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5 Best Small Towns in Connecticut (2023)

Connecticut is the southernmost state in New England, and being close to big cities like New York and New Jersey, it is often referred to as the Tri-State area. The state is home to the renowned Yale University, along with many beautiful and historical tourist attractions. The state has beautifully preserved its colonial history in its small rural towns.

Connecticut has a lot to offer, much more than the Vineyard Vines and privileged prep schools. Nowhere else in the US will you find such beautiful little towns as you will find in Connecticut.

5 Best Small Towns in Connecticut

Here are some of the best small towns in Connecticut that you must check out.

1. Chaplin

Located in the heart of Windham County, the small town of Chaplin is named after one of its famous first settlers, Deacon Benjamin Chaplin. The main street of the town, known as Chaplin Street, is a designated Historic Place on the National Register of Historic Places. As you visit this quaint little town, it is a haven for book lovers as you get to curl up with a good book at their picturesque library, or you can explore the many trails around the town either on foot or horseback.

While you are at Chaplin, take a moment to stretch your legs and trek to the famous attraction known as Diana’s Pool, which is a stunning nature spot. Or indulge your taste buds at the Bach Dor Cafe, the perfect stop to gorge on some delicious fried food. If you want to check out how the town looked in a simpler time, you can opt to relax at the Passport Inn and Suites, one of the most renowned places to stay while in Chaplin.

2. Colebrook

Nestled in Litchfield County, the beautiful small town of Colebrook derives its name from Colebrook Country, England. This is a true blue New England town that is the ideal getaway for those who want to escape the hustle-bustle of big cities and daily life to get back in touch with the basics. Take the time to wander around this picturesque town, have a chat with the friendly locals, and make a stop at Rock Hall, a historic place on the National Register.

The best time to visit the town of Colebrook is during the 4th of July festivities, so plan your trip around that time. Also, check out the fantastic Colebrook Store to get your hands on some delicious local food that many call edible history.

3. Columbia

Columbia is a beautiful small town located in Tolland County. The city is named after the American ballad Hail, Columbia. The town’s Columbia Green Historic District is listed on the National Register of Historic Places, and it is one of the first places you should explore when you visit the town. Columbia is known for its rich history and heritage. The old stone buildings in the Columbia Greene Historic District date back to the early 19th century and are surrounded by charming greenery that will take you right back into the past.

This town is the ideal stop off the highway. Bordered by incredible nature walks and trees that stretch on for miles, Columbia boasts a unique train museum.

Any visitor to the town should definitely make a stop here during the summer months because the city provides passes to non-residents for summer activities. So grab your pass, rent a kayak, and get ready to have some fun. While in Columbia, indulge your sweet tooth with something tasty at Motta’s Pastry and bake Shop before continuing on your journey.

4. Chester

Located in the heart of the Connecticut River Valley, the beautiful town of Chester will surely win your heart. Whether you just drive into town through the dense forest region or you are cruising into town on the Chester/Hadlyme Ferry, you will be surprised and charmed the moment you lay eyes on the town.

This historic town was first settled in 1692, and there are many historic buildings that have been well preserved and give you the feel of exactly how an old city in New England would look like from that era. The peaceful atmosphere here and friendly locals make it a very relaxing place to visit.

There is much to do in the town, including exploring the history and culture of the town to indulging in some delicious local food. You will find many buildings to explore that are listed on the National Register of Historic Places, including the Old Town Hall of Chester. Private residences also showcase some of the most stunning architecture you will find in Connecticut.

As you wander around Main Street, you will find many quaint boutique shops, or you can dine at several award-winning restaurants. Many of the businesses here are running out of preserved 19th-century buildings.

The small town of Chester is popular for the arts. There are many art galleries around town that showcase numerous local talents. If you are lucky, you can even attend a live performance showing at the famous Norma Terris Theater.

5. Mystic

There are many beautiful small cities in Connecticut, but none as charming as Mystic. The town of Mystic was established in 1684. The town’s maritime history is famous and evident at every turn you take in this beautiful former shipbuilding seaport. Throughout the year, there are many annual events that celebrate boats, schooners, pirates, and more as a way to keep the history of the town alive. There are dozens of ways to get out on the water here, making it a perfect holiday for adventure lovers.

One of the top-most attractions you must check out in Mystic is the Seaport Museum, which takes up at least a few hours of your day. This museum is packed with many incredible things to see, including a recreated 19th-century fishing village, an old wooden whaling ship, and a separate children’s museum. You can even board a cruise from here.

Visitors to Mystic should also check out the Mystic Aquarium, which is home to beluga whales, seals, and a wide variety of other creatures, including penguins. Across the street from the aquarium lies the beautiful Olde Mistick Village, which is an open-air mall that is set up in a recreated 18th-century village style.

Another unique thing to do in Mystic is to climb aboard the world’s first nuclear-powered submarine housed at the Historic Ship Nautilus and Submarine Force Museum. This is a hugely popular place for families with children as admission is free. Children take an immediate liking to the working periscopes.

Once you are done exploring the town, make sure to stop to have a slice at the Mystic Pizza, made famous by Julia Roberts.

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