Summary

  • Key takeaways:
  • Connecticut offers a variety of beautiful small towns with charming natural and historic beauty, including Kent, Chester, and Essex.
  • These towns provide a range of activities such as hiking, visiting state parks, exploring local restaurants and shops, and enjoying the scenic waterfronts.
  • Each town has its own unique character and attractions, making them ideal destinations for day trips or longer weekend getaways.

Besides its delightful New England charm, Connecticut offers a lot of fun things to do that can be seen everywhere, from its picturesque beachy scenery to its forested hills and its rolling farmland to its mountains, rivers, and seaside waterfronts. And there’s no better way to appreciate the state’s signature beauty than by checking out one of its most beautiful small towns—here are some of the very best.

UPDATE: 2023/09/04 13:26 EST BY NICHOLAS MAYAMBA

Most Beautiful Towns In Connecticut To Visit

Connecticut is a lovely New England state with charming small towns that place tourists in the middle of nature. From lush forests to sprawling lakes, this updated article highlights the prettiest towns in Connecticut worth checking out.

Related: 10 Most Beautiful Hikes You Can Do In Connecticut

12 Kent

Kent Falls State Park in Kent, Connecticut, USA
Shutterstock / Ritu Manoj Jethani
Kent Falls State Park in Kent, Connecticut, USA

Famous for its fabulous fall foliage, Kent is a quaint Connecticut charmer whose lush scenery is a sight to behold—and not just when the leaves are at their best and brightest. A lovely town center completes this picture-perfect New England town, while a plethora of nearby outdoor attractions means there’s always something to see and do.

  • Things To Do: Macedonia Brook State Park; Kent Falls State Park; Bull’s Bridge; House of Books; Kent Falls Brewing Co.
  • Wine & Dine: Kingsley Tavern; Swyft; Sophie’s Restaurant & Bakery
  • Stay The Night: The Victorian; Fife Country Inn

11 Chester

Chester, CT
David Trinks on Unsplash
Chester, CT, USA

Its rolling hills and scenic Connecticut River setting make Chester a quaint rural retreat full of natural and historic beauty. But that’s not all: once a hub for shipbuilding and milling, the picturesque town is now home to an up-and-coming local art and culture scene that’s all Main Street USA charm.

  • Things To Do: Gillette Castle State Park; Pattaconk Reservoir Trail; Little House Brewing Company; Godspeed Musicals at the Terris Theatre; Chester-Hadlyme Ferry
  • Wine & Dine: The Village Bistro; Grano Arso; Thai Riverside
  • Stay The Night: Copper Beech Inn (10 minutes); Boardman House (15 minutes)

10 Westport

Riverfront Park is a beautiful place to visit for a picnic and a hike.
Via: Shandley McMurray
Riverfront Park is a beautiful place to visit for a picnic and a hike.

The coastal town of Westport is all seafront scenery and colonial charm—and perfectly placed for a road trip to the Big Apple (50 miles away!), It’s the perfect weekend getaway from the city. Brimming with small-town beauty, Westport also has plenty of attractions to entice vacationers who like their R&R with a side of creativity and culture.

  • Things To Do: Westport County Playhouse; Westport Museum for History and Culture; Compo Beach; Earthplace; Sherwood Island State Park
  • Wine & Dine: Rive Bistro; Little Barn; Pane e Bene
  • Stay The Night: The Inn at Longshore; Hotel Zero Degrees (10 minutes)

9 Essex

View of the Connecticut River Museum at Essex with trees surrounding it
Photo 262019582 © Wirestock | Dreamstime.co
Connecticut River Museum, Essex, Connecticut

Colonial charm meets waterfront beauty in the pretty Connecticut town of Essex. The perfect place for both day trips and (long) weekends, visitors will enjoy strolling the picturesque harbor, admiring the historic architecture, and enjoying the fun shops and restaurants in the town center of this cozy rural retreat.

  • Things To Do: Essex Steam Train & Riverboat; The Pratt House; Connecticut River Museum; Falls River Preserve; The Pratt House
  • Wine & Dine: Scotch Plains Tavern; Carlson’s Landing; Tap Room at The Griswold Inn
  • Stay The Night: The Griswold Inn; Old Lyme Inn (10 minutes)

8 Milford

Milford, Connecticut
Photo by Clay Banks on Unsplash
Sunrise at Walnut Beach in Milford, Connecticut

A charming historic district—including the second-longest green in New England—gives the seafront setting of Milford quintessential small-town vibes. Full of character and idyllic beauty, plenty of eclectic shops and eateries are here to keep visitors busy when they’re not out on the water (or simply admiring its beachy beauty).

  • Things To Do: Old Town Milford; Milford Historical Society House Tours; Silver Stands State Park; Eisenhower Park; The Coastal Audubon Center at Milford Point
  • Wine & Dine: Founder’s House Pub & Patio; Bonfire Grille; Bridge House Restaurant
  • Stay The Night: Homestead Inn; The Blake Hotel (20 minutes)

7 Wethersfield

The Hurlbut-Dunham House is a popular attraction in nearby Wethersfield, Connecticut.
Via: Shandley McMurray
The Hurlbut-Dunham House is a popular attraction in nearby Wethersfield, Connecticut.

An idyllic natural setting complete with tree-lined streets and lush landscapes makes Wethersfield one of the most beautiful towns in Connecticut—and the rural retreat. But there’s more to this beauty than meets the eye; the small hamlet also has a storied past, evident in everything from its plethora of architectural wonders to its many historical heritage sites,

  • Things To Do: The Broad Street Green; Wethersfield Heritage Walk; Heritage Way Bike Route; Heirloom Market; Old Wethersfield Historic District
  • Wine & Dine: The Charles; Lenoci’s Italian Kitchen; Kaliubon Ramen
  • Stay The Night: Silas W. Robbins House; Goodwin Hotel (10 minutes)

6 Greenwich

The First Presbyterian Church is located in the heart of Greenwich.
Via: Shandley McMurray
The First Presbyterian Church is located in the heart of Greenwich.

Though just a short train ride from NYC, the cozy Connecticut town of Greenwich is all small-town charm: from its historic buildings to its Main Street USA vibes. But Greenwich’s location near the Big Apple also gives it a somewhat metropolitan flair seen throughout its distinctive local shops, boutiques, and eateries.

  • Things To Do: Greenwich Avenue and Historic District; Greenwich Point Park; Putnam Cottage Tour; Babcock Preserve; The Flinn Gallery
  • Wine & Dine: Le Fat Poodle; L’escale Restaurant & Bar; Elm Street Oyster House
  • Stay The Night: Delamar Greenwich Harbor; The J House Greenwich

RELATED: This Quirky Connecticut Book Barn Might Be The Place For Book Lovers

5 Cornwall

Crab apple trees and blossoms
Depositphotos
Cornwall, Connecticut USA Crab apple trees and blossoms.

With a location at the foothills of the Berkshires and housing much of Mohawk State Forest, it’s no surprise that Cornwall is famed for its scenic natural setting. And this forested beauty is not just easy on the eyes, it’s an epic outdoor playground, too—complete with plenty of year-round recreation opportunities for everything from biking to skiing.

  • Things To Do: Mohawk Mountain Ski Area; Mohawk State Forest; West Cornwall Covered Bridge; Housatonic Meadows State Park; Bike the Western New England Greenway
  • Wine & Dine: frank.food company; The Village Restaurant (10 minutes); When Pigs Fly South Southern BBQ (15 minutes)
  • Stay The Night: Cornwall Inn; Winvian Farm (20 minutes)

4 Old Saybrook

Old Saybrook, Connecticut, USA
Photo by Matt Hatfield on Unsplash
Old Saybrook, Connecticut, USA

Quintessential New England waterfront vibes abound in the pleasantly idyllic Old Saybrook. Think all the frills of a harbor town, like timeless charm, scenic seaside beauty, and locally-owned storefronts that make this welcoming community perfect for a day away—or a long (relaxing)weekend stay.

  • Things To Do: Harvey’s Beach; Fort Saybrook Monument Park; Visit Essex Village; The Katharine Hepburn Cultural Arts Center; Rocky Neck State Park
  • Wine & Dine: Alforno Trattoria; Little Pub Old Saybrook; The Essex
  • Stay The Night: Water’s Edge Resort & Spa; Saybrook Point Resort & Marina

RELATED: It's Rumored That Captain Kidd's Famous Treasure Can Be Found On This Connecticut Island

3 Branford

Branford Town Green, Connecticut
Wikimedia Commons
Branford Town Green, Connecticut

Though the bustling CT town of New Haven is right on its doorstep, the picturesque and pretty Branford has a distinctly charming small-town feel that can be seen everywhere, from its bucolic beaches to its stately homes. From basking in beachy vibes to trekking the town’s scenic trail, this lovely suburb has it all.

  • Things To Do: Branford Trail; Cruise to Thimble Islands; Shore Line Trolley Museum; Branford Point Beach; Stony Creek Brewery; Branford Supply Pond Park
  • Wine & Dine: Home; Rosso Vino; Mosaico Cuisine
  • Stay The Night: Owenago Inn; Thimble Islands Bed & Breakfast

2 Mystic

Boats cruising up the Mystic River in southeast Connecticut toward The Mystic Seaport
Photo by Rusty Watson on Unsplash
Boats cruising up the Mystic River in southeast Connecticut toward The Mystic Seaport

Tourists will be hard-pressed to find a more charming Connecticut town than Mystic. Its rich maritime heritage is evident at every street corner, from the numerous sea-related museums that dot the town to the different annual events honoring boats and pirates. Whether looking to stay on dry land or venture out at sea, there are endless fun things to do in Mystic.

  • Things To Do: The Seaport Museum, Olde Mystic Village, The Mystic Aquarium, Historic Ship Nautilus & Submarine Force Museum, Mystic Downtown Marina, Mystic Museum of Art
  • Wine & Dine: Mystic Pizza, Trattoria Amalfi, The Mariner
  • Spend The Night: Hilton Mystic, Steamboat Inn, Taber Inn And Suites

1 Colebrook

Colebrook River Lake Dam
Depositphotos

The landmark Colebrook River Lake Dam in Connecticut during a new england winter.

A sweet escape from the rigors of daily urban life, this sleepy town in the Connecticut countryside offers a therapeutic dose of natural beauty and small-town charm. Surrounded by sprawling hills and sparkling waters, Colebrook is the perfect playground for nature lovers and comes to its own during fall when hues of yellow, red, and orange highlight its lushly forested spaces.

  • Things To Do: Lake Triangle Dam, Algonquin State Forest, Colebrook River Lake, Peoples State Forest
  • Wine & Dine: Barnstormer's Burgers & More, Colebrook Store
  • Spend The Night: Days Inn by Wyndham Torrington, Royal Coachman Tavern