Downtown New Canaan, Connecticut. Image credit: Miro Vrlik Photography / Shutterstock.com.

The 7 Can't-Miss Towns In Connecticut

As the third-smallest state in the US, Connecticut is sometimes overlooked in conversations about the most exciting places to visit on vacation. However, despite its size, the state has an incredibly diverse mix of towns. Towns like Old Saybrook and Mystic offer a classic New England coastal experience with clam chowder and sailing charters, while places such as Cornwall and Essex reflect the traditional New England style many associate with the region. If you are looking to explore some of the most phenomenal destinations in Connecticut, these seven should be on your itinerary.

Old Saybrook

The Connecticut River flowing along Old Saybrook, Connecticut.
The Connecticut River flowing along Old Saybrook, Connecticut.

Sitting where the Connecticut River meets the Long Island Sound, Old Saybrook is an adorable coastal community with plenty to do near the water. Travelers can start out their exploration of town at The Preserve, a 963-acre piece of land that is considered to be the largest remaining unprotected coastal forest between New York and Boston. Afterwards, head to College Street for a game of putt-putt at Mini-Golf at Saybrook Point, a charming golf course along the Connecticut River. If you get hungry, there are plenty of places to enjoy some hearty seafood in town. Liv’s Shack is a town favorite, serving lobster rolls, shrimp tacos, clam and chowder, among other delicious seafood dishes.

New Canaan

Downtown New Canaan, Connecticut
Downtown New Canaan, Connecticut. Image credit: Miro Vrlik Photography / Shutterstock.com.

Located in southern Connecticut near the New York border, New Canaan has a thriving cultural scene showcased through several attractions. One of the most prominent is The Glass House, constructed between 1949 and 1995 by the famous architect Philip Johnson. Surrounded by a serene pastoral landscape, travelers can explore the property, browsing its permanent collection of 20th-century works. To continue your tour of town, head over to Grace Farms, an 80-acre humanitarian center that has art exhibits, events, and natural displays that promote human justice and community. If you want to see more of the area’s natural beauty, spend a few hours at the New Canaan Nature Center, which features aviaries with Birds of Prey, a children’s play garden, a nursery, a scavenger hunt, and more.

Essex

Essex, Connecticut.
Waterside homes in Essex, Connecticut.

Essex is a classic, New England-style village that continues to preserve its maritime heritage through its museums, festivals, and railroads. The Connecticut River Museum is the perfect place to begin your trip, housed in a 19th-century Steamboat dock building and offering three floors of exhibits that recount over 12,000 years of the area’s history. The town’s history further comes to life on the Essex Steam Train & Riverboat, the only steam train and riverboat connection in the country. This two-and-a-half-hour narrated ride takes passengers through the scenic Connecticut River Valley. You may also consider planning your trip to Essex in June, during the Connecticut Sea Music Festival. This annual event celebrates the region’s maritime and traditional music through performances, educational activities, and community events.

Cornwall

West Cornwall Covered Bridge Connecticut.
West Cornwall Covered Bridge Connecticut.

Divided into five cozy villages, Cornwall perfectly embodies that small-town charm that many people associate with Connecticut. There are plenty of local shops and boutiques to browse throughout town, such as The Wish House, an eclectic shop that sells gifts, home decor, clothing, and crafts made by artisans from around the world. The town’s history is preserved in landmarks such as the West Cornwall Covered Bridge, one of the last remaining covered bridges in the state. Extending 172 feet long by 15 feet wide, this bridge, which is listed on the National Register of Historic Places, has preserved the state’s rural history and heritage for nearly 160 years. To enjoy a bit of the town’s surrounding countryside, travelers can appreciate a hike on the Pine Knob Loop Trail, located in the Housatonic State Forest and Housatonic Meadows State Park. This trail, while short and challenging, will give you incredible views of the River Valley from above.

Chester

Green gate for Chester-Hadlyme Ferry in Chester, Connecticut
Green gate for Chester-Hadlyme Ferry in Chester, Connecticut. Image credit: Rachel Rose Boucher / Shutterstock.com.

Chester is the perfect town to visit if you are seeking a laid-back, Connecticut-style vacation. Start your day with a visit to the Cockaponset State Forest, the second-largest state forest in Connecticut, where you can enjoy a variety of activities like hiking, mountain biking, fishing, and swimming. Afterward, hungry travelers can grab lunch or dinner at Marker 37, a riverside restaurant with a waterfront patio and music nights in the summer. Little House Brewing Company is another relaxing place to spend an hour or two, a local brewery that is set in a small home that dates back nearly two centuries. Here, a few of the beers you can order include lagers, IPAs, and stouts.

Mystic

Mystic Seaport in Mystic, Connecticut
Mystic Seaport in Mystic, Connecticut. Image credit: Faina Gurevich / Shutterstock.com.

If you are looking for a summer filled with seaside fun, Mystic is an excellent destination to have on your radar. Several companies in the area offer cruises and charters, such as Argia Mystic Cruises, which offers day sails and sunset cruises on the town’s only remaining sailing ship. The Mystic Seaport Museum is another interesting attraction, offering water tours on a historic vessel, workshops and classes, and maritime-related exhibitions to explore. Those in town on Sundays should swing by the Denison Farmers Market, which takes place from June through October, selling high-quality produce, fruits, and other locally produced goods from the region.

Canterbury

Side view of the Prudence Crandall Museum in Canterbury, Connecticut
Side view of the Prudence Crandall Museum in Canterbury, Connecticut. Image credit: Rachel Rose Boucher / Shutterstock.com.

Situated in the eastern Connecticut countryside, Canterbury has an active agricultural community, with lots of local farms and culinary establishments to visit in the surrounding area. Travelers interested in learning about the local farming practices can visit Baldwin Brook Farm, a raw milk dairy farm that offers tours of the facilities and the chance to see some of the Jersey cows. For more dairy fun, head over to Wicked Cow, a family-owned ice cream shop that has more than 30 flavors of ice cream to choose from! To connect with nature, consider camping or hiking at the Kinne Preserve, a 28-acre wooded property with 1.2 miles of hiking trails and a small camping area.

Final Thoughts

While charming Connecticut towns are abundant, the seven listed above act as a wonderful starting place for your state tour. Quiet farms in the countryside, seaside restaurants, steam trains, riverboats, and celebratory maritime festivals are just a few of the attractions that await in these towns. The summer is not over yet! Make the most of August’s warm, sunny days by exploring all the beauty and activities these beautiful Connecticut towns have to offer.

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