The Mystic Connecticut bridge spans the Mystic River, it carries foot traffic to the tourist district of town. Image credit Paul Latham via Shutterstock

9 Gorgeous Connecticut Towns To Visit In 2023

Connecticut perfectly blends suburbs, natural landscapes, and city living. Just across the Long Island Sound from New York City, Connecticut offers a much slower-paced vibe than its neighbor. It's home to some of the loveliest beach towns in New England, including Saybrook and Southport. Its vibrant history emphasizes all the state provides visitors by adding a deeper layer of meaning and backstory. Visit this fantastic state to better understand the nation's founding and explore the gorgeous tapestry of villages that makes this state so unique!

Old Saybrook

Beautiful Lynde Point Lighthouse, Old Saybrook, Connecticut
Gorgeous Lynde Point Lighthouse, Old Saybrook, Connecticut.

Established in 1854, Old Saybrook is one of Connecticut's oldest permanently settled areas. The European history of the location dates back some 200 years before its establishment, with Dutch arriving in the 1620s and English settlers arriving in 1635. Prior to European arrival, several native tribes, including the Algonquin, Pequots, and Nehantic, lived and thrived in the region for centuries. 

Old Saybrook is a gorgeous coastal community with many parks, historic sites, and a vibrant downtown center. Visit Ferry Point Marsh Wildlife Area to glimpse the town's diverse natural beauty. Or stop by the Preserve and Plum Bank Wildlife Area and explore the wooded marshlands filled with birds, fish, and much more. Drop by Penny Lane Pub near Old Saybrook Center for a diverse cuisine and decadent drinks. Their menu includes Belgian Waffles, fresh seafood, mimosa, and much more.


View from road one to Church Lane in beautiful spring day.
Church Lane on a beautiful spring day, Westport, Connecticut. Image credit Miro Vrlik Photography via

Westport is a community-centered township with plenty of natural splendor and a welcoming local population. The culture and history of this vibrant township are diverse, tracing their roots to native peoples, African-American ancestry, and several early European settlers. The Greens Farm is one of the oldest spots in town, with the five original Bankside Farmers establishing this site in the 1600s. You can still visit this breathtaking nature-rich site near the Connecticut coastline. Greens Farm is a must-see location for anyone who loves history, nature, and farm life. The Greens Farm Academy is a rustic structure and a fully functioning school. The campus is limited to the public.

Spend an afternoon exploring the nearby Sherwood Island State Park and Beach. Also, check out Seymour Rock and book a few nights at the Inn at Longshore for a luxurious stay!

New Canaan

Downtown street and clock in New Canaan, Connecticut.
Historic downtown in New Canaan, Connecticut. Image credit Miro Vrlik Photography via Shutterstock

Not far from Westport along the Connecticut-New York border is the luxurious and charming town of New Canaan. It is a gorgeous township known for its modern architecture, including the famous Glass House and the Tirranna Frank-Lloyd House. You can visit the stunning Glass House by buying a ticket online; however, the Frank Lloyd House is currently for sale. 

Spend the day exploring Irwin Park's nature trails near the town's center. This park is well-known for its gorgeous flowers on a 36-acre lot. Visit the nearby New Canaan Nature Center to see local wildlife and participate in annual events. Drop by Migota Boba for fantastic food and drinks. In particular, try out their various boba teas and milk beverages!


The Joseph Conrad boat at Mystic Seaport, Mystic
The Joseph Conrad at Mystic Seaport, Mystic.

Two hours east of New Canaan is the picturesque seaport community of Mystic. Visitors will still see finely crafted boats and vessels tied up at the docks. The Pequot people called this region home for centuries before the arrival of Europeans, but they later suffered significant losses during the Pequot Wars. In 1638, the Treaty of Hartford ended the fighting in the area.

Mystic offers boaters, anglers, and water enthusiasts several opportunities today. The Mystic River borders the community, and much as the name suggests, this waterway is a pristine and beautiful location. Take a day or evening cruise with the Argia Mystic Cruise! Get a table at The Mariner Restaurant for fresh, delicious, top-notch seafood served in a stunning environment by the sea. If you're traveling with history-loving people, consider booking a few nights at the lovely 1853 Captain Wheeler House!


White facade of the first congregational church of Litchfield Connecticut.
First congregational church of Litchfield, Connecticut.

Sitting in northwest Connecticut, Litchfield is a welcoming community filled with a charming blend of nature and Revolutionary War-era homes, shops, and designs. It is an ideal location for indulging in the beauty of the wilderness, all while getting a glimpse of America's founding.

Lourdes in Litchfield is a gorgeous shrine anyone visiting town should stop by and see! It's just a few miles north of Topsmead State Forest, the perfect place for hiking, biking, fishing, and outdoor adventures. Stop by the White Memorial Conservation Center for a front-row view of the local wildlife. Afterward, sample delicious ice cream at Peaches and Cream Ice Cream Shop.


Fall Colors in Kent, Connecticut and waterfront homes
Fall Colors in Kent, Connecticut.

Thirty minutes west of Litchfield is the chic, charming town of Kent. This quaint, quiet community is best known for its gorgeous forested regions, many local parks, and open spaces. If you want to visit a location with the perfect balance of nature and charming downtown shopping centers, then Kent is the right choice. The Kenise Barnes Fine Art collection is one of the loveliest sites in town, with a unique collection of local and up-and-coming artists in their various annual art exhibitions.

Visit Pond Mountain Natural Area and Macedonia Brook State Park for the perfect immersion in the surrounding natural splendor. Macedonia Brook State Park offers visitors a chance to hike the Blue Trail, granting one of the most splendid views of the Catskill Mountains! Visit Kingsley Tavern after a long day hiking and exploring for decadent salmon, yellowtail tuna, and plenty more!


Book Barn in downtown Niantic, Connecticut
Book Barn in downtown Niantic. Image credit Rachel Rose Boucher via

Nestled right along Niantic Bay and the Long Island Sound is the splendid little coastal town of Niantic. A designated census area of East Lyme, Niantic traces its history several centuries before its official establishment in the 1800s. It gets its name from the Native tribes in the region, particularly the Niantic Natives, who were members of the Algonquian-speaking Tribal group.

Several areas in Niantic still retain native names, including Oswegatchie Hill and Lake Pattagansett just north of the neighborhood. However, there's no need to leave the town to experience the natural glory of this community. McCook Point Park, located near the shore, is a great place to visit if you enjoy the beach and a trek in the woods! Check out Pine Grove Spiritualist Camp in the north of town for a calming experience. Although most of their events require registering, you can also explore the surrounding region and let the weight of life melt off your shoulders.


The old rustic shed on the left and bunch of colorful boat fenders in the middle in Southport, Fairfield, Connecticut.
The old rustic shed in the middle in Southport, Fairfield, Connecticut.

Resting along the Long Island, like Niantic, is the equally charming neighborhood of Southport. This beautiful town affords stunning historic sites and Victorian-style designs. The area along Harbor Road is particularly spectacular, with many shops and restaurants to keep your interest peeked all day. Visit Kasson's Jewelry for charming gemstones in a family-owned shop. They even offer estate jewelry with rich family histories. Just a few buildings down the road is the tasty Horseshoe Cafe! This is an excellent place to finish your town trip and meet friendly locals.

However, if you're more of a history lover, visit the Southport Historic District. It's not far from the Long Island Sound, meaning you can also take the opportunity to swim, fish, or beach comb along the shore!


Villa Bella Vista, Chester, Connecticut.
Villa Bella Vista, Chester, Connecticut. Image credit JERRYE & ROY KLOTZ. M.D. CC BY-SA 4.0 via Wikimedia Commons

Just north of Old Saybrook is the beautiful city of Chester, nestled right along the Connecticut River. Known for its ideal shopping center, breathtaking parks, and stunning waterways, Chester is perfect for a weekend getaway. Pattaconk Recreation Area is one of the town's main attractions, offering picnic areas, hiking paths, and plenty to do for the whole family. Bring your mountain bike or skis if you visit in the winter, and enjoy outdoor adventures.

Also, be sure to explore Chakana Sky Alpacas. This unique alpaca sanctuary strives to preserve the organic culture of the Andean Inca and bring people one step closer to nature. If you love cute animals and want to be part of something bigger, this spot is a must-see.

Sandwiched between New York City and Massachusets, Connecticut is sometimes overlooked for its larger neighbors. But that's unfortunate since this state offers a diversity unlike any other! With delicious restaurants resting along the seashore, mountain hikes, and freshwater fishing, you'll never be bored when exploring the great outdoors in Connecticut. If you prefer sightseeing, check out the many art studios, rustic, old landmarks, and spectacular shopping centers. Many of the shops and restaurants in these small towns are family-operated, so you can feel good about supporting local businesses all while having a great experience!

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