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18 Top-Rated Small Towns in Connecticut

Written by Alison Abbott and Shandley McMurray
Updated May 26, 2022

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While it may be the third smallest state, Connecticut packs a ton of natural beauty and adorable small towns within its captivating borders. From sparkling lakes to crashing waterfalls to sandy beaches to verdant forests, a visit to the Nutmeg State will fill your lungs with fresh air and your heart with joy.

Feel your shoulders relax as you wind your way through tree-lined streets leading from one small town to the next, ogling nature's gifts, which are made even more magnificent with a kaleidoscope of fall's brightest colors.

Soak up the maritime feel of tiny coastal towns, stop in for a treat at a mom and pop restaurant, shop in a local boutique, or kayak down the river of a quaint, historic village. Traditions from New England and sophistication from New York combine for an interesting assortment of small towns with all the modern conveniences a visitor could need.

Plan your travels with our list of the best small towns in Connecticut.

1. Mystic

Lobster traps on the dock, Mystic, Connecticut
Lobster traps on the dock, Mystic, Connecticut

There are few small towns in Connecticut as charming as Mystic. Established in 1684, Mystic's maritime history is evident at every turn in this former shipbuilding seaport. Throughout the year, annual events celebrate boats, pirates, schooners, and more. With over a dozen ways to get out on the water, every type of adventurer will find his or her groove.

The Seaport Museum is worthy of at least a few hours of your time. It's packed with interesting things to see – like a recreated 19th-century fishing village, children's museum, and an old wooden whaling ship. You can also board a cruise from here.

Mystic Seaport
Mystic Seaport | Photo Copyright: Shandley McMurray

The Mystic Aquarium is another must-see, with beluga whales, seals, and a bevy of other creatures (hello, penguins) who will wave a fin at your kids in greeting. Across the street lies the lovely Olde Mistick VIllage, an open-air mall set in a recreated 18th-century village. Come hungry as there are a ton of eateries to choose from. Don't miss the flavored popcorn or fresh fudge on offer.

Board the world's first nuclear-powered submarine at the Historic Ship Nautilus & Submarine Force Museum. Parents will appreciate the free admission, and kids will love the working periscopes. Finally, make sure to have a slice at the restaurant Julia Roberts made famous in Mystic Pizza.

Accommodation: Where to Stay in Mystic

Read More: Top-Rated Things to Do in Mystic, CT

2. Chester

Fall foliage along the Connecticut River, Chester
Fall foliage along the Connecticut River, Chester

Chester's industrial roots in shipbuilding and milling are still evident in the downtown area. The town places a high priority on preserving its historical heritage, and many antique houses and buildings have been thoughtfully preserved for future generations. A strong cultural scene often goes hand in hand with historical priorities, and Chester's budding arts scene is no exception.

Numerous galleries, boutiques, and theater add another layer of interest for visitors to this adorable small town. The surrounding topography, in addition to being scenic, provides great hiking and walking areas accessible directly from town. Chester is the perfect destination for a romantic getaway.

Visiting nearby Gillette Castle State Park is one of the best things to do in Connecticut. Hop on the Chester-Hadlyme ferry to cross the river to this interesting attraction.

Accommodation: Where to Stay in Chester

3. Greenwich

Greenwich Ave
Greenwich Ave | Photo Copyright: Shandley McMurray

Located on Connecticut's Gold Coast, Greenwich is a financial powerhouse and also an exciting place to visit. As one of the Nutmeg state's oldest towns, it also represents one of the richest.

Less than an hour train ride from New York City, Greenwich gives the feel of a small town with all the amenities of the big city. Restaurants are world-class, as is the shopping. You'll find the usual high-end brands, but also a hip selection of one-of-a-kind boutiques and galleries. This has helped it to become one of the top weekend getaway destinations in Connecticut.

Aerial shot of Greenwich
Aerial shot of Greenwich

For the nature-lover, be sure to stop at the Audubon Center. This 300-acre sanctuary will have you feeling like you are a world away. You can also walk the town exploring the bustling Greenwich Avenue or visit attractions like the Flinn Gallery or Bruce Museum, an eclectic place where artifacts and exhibits are carefully curated for every visitor. The Philip Johnson Glass House is an architect lover's dream.

Accommodation: Where to Stay in Greenwich

Read More: Top-Rated Attractions & Things to Do in Greenwich, CT

4. Colebrook

Lake Triangle, Colebrook
Lake Triangle, Colebrook

This sleepy town nestled in the Connecticut countryside is perfect for a restful and relaxing weekend. Located north of Hartford, it's oozing with rural, small-town charm. The area's hilly location makes it particularly stunning in the fall, when the countryside lights up with shades of red, yellow, and orange fall foliage. Check out the views at the Gaylord Pond Dam or Lake Triangle Dam.

For an amazing scenic panorama of Long Island Sound and the tri-state area, head to the Haystack Mountain Observation Tower. The state park with the same name provides trails and a rugged path to the top.

5. Kent

Waterfall near Kent
Waterfall near Kent | Photo Copyright: Shandley McMurray

Kent is a quiet respite in the busy tri-state area. Although the population of this small town is less than 3,000, it offers panoramic views with its ruggedly beautiful landscape. It's a great place to visit year-round, but in fall, this area lights up with vibrant colors as the leaves begin to turn.

Take advantage of all the natural beauty of Kent at Kent Falls State Park, where you can explore one of the state's best waterfalls, covered bridges, and miles of trails. It is deemed one of the best State Parks in Connecticut. Once you've seen its vast beauty up close, you'll understand why.

You can also get unparalleled views at the Western New England Greenway or East Kent Hamlet Land Trust. Learn more about the history of this area at the Kent Historical Society or Kent Furnace.

The picturesque Eric Sloane Museum is another must-see that houses the artist's works, his studio, and a collection of his hand tools.

6. Westport

Saugatuck River and Westport
Saugatuck River and Westport | Photo Copyright: Shandley McMurray

Scenic Westport is located just 50 miles outside of New York City on a prime piece of waterfront real estate known as Connecticut's Gold Coast. The vibrant downtown area along the Saugatuck river has world-class shopping and top-notch restaurants, as well as a newly renovated library and the outdoor, Levitt Pavilion, which boasts free (and some paid) concerts in the summer. Main Street is about as quaint and small town as it gets, yet it's graced by big names like Lululemon, Tiffany's, and J.Crew.

MOCA Westport is the town's impressive contemporary art museum that can rival any NYC-based venue. It boasts programing in both the visual and performing arts. You won't want to miss a play at the Westport Country Playhouse, where the stage has been graced by the likes of Paul Newman, James Earl Jones, Robert Redford, and Eartha Kitt.

View across the Saugatuck River in Westport
View across the Saugatuck River in Westport

Active travelers will find a multitude of water sports to indulge in, especially if they plan on spending time at the pristine Compo Beach. Sailing, kayaking, stand up paddleboarding, windsurfing, and fishing are all part of the athletic scene. Old Mill Beach and Sherwood Island are also popular spots to lounge on the sand.

For a scenic late afternoon stroll, find the river walk (part of which runs around the library's peninsula) and time it to watch the sun set over the sparkling water.

Westport and the surrounding area is part of the Connecticut Antiques Trail, which snakes its way through scenic small towns of the area.

Accommodation: Where to Stay in Westport

Read More: Top-Rated Things to Do in Westport, CT

7. New Canaan

Glass House, New Canaan
Glass House, New Canaan | Photo Copyright: Shandley McMurray

New Canaan is a charming town located in Fairfield County, a quick 20-minute drive from Stamford or an hour from New York City. Another commuter haven, New Canaan boasts a large downtown core that's so sweet, you'll forget it's bigger than the short Main Street you'll find in other small towns on this list.

Elm Street is where you'll find most of the upscale shops, cafés, and restaurants. This is a very affluent town, so expect the prices to reflect the clientele. There are plenty of ice-cream stores to keep kids happy.

The most highly rated attraction in New Canaan is the famous Glass House. One of the most interesting homes you'll see, and one of the best places to visit in Connecticut, this eclectic spot was designed and lived in by architect Philip Johnson. It is mesmerizing, and so unique you'll talk about it for years to come. It is only open between mid-April and mid-November, so plan accordingly.

The Silvermine Arts Center is worthy of a visit, especially to wander around the neighborhood of the same name. Akin to walking through a postcard, this picture-perfect section of town is delightful. Babbling brooks, historic homes, white picket fences, and waterfalls–this area really has it all.

The Inn at GrayBarns is one of the most popular places to stay in the area. It's gorgeous, intimate, and home to a tavern that serves up tasty dishes to hungry customers.

8. Fairfield

Town green in Fairfield
Town green in Fairfield | Photo Copyright: Shandley McMurray

An enticing small town lies serenely on Connecticut's Gold Coast. Named Fairfield, this lovely spot overflows with all the things you'd want for a perfect weekend getaway: boatloads of charm; top-notch restaurants; and five soft, sandy beaches.

Between Jennings, Penfield, South Pine Creek, Southport, and Sasco beaches, you're sure to find the perfect spot to lay your towel, take a dip in the Long Island Sound, or enjoy a picnic.

One of the best beach towns in the state, Fairfield lies between Bridgeport and Stamford, welcoming visitors who like to spend time soaking up the fun in the outdoor Fairfield Farmer's Market, history at the Fairfield Museum and History Center, and charm in the Old Post Road Historic District.

The Connecticut Audubon Society Birdcraft Museum and Sanctuary is peppered with wooden walkways and, of course, plenty of interesting birds on display.

If you've brought a four-legged friend along for the journey, don't miss a visit to Lake Mohegan Recreational Area. It's one of the best places to walk a dog in Fairfield County and boasts a cute beach, perfect for families in the warmer months.

Accommodation: Where to Stay in Fairfield

Read More: Top-Rated Things to Do in Fairfield, CT

9. Ridgefield

Prospector Theater in Ridgefield
Prospector Theater in Ridgefield | Photo Copyright: Shandley McMurray

Ridgefield is so alluring, you'll wish you could stay longer. It's set in the foothills of the Berkshire Mountains, and you can't beat the elysian feel. Stately homes line the streets, boutique shops sell their wares, and museums host interesting displays throughout this small town.

A visit to the Keeler Tavern Museum will take you back in time, but the nearby Aldrich Contemporary Art Museum, complete with a sculpture garden, will jump you right back to the 21st century.

The Prospector Theater is a cinema with heart. Run by a non-profit organization, this inspiring venture employs people with disabilities, giving them a chance to "sparkle, shine, and transform (their) passions into professions." They show everything from kids' films to classics to current Blockbusters.

The Ridgefield Playhouse is also good at entertaining its guests. This is where you can find everything from recitals to comedy shows to concerts.

Accommodation: Where to Stay in Ridgefield

Read More: Top-Rated Things to Do in Ridgefield, CT

10. Litchfield

The Village Green in Litchfield
The Village Green in Litchfield | Photo Copyright: Shandley McMurray

It's easy to fall in love with Litchfield, especially if you visit when the trees are alight in all their bright yellow, orange, and red glory. A sweet small town located about 50 minutes east of Hartford, this charming village is about as quintessentially New England as it gets in Connecticut.

American flags unfurl from historic buildings in this storybook town, which is dotted by white-spired churches, 18th-century homes, and white picket fences a plenty. Stop in for a bite at one of the local restaurants, but book a reservation if you're planning to visit on a summer or fall weekend.

Nature abounds at White Memorial Conservation Center and Topsmead State Forest, both of which are worthy of hours-long hikes and romantic picnics.

Accommodation: Where to Stay in Litchfield

Read More: Top-Rated Things to Do in Litchfield, CT

11. Essex

Houses along the Connecticut River in Essex
Houses along the Connecticut River in Essex

If you're a fan of The Gilmore Girls, you'll feel right at home in Essex. After all, the show's location, Stars Hollow, was based on this charming Connecticut town. Many of the historic buildings remain, and the surrounding area is filled with authentic farm structures dating back as far as the Revolutionary War.

Especially notable is the First Baptist Church of Essex. Built in the Egyptian Revival style, it is one of only three in the United States and one of the top attractions in Essex.

Visitors of all ages will enjoy a spin on the Essex Steam Train for an old-fashioned tour of several towns in the area. While you are soaking up the nostalgic feel of Essex, make sure to take advantage of the waterfront of this welcoming port. Both the Connecticut river and Long Island sound offer a plethora of water activities for adventure.

Accommodation: Where to Stay near Essex

12. Old Saybrook

Lynde Point Lighthouse, Old Saybrook
Lynde Point Lighthouse, Old Saybrook

Old Saybrook is one of Connecticut's oldest, and arguably most beautiful, towns. It's known to many as the once-home of actress, Katherine Hepburn. The Cultural Arts Center named after this Oscar-winning (dubbed "the Kate" by locals) legend is the area's top attraction.

Hepburn's former mansion sits overlooking Long Island Sound on a peninsula surrounded by other high-end real estate and the cutest private golf course visitors will ever lay eyes on. The area is great for a scenic walk out to the lighthouse, also known as Lynde Point.

Katharine Hepburn Cultural Arts Center in Old Saybrook
Katharine Hepburn Cultural Arts Center in Old Saybrook | Photo Copyright: Shandley McMurray

The historic Florence Griswold House has been turned into a museum that overlooks the sparkling Lieutenant River, behind it lies the modern, and inspiring, Robert and Nancy Krieble Gallery.

In town there are some great restaurants, several offering local seafood. Small shops feature vintage finds and antiques, many of which line the charming Main Street.

Get back to nature on a hike through Rocky Neck State Park. A treasured gem, you'll want to bring plenty of snacks and water along as this is a place worthy of hours of your time. Harvey's Beach is another visitor fave, well loved for its calm, shallow water and clean, soft sand.

Accommodation: Where to Stay in Old Saybrook

Read More: Top-Rated Things to Do in Old Saybrook, CT

13. Madison

Sunset by the sea at Madison
Sunset by the sea at Madison

Situated on the idyllic Long Island Sound, Madison is a seaside retreat. Take in panoramic views from one of the many outdoor spaces, like Hammonasset Beach State Park or Meigs Point Nature Center, or take a bike ride or stroll at The Shoreline Greenway Trail.

While the big draw of this area is its coastal beauty, there is still plenty to do if you aren't a nature-lover. Take a walk downtown and stop to browse through the unique shops, like the Audubon Shop or R.J. Julia Booksellers. Visitors can also take in a one-of-a-kind independent film at Madison Art Cinema.

14. Washington

Henry David Thoreau Bridge, Washington, CT
Henry David Thoreau Bridge, Washington, CT | Photo Copyright: Shandley McMurray

The rural town of Washington is known for not only its beauty but a host of historic architecture and cultural amenities as well. Close to New York City, its influence is evident in many of the attractions this area has to offer. You can visit the caves of Steep Rock Reservation or learn more about the Native American influence in the area at the Institute for American Indian Studies.

Head to the majestic Hidden Valley Preserve in Washington Depot to walk across the impressive Henry David Thoreau suspension bridge, a true marvel of engineering. The view from atop this bridge is worthy of at least a few photos. The bridge isn't too far from the parking lot, so don't worry if you're not a fan of hiking.

For those who don't mind a walk through the woods, this is a magnificent place bursting with beauty in the form of river views, babbling brooks, and towering trees.

If culture is what you crave, you can find it at the Gunn Historical Museum, preserving American artifacts and stories from the area, or the Washington Art Association and Gallery.

Before leaving Washington, don't forget to stop at Hollister House. Occupying 25 acres, this private garden is filled with whimsy, unique water features, and Japanese accents. It's well worth the visit.

For a relaxing stay you won't regret, book a room in the luxurious Mayflower Inn & Spa, an Auberge Resorts Collection. This retreat features plush amenities, five-star service, and captivating grounds. It also has a delectable restaurant you won't want to miss.

15. Milford

Beach houses in Milford
Beach houses in Milford

Tourists looking for an authentic Connecticut town by the shore should give Milford a try. Less crowded and touristy than many of the other beach towns in the southern region of the state, the charming character is hard to match.

Many historical buildings remain in the old town and have been repurposed into cafés, boutiques, and shops. The enticing town green is one of the largest in the state and a perfect spot to picnic or enjoy a book.

The beachfront offers rentals for enjoying the sand and surf, and Walnut Beach has one of the longest boardwalks in the state, which also offers disabled access. Silver Sands State Park is a popular 297-acre spot filled with dunes and marshes on the Sound.

Accommodation: Where to Stay in Milford

16. Niantic

Rocky Neck State Park
Rocky Neck State Park | Photo Copyright: Shandley McMurray

Also located on the Long Island Sound, Niantic is exactly what you would expect for a seaside village. Enjoy nature at Rocky Neck State Park or Niantic Bay Boardwalk, or take advantage of one of the many fishing adventures. There are quite a few from which to choose: Striper Snax or the Black Hawk can give you a full or half-day adventure on the deep sea.

If you are traveling with kids (or are a kid at heart) stop into the Children's Museum of Southeastern Connecticut, where you can beat the heat (or a rainy day) in their 5,000-square-foot facility geared towards interactive fun.

Niantic also has a selection of unique and funky shops. Visit The Book Barn, a bookstore boasting over 350,000 titles including rare and out of print books, or Three Belles Outfitters, the largest hobby kayak store on the east coast.

Accommodation: Where to Stay in Niantic

17. West Cornwall

West Cornwall Bridge
West Cornwall Bridge | Photo Copyright: Shandley McMurray

What Cornwall lacks in size, it more than makes up for with New England beauty, especially in the height of fall. Home to one of the few covered bridges in the state, this 1762 attraction is a must for the Instagram set. Visitors will also be smitten by the decorative gingerbread- house buildings, which seem to have stepped right out of a holiday setting.

The surrounding trees make the town especially picturesque during leaf-peeping season, but to avoid the crowds, visit this small town charmer during the other three. Located on the Housatonic River, visitors will find plenty of outdoor activity, including river rafting, fly fishing, canoeing, and hiking in Mohawk State Forest.

Accommodation: Where to Stay near West Cornwall

18. Putnam

The Courthouse, a top restaurant in Putnam
The Courthouse, a top restaurant in Putnam | Photo Copyright: Shandley McMurray

The banks of the Quinebaug River are home to the picturesque town of Putnam. Located in the northeast corner of the state, it represents a quintessential New England small town.

Centered around arts festivals, the downtown area offers an assortment of galleries, boutiques, and restaurants. Antique Malls are well represented in the town and have an impressive selection of vintage goods.

Putnam, along the Quinebaug River
Putnam, along the Quinebaug River

The Bradley Theatre is well known for the quality talent it attracts to its community program. The Gertrude Chandler Warner Boxcar Children's Museum is a great stop for families. Fans of the book series will find signed originals, children's activities, and artifacts all housed in an original boxcar.

More Related Articles on PlanetWare.com

imageThe Best of Connecticut: Begin your travels to this state with a read through our Top Tourist Attractions in Connecticut to find out where to go and what to see. If you are coming in summer, don't miss our article on the Best Beaches in Connecticut. Lastly, for a wonderful stay, have a read through our picks for the Top Resorts in Connecticut.

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