The 15 Most Charming Small Towns in Connecticut

• Things to do: hiking, biking, fishing, water sports, skiing 
• Places to stay: West Cornwall Cabin ($212/night), Mountain View Getaway ($272/night), The Beehive Cottage ($90/night)

Bordered by the Housatonic River and settled at the foothills of the Berkshire mountains, this Litchfield county gem boasts loads of natural beauty to boot. In fact, Cornwall is said to be the greenest town in the state (we’re talking about actual trees, not environmentalism)—an accolade that can be attributed to the large portion of the gorgeous Mohawk State Forest that it contains. The town has plenty of historical character—it’s home to one of only three surviving covered bridges in the state—but modern day-Cornwall owes much of its appeal to the abundance of recreational activities it has on offer (hiking, biking, fishing, water sports and winter skiing, to name a few).

• Things to do: historic sights, seaport museum, aquarium 
• Places to stay: Renovated One Bedroom Getaway ($164/night), Seaside Getaway ($195/night), Private Carriage House ($293/night)

Mystic—a town situated on Mystic river, a body of water that flows into the Long Island sound—became an important ship-building center not long after its founding in the mid-17th century. Today, however, the town is best known for its archetypal New England vibe, lowkey tourist attractions (i.e., an aquarium, seaport museum and lovely historic district)...and the ‘80s classic Mystic Pizza, of course. Indeed, this charming seaport hits the ‘small town, but not snoozefest’ nail on the head, making it a happy medium between urban dwelling and country life.

• Things to do: historic sights, boutique shopping, water recreation 
• Places to stay: New England Beach House ($212/night), Breathtaking Bungalow ($148/night), Beach Cottage next to Silver Sands State Park ($208/night)

This quiet beach town is just a stone’s throw away from New Haven, but you could mistake it for a humdrum suburb at first. Never mind the strip malls on the outskirts of this quaint New England spot, though—once you discover Old Town Milford, a historic district complete with cute, quirky shops and good eats, you’ll experience the real charm of this laid back beach town. Aside from ample opportunity for water recreation, Milford also boasts a seriously impressive “town green,” the second longest in New England, that features multiple memorials—yet another nod to the town’s rich history.

• Things to do: historic sights, recreational parks, biking trails 
• Places to stay: Elegant Country Estate Guest House ($155/night), Romantic Riverfront Farm House ($275/night), Peaceful Pinewood Retreat ($315/night)

This town in Fairfield County, CT is on the upswing in terms of population growth, being that it’s within easy driving distance of Bridgeport, New Haven and New York City. That said, Monroe has maintained its small-town feel and historical character. Named after James Monroe (i.e., the country’s fifth president), this Connecticut town feels like a blast from the colonial past. However, you don’t have to be into historical reenactments to enjoy Monroe: This one boasts a number of scenic recreational parks (Webb Mountain, Wolfe Park. Great Hollow Lake) and a ton of bike paths to boot.

• Things to do: shopping, natural attractions, top-notch dining 
• Places to stay: Saybrook Point Cottage ($189/night), Renovated Barn ($443/night), Sunny Cottage with Private Beach ($171/night)

The town of Essex sits pretty in Middlesex County, CT—surrounded on three sides by water and located just miles away from where the Connecticut River empties into the Long Island Sound. In the town center, striking Colonial and Federal-era buildings line the streets, some of which house modern amenities. (Think, a funky-cool coffee shop that makes a mean latte, a carefully curated toy shop and a killer seafood restaurant within walking distance.) Yep, this tiny, tree-lined harbor village can be explored on foot; after that, the surrounding park and conservation lands are sure to keep you busy.

• Things to do: historic sights, beaches, hiking, water recreation 
• Places to stay: Beachside Studio Vacation ($329/night), Ennis Cottage ($199/night), Beautiful Beach House with Private Beach Access ($250/night)

Located just six miles east of New Haven, you can file Branford under ‘the burbs.’ But not so fast: This idyllic town is a far cry from the bigger city nearby—and instead of strip malls and business parks, this suburb boasts 20 miles of pristine beach, historic homes, scenic roads and easy cruise ship access to the Long Island Sound archipelago known as the Thimble Islands. (Note: Sailing opportunities abound.) As for outdoor recreation, check out the Branford trail—a 30-mile-long circular trail that takes you on a scenic tour of the town’s lakes, woodlands and wetlands.

• Things to do: cultural attractions, historic sights, beaches 
• Places to stay: Cozy Country Cottage ($225/night), Cheerful Residential House ($225/night), Westport Paradise ($370/night)

This charming Connecticut town is among the better-known on the list, primarily as an escape for New York City’s well-to-do. That said, this tight-knit community prides itself on negotiating and reconciling its small-town past with the affluence of its present—a give-and-take that accounts for the quaint, but cosmopolitan vibe of Westport. The Westport Country Playhouse and Westport Museum of History and Culture are just a couple of the town’s enticing attractions for creative types. Bottomline: If you’re looking for a compromise between urban and rural life, and can afford the happy medium, Westport will fit the bill.

• Things to do: historic sights, natural attractions, hiking, outdoor recreation 
• Places to stay: Lakefront Cottage ($247/night), The Sunny Cove Cottage on Coventry Lake ($224/night), Classic Lake Cabin ($155/night)

Tranquil country living coupled with a particularly stunning historic district set Chaplin, a town in Windham County, apart from the rest. This one is entirely unpretentious and—with a population of less than 3,000—very quiet. (In fact, its location in Northeast Connecticut is known as ‘Quiet Corner.’) Don’t expect a foodie scene here, or any of the other trappings of social-media-city-life for that matter...that said, you’d be hard-pressed to find a more beautiful place to go somewhat off the grid.

• Things to do: natural attractions, historic sights, breweries 
• Places to stay: Artistic Concered Barn ($470/night), Private Kent Getaway With Views ($285/night), Victorian Guest Suite ($144/night)

The Litchfield County town of Kent cozies up with the New York border...and chances are, residents aren’t mad about it. Living in Kent means you can book it to NYC in less than two hours, while enjoying considerably more scenic stomping grounds. For starters, there’s Kent Falls State Park, which features many cascading waterfalls along with cute picnic spots and probably forest pixies. (Who knows?) Not to mention Bull’s Bridge—a historic wooden behemoth that arcs across the majestic Housatonic River. Plus, the charming ‘downtown’ area offers everything from quality food to independent bookstores. Oh, and there’s craft beer nearby, too—if you decide to venture out to Kent Falls Brewing, that is.

• Things to do: cultural attractions, historic sights, natural attractions, beaches
• Places to stay: Belle Vue Cottage ($158/night), The Cottage ($93/night), Cozy Loft Getaway ($171/night)

Old Saybrook was once home to Oscar Award-winning actress Katherine Hepburn and the town’s top attraction is a cultural arts center bearing her name. Beyond that, this gem on the Long Island Sound is known for its unparalleled beauty and New England charm. (Old Saybrook is pretty much the definition of picturesque.) The town also boasts a bustling Main Street, replete with restaurants, boutiques and antique shops, and is in close proximity to quite a few natural attractions—most notably Rocky Neck State Park, a perfect place for birding and hiking, as well as the pristine Harvey’s Beach, which is a family-friendly coastal spot with soft sand and placid, shallow water.

• Things to do: beaches, natural attractions, hiking 
• Places to stay: The Barn by the Sound ($250/night), Beachy & Bright Carriage House ($150/night), Seaside Oasis in Madison ($600/night)

Another spot on the Long Island Sound—Madison is prized for its coastal beauty and easy access to destinations for nature-lovers, like the Meigs Point Nature Center and the Shoreline Greenway Trail, a mile-long scenic trail for strolling and biking that attracts locals and tourists alike. When you have had your fill of outdoor recreation, be sure to spend some time downtown to browse the bookstores and assortment of cute boutiques or catch an indie flick at Madison Art Cinema.

• Things to do: beach and boardwalk, children’s museum, bars and restaurants 
• Places to stay: Retreat Home in Beach Community ($75/night), Townhouse in Niantic ($145/night), Coastal Getaway with Porch ($158/night)

In case you missed it, the Long Island Sound is the place to go for a serene visit to a charming seaside village. Niantic, yet another fine option in the region, boasts a lovely bayside boardwalk and (like the neighboring town of Old Saybrook) close proximity to Rocky Neck State Park where you can while away the hours whilst taking in the natural beauty of your surroundings. Best of all, Niantic is an excellent destination for families, since it’s home to the hugely popular Children’s Museum of Southeastern Connecticut—a 5,000-square-foot attraction that promises hours of interactive and educational fun for the younger ones in your party.

Which Connecticut Towns Are Most Like Stars Hollow? 

So you’re a Gilmore Girls fan and are wondering which towns feel most like you’re stepping onto the set of your favorite TV drama? The show’s creator and executive producer Amy Sherman-Palladino shared in an interview that the fictional “Stars Hollow” from Gilmore Girls—a picturesque place where everybody knows your name and your business—was inspired by a visit she took to the small town of Washington, CT (see #7 on our list), where she and her husband stayed at a charming inn and thoroughly enjoyed the New England vibes. Suffice it to say that if you’re looking to channel your inner Rory or Lorelei Gilmore, many of the towns on our roundup are a good fit—but probably none better than Washington.