New England has no shortage of cute and charming places to visit (especially during fall)! These are some of the best small towns in Connecticut to add to your bucket list!
We have covered several Connecticut small towns ranging from the seaside communities to inland villages and there are plenty more than just these ones on the guide!
You will also find many of these CT towns are easy day trips from Boston, Hartford, and other larger places (even NYC!)
If we missed any charming small towns or cities in Connecticut, let us know in the comments. Thanks!
Best Small Towns in Connecticut
Niantic
A gem of a village in Long Island Sound, Niantic has been around since before the 1600s.
When in this scenic town, hit the Niantic Bay Boardwalk, the Rocky Neck State Park, and McCook Point Beach for harbor views.
If you’re a bookworm, check out the Book Barn. Three Belles Outfitters is the go-to spot for water sports fans. Speaking of water, you can catch Striper Snax and Black Hawk in the waters here.
Accommodation-wise, we recommend the Harbor Hill Marina inn, which has great food and views.
Putnam
With a population of less than 10,000, Putnam is an ideal spot to relax.
This New England small town offers sights like the Gertrude Chandler Warner Boxcar Children’s Museum, the Bradley Playhouse, and the Complex Performing and Creative Arts Center.
The Historic Downtown district is popular with art enthusiasts, while outdoor fans can enjoy hiking, cycling, swimming, or simply gazing at the Quinebaug River from Putnam River Trail.
Make sure you also check for any events or exhibitions, as Putnam is full of them!
Colebrook
Looking for a quiet getaway that also comes with beautiful scenery and a sense of history?
Colebrook is home to the Rock Hall 1900s Tudor revival house. There are also beautiful views from sights such as the Gaylord Pond and Lake Triangle dams.
Visit the Haystack Mountain Observation Tower to gaze at the Long Island Sound marine sound and tidal estuary. You can hike up the trail in the state park.
Colebrook is known for the 4th of July celebrations. Visit the Colebrook House for food, and Rock Hall Luxe for lodging.
Westport
Westport is conveniently close to NYC, which means it can be a perfect escape for a weekend!
If you’re a fan of art, the Westport Country Playhouse and the Museum of History and Culture are great places to visit in this quiet town.
It is also beaming with great eateries and shopping locations in its downtown area, which runs along the Saugatuck River.
The outdoor Levitt Pavilion hosts live music shows during the summer season.
The Rolnick Observatory, Burying Hill Beach, and Sherwood Island State Park are also great to visit.
Greenwich
Greenwich is one of the richest small towns in CT, as well as one of the oldest.
A short train ride away from NYC, it includes a number of historical buildings such as Bush-Holley, Thomas Lyon, and the Putnam Cottage.
Explore the town further by checking out Greenwich Avenue, Bruce Museum, and the Finn Gallery. Architect enthusiasts should definitely visit the Philip Johnson Glass House.
Fans of nature should not miss the Audubon Center. All restaurants and boutiques here are world-class. The town also hosts the Greenwich International Film Festival.
West Cornwall
West Cornwall is most known for Cornwall Bridge built in 1762, which you might have seen a lot on social media.
This village is at its peak scenic beauty in fall, while outdoor activities like kayaking, fishing, camping, and canoeing reel in quite the crowd in the summer, including the local population.
You can find a lot of souvenir shops and eateries when in the village to get the real taste of New England cuisines.
Bethel
Full of beautiful sycamore trees, Bethel is more than meets the eye.
Home to the headquarters of Duracell and the Greenwood Avenue Historic District, this small town is full of antique stores, local eateries, and farms.
Bethel’s indie movie theater also hosts the annual Connecticut Film Festival.
Other notable locations are the public library and Blue Jay Orchards. Monster Mini Golf and Laser Tag, Sky Zone, and the Toy Room are all great for children.
Madison
A popular attraction in Madison is Hammonasset Beach State Park, the biggest beach in Connecticut (and one of the best beaches in New England). Meigs Point Nature Center and the Shoreline Greenway Trail are also hit with outdoor fans.
The town’s beautiful New England-style buildings include galleries, music venues, and cafes which often exhibit art from local artists.
The Madison Arts Barn and Madison Art Cinemas host great events throughout the year, so make sure to catch some!
New Milford
Located in western Connecticut and lying on the riverbanks of the Housatonic, New Milford is a quiet town dating back to indigenous times.
It is home to 12 landmarks listed in the National Register of Historic Places, including Boardman’s Bridge, New Milford Center Historic District, and the Housatonic Railroad Station.
If you’re more of an outdoor person, you can hike the New Milford River Trail.
Top-rated restaurants are the Sanzari’s New Bridge Inn and the B & W Bakery.
Litchfield
Welcome to Litchfield, a beautiful village that offers the ultimate New England experience.
Around since the mid-1700s, Litchfield is full of scenic locations such as the White Memorial Conservation Center and the Topsmead State Forest where you can also go for picnics.
The area itself is full of historic buildings, most of which are located in the Litchfield Historic District. The Historical Society and Museum cater to history enthusiasts while the local restaurants cater to your taste buds!
Milford
The coastal city of Milford almost feels like a painting. It is home to the famous Milford Oyster Festival, which takes place on the third Saturday of each year’s August.
You can also visit the Milford Cultural Center where you can attend different events.
This city is most known for its beaches, its state park, and the coastal center of Audubon. Most of the local cafes, shops, and eaters are revived historic buildings, adding an extra charm to Milford.
Cornwall
Named after the famed English county, Cornwall has been around since the early 1700s. If you ever wind up here, check out the Mohawk State Forest which has given this town the “Greenest Town in Connecticut” moniker.
Don’t miss the Cornwall Library with its massive collection of nearly 30,000 items.
The historic Cornwall Bridge, railroad station, and West Cornwall Covered Bridge are notable areas to visit, as is the deconstructionist architectural marvel, House VI.
Essex
The sense of history in Essex is breathtaking. There’s a ton to see in this beautiful town: the famous Savings Bank, Centerbrook Congregational Church, Hill’s Academy, and the Essex Art Association Gallery to name a few.
It is most known for the still-functional Essex Steam and Essex Clipper Dinner trains. If you plan your trip just right, you can even catch Thomas the Tank Engine which is a big hit with children.
For accommodation, definitely go for the Copper Beech and the Griswold inns.
Monroe
Named after the 5th U.S. president. Monroe is a quiet town full of curiosities.
Comprising 9 neighborhoods, it is home to a number of historic buildings such as the Stevenson Dam Hydroelectric Plant, the Daniel Basse and Thomas Hawley houses, as well as the Monroe Center Historic District.
If you’re a fan of horror, then rejoice! The famous Warren Occult Museum and Stepney Cemetery are located in Monroe. Ironically, so are 11 houses of worship that you can visit.
Chester
Incorporated in 1836, Chester echoes the industrial era of Connecticut. Here you can find the historic Chester-Hadlyme Ferry, as well as the Beth Shalom Rodfe Zedek synagogue, one of Chester’s architectural marvels.
Despite having an industrial background, the town is surrounded by scenic nature which you can enjoy from locations such as Camp Hazen YMCA and Villa Bella Vista.
Most of the town’s historic buildings are now galleries and restaurants, offering great service and food.
Kent
With breathtaking sights to take in at Macedonia Brook and Kent Falls State Parks, Kent is the ultimate town to relax in.
The hiking trails will present you with vistas of Appalachia. the Catskill and Taconic Mountains, as well as 17 waterfalls. If you are an art fan, you can visit the Sloane-Stanley Museum.
Make sure to check out the Bulls Bridge, and the inn of the same name which offers delicious local cuisine! Another recommended eatery is the Ore Hill & Swyft.
Mystic
Named after the Pequot term “missi-tuk,” Mystic is a former seaport most known for its three historic districts, many of which include notable landmarks.
If you’re into maritime history, Mystic is the place to be: the massive Seaport Museum, the Charles W. Morgan whaling ship, the Historic Ship Nautilus, and Submarine Force Museum…take your pick!
Mystic is also well-known for the movie Mystic Pizza, and guess what?
You can taste the pizza at the restaurant in the Submarine Museum! We also recommend the Olde Mistick Village mall.
Columbia
Welcome to Columbia, Connecticut! When you arrive in this beautiful town, make sure to stroll down the Columbia Green Historic District to see the many historic buildings there, including the Town Hall, the Congregational Church, and a WW1 memorial. Hiking fans will enjoy the Hop River and Airline trails.
For loop, trails check the Mono Pond Recreation Area. Hit Trailside Treasure for antiques, and the Main Moose for some great food. There is more to Columbia than meets the eye!
Washington
No, it’s not the one from DC! Washington CT not only has beautiful scenery but is also home to a number of historic buildings and attractions.
A must-visit is the Hidden Valley Preserve which includes a bridge named after the famous writer Thoreau, the perfect location for photography!
Hike through the wooded areas, and end up at the Steep Rock Reservation and Gunn Historical Museum for an extra sense of culture and history. The Hollister House is also a popular spot!
Chaplin
Chaplin may be small, but that’s exactly why it’s a great location to visit and is one of the best small towns in Connecticut.
This little CT town includes interesting locations such as the Chaplin Museum, the Witter House, and a famous pool on the Natchaug River.
Be sure to pass by the Chaplin Historic District which includes beautiful wood-frame houses and the Congregational Church building in the early 1800s.
The old town hall, library building, and the historic Eaton’s Store are also popular!
Old Saybrook
What do you get if you mix Katherine Hepburn and one of the oldest towns in Connecticut? Old Saybrook! Many claims that this is one of the most beautiful towns in CT, and they’re not wrong.
You can visit Hepburn’s mansion, her eponymous Arts Center, Florence Griswold House, as well as the various galleries.
Hike to the Lynde Point Lighthouse, as well as the Rock Neck State Park. If you like beaches, hit Harvey’s Beach. Local eateries here offer great seafood, so grab a bite for sure!
This is not only one of the most charming towns in Connecticut, but the US as well!
Guilford
Located in New Haven County, Guilford is a charming town located on the CT seacoast. There are plenty of places to visit here, such as the five historic house-museums which date back to the 1600s.
The Henry Whitfield House is the oldest one in the entire Connecticut area. Outdoor landmarks include the Metacomet Ridge, Bluff Head peak, and Mattabesett and Westwoods trails.
Also pass by the Bishop’s Orchards for wine, apples, and pumpkins! Guilford is also full of parks where you can have picnics!
Weston
Housing the biggest portion of Devil’s Den Preserve, Weston is the closest Connecticut town to NYC.
Most of the activity here is focused on the Town Center, but there are also three historic districts that you should definitely visit: Bradley Edge Tool Company, Kettle Creek, and Norfield.
In these districts, you can find everything from churches, 18th and 19th-century buildings, and historic houses. There are also 7 parks and open spaces which you can pass by if you prefer the outdoors.
Did we miss any of the best small towns in Connecticut? Let us know your favorite Connecticut small towns below!
More New England Travel Guides
- Day trips from Boston
- New Englandʻs best beaches
- State parks in New England
- Best small towns in Maine
Pin this Connecticut Small Towns Guide
Megan is a travel blogger and writer with a background in digital marketing. Originally from Richmond, VA, she now splits her time between Frankfurt, Germany and Arctic Finland after also living in Norway, Armenia, and Kazakhstan. She has a passion for winter travel, as well as the Nordic countries, but you can also find her eating her way through Italy, perusing perfume stores in Paris, or taking road trips through the USA. Megan has written for or been featured by National Geographic, Forbes, Lonely Planet, the New York Times, and more. She co-authored Fodor’s Travel ‘Essential Norway’ and has visited 45 US states and 100+ countries.
What about Woodbury? We never get mentioned. We have beautiful homes, great restaurants and beautiful scenery. There is also a lot of history here. We’re also the antique capital of CT!
Housing the biggest portion of Devil’s Den Preserve, Weston is the closest Connecticut town to NYC.
Where did you get this from? Greenwich is the closest town to NYC Westonis approximately 30 minutes farther east, with six or seven towns in between it and the NYS border. BTW, you list Greenwich in this article about small towns. If I’m correct there are about 70,000 people in the town, which makes it far from small. Also Mildord has almost 60,000 which should exclude it from this list.
Your list is too big and has too many not small towns, but any publicity good publicity.