The 12 Most Charming Small Towns in Connecticut

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 and water sports to name a few).

Places to stay:

• Antique School House (2 guests): $124/night
• Mountain View Getaway (5 guests): $266/night
• The Beehive Cottage (8 guests): $75/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.

Places to stay:

• Renovated One Bedroom Getaway (2 guests): $150/night
• Seaside Getaway (4 guests): $300/night
• Private Carriage House (5 guests): $250/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 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.

Places to stay:

• New England Beach House (3 guests): $242/night
• Brand New Beach House (6 guests): $414/night
• Beach Cottage next to Silver Sands State Park (8 guests): $225/night

This town in Fairfield County 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.

Places to stay:

• Elegant Country Estate Guest House (4 guests): $155/night
• Romantic Riverfront Farm House (6 guests): $161/night
• Peaceful Pinewood Retreat (7 guests): $314/night

What do PT Barnum, Meg Ryan and Duracell batteries all have in common? A town called Bethel, it turns out. A hop, skip and a jump from New York City, this Fairfield County winner is very small and oh-so quaint. Bethel’s downtown may be pint-sized, but it’s nothing to shake a stick at—you’ll find boutiques, antique stores and top-notch farm to table eateries there—and the surroundings are ripe with opportunities for farm visits and outdoor adventures. Plus, some good news for film buffs: Bethel has a super cool indie movie theater and serves as the recurring host of the Connecticut Film Festival.

Places to stay:

• Elegant Country Estate Guest House (4 guests): $155/night
• Direct Waterfront on Candlewood Lake (6 guests): $950/night
• Waterfront Lake House (7 guests): $525/night

First settled in 1692, the rural town of Chester is a welcoming oasis, tucked into the scenic hillside of the Connecticut River. Here, the backdrop of your day-to-day will include marinas, lakes, brooks and breathtaking waterfalls...oh, and thousands of acres of state forest, too. Although this Connecticut town is pleasantly quiet and old-timey, it’s certainly not stuck in the past: Once a shipbuilding and mill town, Chester is now a magnet for creatives and boasts many art galleries, as well as the Norma Terris Theater—the second stage of the world-renowned Goodspeed Opera House.

Places to stay:

• Saybrook Point Cottage (2 guests): $150/night
• Charming Chester Retreat (4 guests): $138/night
• Tuscan Villa (6 guests): $400/night

This farming community features picturesque landscapes—both farm and forest—historical architecture and plenty of culture. Washington’s proximity to New York City makes it a popular retreat, but the total population of the town is only 4,000—so you can certainly count on a quiet, country lifestyle here. Like some other Litchfield County gems, Washington has the benefit of being located at the foothills of the Berkshire Mountains, where residents can enjoy the scenic beauty of numerous nature preserves, hiking trails, lakes and, of course, easy access to the slopes for winter skiing.

Places to stay:

• Private Annex (4 guests): $250/night
• Dainty New Preston Cottage (6 guests): $313/night
  
• Waterfront House on Lake Waramaug (12 guests): $990/night

The town of Essex sits pretty in Middlesex County—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.

Places to stay:

• Saybrook Point Cottage (2 guests): $150/night
• Renovated Barn (4 guests): $468/night
• Sunny Cottage With Private Beach (6 guests): $190/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.

Places to stay:

• Beachside Studio Vacation (2 guests): $271/night
• Ennis Cottage (4 guests): $206/night
• Beautiful Beach House With Private Beach Access (8 guests): $234/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.

Places to stay:

• Cute Cozy Cottage Studio (4 guests): $195/night
• Cozy Cottage in Westport (6 guests): $235/night
• Exquisite Westport Manor (12 guests): $1,500
  

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.

Places to stay:

• Lakefront Cottage (2 guests): $287/night
• The Sunny Cove Cottage on Coventry Lake (4 guests): $219/night
  
• Pet-friendly Waterfront Lake Cottage (7 guests): $195/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 a cascading waterfall along with 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.

Places to stay:

• Modern Cottage on the Housatonic River (2 guests): $252/night
• Private Kent Getaway With Views (4 guests): $270/night
• Farm House in the Village of Kent (6 guests): $204/night