15 Most Beautiful Small Towns in Connecticut
It’s often said that time slows down in small towns. While big cities move at breakneck speed, people in smaller communities tend to take more time with their day-to-day lives. This is a wonderful thing for those who lead hectic lifestyles, but it also has its drawbacks. Connecticut has some of the most beautiful small towns and their proximity to New York City make them a great and beautiful getaway.
My family and I have lived in Connecticut for over 20 years and are constantly finding fun new towns to visit. Wether you live in NYC, Boston or somewhere else in New England you will love these little towns too!
In this blog post we’ll explore 15 beautiful small towns in Connecticut that offer everything from scenic views to historical charm they can only be dubbed the most beautiful small towns in Connecticut.
Essex, Connecticut
Essex is the perfect small town for anyone who wants to experience a little bit of everything. From beautiful historic homes to quaint shops and restaurants, it’s sure to please everyone in your group!
Essex was created in 1741 and was once a thriving port town. Today, some of the buildings you can see in Essex are over 200 years old! Stroll down Maine Street and see these old homes and do some window shopping. Stop for a bite to eat at the Griswold Inn or head to the Essex Steam Train for a scenic ride.
Essex is so beautiful at Christmas time, the Steam Train runs a Polar Express themed ride and the entire downtown is a winter wonderland with white lights and greenery.
Stay in the beautiful Griswold Inn in Essex, CT
This charming inn has large and spacious rooms and has been lovingly restored to its former glory while still maintaining its old world charm.
Click here for booking information.
Chester, CT
Chester was originally founded in 1692 and today it has over 2000 residents that keep this peaceful Connecticut town running! Chester is home to some beautiful historic homes. Built on the Connecticut River, this town has more charming vistas than any other town on this list.
Plus it has a real life castle! Gillette’s Castle was built by William Gillette, who was an actor well known for playing Sherlock Holmes. He fancied himself a real life inventor and detective and built himself a castle that is befitting of Sherlock Holmes himself.
While you are there you can visit the suprisingly interesting Chester museum. Or visit art galleries that dot Main street.
Plus you can take a ferry to Chester to see the beautiful fall foliage in the autumn. You will be amazed at how spectacular it is.
Cornwall, CT
Cornwall, CT is a beautiful town on the Housatonic River.
Cornwall is one of Connecticut’s oldest towns, making it a popular destination for history buffs! The beautiful Housatonic river runs through the town. You can go fishing with Housatonic River Outfitters. Or just enjoy the banks of the river while exploring the West Cornwall covered bridge. Cornwall is the most beautiful when you get out in nature and there are tons of great hikes!
There are tons of restaurants here too so your family won’t go hungry during their search for these most beautiful small towns in Connecticut!
Madison, Connecticut
Madison, CT is another one of Connecticut’s most stunning small towns.
Madison is about a half hour drive from New Haven and it is worth the trip! In Madison you can visit their beautiful historic homes, visit Hammonasett State Park, Beach or peruse the independent bookstore RJ Julia.
It doesn’t matter what time of year you come because Madison always looks its best.
Stay at the Madison Beach Hotel in Madison
Overlooking Long Island Sound the Madison Beach Hotel is a perfect place to stay when visiting Madison, CT. Operated by the Hilton, this luxury hotel is perfect for a romantic evening or a night on the town.
Click here for booking information.
Kent, Connecticut
Kent, CT is one of the most beautiful places in Connecticut in the autumn.
The town of Kent is about a half hour drive from Hartford and is home to Connecticut’s highest waterfall at Kent Falls State Park. Speaking of Kent Falls, it has been voted year after year as the most beautiful fall foliage in New England.
This small, scenic town has changed little since the late 1800s when most people practiced agriculture to support their families! If you’re looking for an escape during any time of year, take a trip down to beautiful Kent.
Lebanon, Connecticut
Lebanon, CT is also one of Connecticut’s hidden treasures that you need to visit if you haven’t already been there yet. Lebanon sits near the border with Rhode Island so coming here makes for the perfect day-trip from Boston or Providence where many tourists travel to every year! The old buildings in Lebanon date back as far as 1730 which gives visitors lots of historic charm and character.
If you love a Renaissance Festival there is a great one every fall in Lebanon. Bring the whole family to watch magic shows, sword swallowers, eat a giant turkey leg, and watch falconers.
Washington, Connecticut
Washington, CT is another small town in Connecticut that’s well known for its beautiful views of the Housatonic River. It’s a quaint and charming little village with old buildings, antique shops, art galleries, restaurants and more! Washington has some great places to hike and explore the outdoors as well.
If you love “Gilmore Girls” you will love visiting Washington. This town was the inspiration for Stars Hollow.
Stay in the hotel that influenced “Gilmore Girls!”
The Mayflower Inn and Spa is just about the most beautiful inn I have ever seen! It is expensive but one of the most spectacular stays you will ever have. Perfect for a honeymoon or anniversary trip.
Click here for booking information
Litchfield, Connecticut
Litchfield Connecticut is a charming small town and is great for a day trip of a weekend.
Start at Mount Tom State Park and stretch your legs while seeing some of the most beautiful views in Connecticut. Or head to Whites Memorial Conservation Center to walk around Lake Bantam.
Enjoy all the charming shops that surround Litchfield’s green and grab dinner at one of many highly rated restaurants downtown.
Stay in the Litchfield, Inn
The Litchfield Inn is a great place to spend the weekend. Nestled in the Litchfield countryside, this Inn is a great deal for a spectacular stay. The breakfast is highly rated and the grounds are beautifully maintained.
Click here for booking information.
Ridgefield, CT
Ridgefield, CT is small town life at its most beautiful. It’s the perfect place to take a walk, have a picnic with friends or enjoy some time at one of the many parks around town. There are also plenty of shops and restaurants for those who like shopping or dining out as well!
Stay at the West Lane Inn
The West Lane Inn is an old farmhouse that has been converted to a small inn. The inn is close to shops and great restaurants and has air conditioning in each room.
Click here for booking information.
Wilton, CT
Wilton, CT is another small town that’s not too big but has plenty to offer visitors. You can spend your day outdoors by visiting nearby hiking trails – there are more than 30 miles worth so it will be easy to get lost in nature if thats what you’re looking for. Wilton doesn’t give up when it comes to entertainment either: they host their own little league tournament every year where locals battle it out to see who can win.
Visit Weir Farm National Historic Park to learn about the impressionist painter J. Alden Weir.
Greenwich, CT
Greenwich, CT offers a little more than other Connecticut towns. Located just outside of New York City, this town has plenty to offer visitors including great shopping opportunities in the downtown area as well as many restaurants and cafes for those who like dining out or want to enjoy some time strolling around.
Visit the Greenwich Historical Society and learn about the early settlers of Connecticut and enjoy their park like grounds and cafe.
Stay at the Delamar Greenwich Harbor Hotel
If you want to enjoy luxury overlooking the ocean then the Delamar is the place to stay! Beautifully appointed and absolute perfection in every guest room. Walking distance from Main Street and tons of shopping.
Click here for booking information.
Mystic, Connecticut
Mystic, CT is a place that might be the perfect getaway for anyone who likes to spend time outdoors. The town is on the coast and has beaches, parks, trails as well as plenty of opportunities to enjoy nature in general – there are even several places you can go boating if thats what floats your boat.
There is also a great aquarium for little ones and a living history seaport.
Stay at the Whaler’s Inn in Mystic
The Whaler’s Inn is in the charming downtown of Mystic. Within walking distance of Mystic Seaport and delicious Mystic Pizza you will be charmed by this hotel.
Click here for booking information.
Old Saybrook, Connecticut
Old Saybrook, CT has a small but beautiful main street area where you can go shopping or enjoy the many cafes and restaurants in town. There are also plenty of beaches nearby if thats what your’e looking for, as well as a great 18-hole golf course to try out when its time to get some exercise.
Plus there are beautiful old homes and lovely walking trails.
Stay at Saybrook Point Resort
This seaside resort has 2 large salt water pools so you can swim year round. Ocean views are available in Queen and King bed rooms. Highly rated restaurant called Fresh Salt will be a great place to dine on the patio.
Click here for booking information.
Bethel, Connecticut
Bethel, CT has an historic past that dates back centuries, with the first settlers arriving in 1650. The town has a lot of historic sites for visitors to visit and other historical homes and buildings on Main Street dating as far back as the 1700s that are still standing today!
Bethel also offers plenty of outdoor activities like hiking trails, mountain biking paths, sailing lessons and more so you can explore all that it has to offer or just take some time out from your day to enjoy its natural beauty.
There may not be a ton of nightlife options but there are plenty of coffee shops or the kids favorite ice cream spot called Cream and Sugar which makes enormous milkshakes.
Farmington, Connecticut
Farmington, CT is a town that is just west of Hartford, CT and has many historic sites – as well as plenty of food options.
Farmington’s downtown area features old buildings with traditional architecture and New England rock walls.
Farmington also offers some fun activities like rock climbing at Rattlesnake Mountain, hiking or biking in various parks/trails around the outskirts of the city or enjoying one of Connecticut’s best-kept secrets: The Stanley-Whitman House. This house offers tours by costumed docents and gives you a look back at life during Colonial Connecticut.
If you love shopping there is one of the largest shopping malls in Connecticut called the Farmington Mall, so you can engage in some retain therapy as well.
This state is full of amazing small towns that are worth visiting so don’t feel limited by our list if these aren’t your favorites. There’s something here for everyone with each town having its own special charm and personality!
If you want an idea of things to do in Connecticut while you are visiting this small town please visit
The Ultimate Guide to Connecticut.
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