, check, check! If you're feeling adventurous, head to the Farmington River Trail, former railroad tracks that have been converted to a walking and biking trail. It connects to several surrounding towns, giving you the opportunity to explore all the area has to offer—i.e., more small town cuteness.
Putnam
Built on the banks of the Quinebaug River, the town of Putnam is has an Arts & Al Fresco motif. That translates to a downtown with an assortment of restaurants, bars, cafés, art galleries, boutiques, and theaters—aka everything you'd want and then some. Vintage lovers will adore Antiques Marketplace, while farm-to-table foodies (including vegetarians) will be very well fed at Elizabeth's Farmhouse.
Bethel
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