7 Unforgettable Small Towns to Visit in Connecticut
Connecticut has a knack for making a regular Saturday feel like a mini reset. One weekend, you’re doing a harbor stroll in Mystic, the next, you’re watching the Saugatuck River roll by in Westport, and another, you’re soaking up classic Connecticut River scenery in Essex. Some towns are made for shoreline time and easy marsh walks, like Old Saybrook around Plum Bank Marsh and the Black River area. Others lean into pure Litchfield Hills energy: covered-bridge photo stops in Kent and quiet forest miles near Cornwall in Wyantenock State Forest. Each town on this list works as its own day trip or simple overnight; pick the vibe you’re craving, follow our highlights, and you will not be disappointed.
Mystic
Mystic is a beautiful township located along Connecticut's southern coast, with Block Sound and Fisher Sound separating it from New York Island. The Mystic River runs through the town center, emptying into Mystic Harbor and the Atlantic Ocean. Originally established in 1654 as a shipbuilding and whaling community, this heritage remains visible today. Mystic features several scenic marinas and coastlines that highlight its natural beauty and history. Safe Harbor Mystic, in the southeastern part of town, offers excellent views of the harbor, with stunning ships and prime fishing areas. Just south lies Williams Beach Park, perfect for families seeking swimming, beachcombing, and other activities. For a glimpse into Mystic’s origins, visit the Mystic Seaport Museum, which also hosts several annual events and displays a remarkable collection of Blaschka Marine Invertebrates.
Westport
Westport is roughly an hour and a half west of Mystic and is a delightful coastal town along the beautiful Long Island Sound. Known for its stunning scenery, it has long inspired artists, thanks to its rolling hills and lush woodlands that create a sense of inspiration and creativity. The Saugatuck River runs through the heart of the town, adding to its peaceful and serene vibe.
This charming river is not only scenic but also perfect for fishing and hiking, with prime spots for trout and salmon that offer exciting outdoor adventures. To the south, you'll find two lovely parks along the coastline — Westport Longshore Club Park and Sherwood Island State Park. Both parks boast breathtaking ocean views, each offering a unique experience: Longshore Club is great for golf lovers, while Sherwood Island is ideal for hiking and biking enthusiasts.
For those interested in celebrating the town’s rich artistic spirit, be sure to visit Onion Hills Design, LLC. This wonderful spot highlights the talents of local artist Kassie Foss, featuring original paintings and wholesale works that beautifully capture the natural beauty of the area.
Essex
Essex is a lovely little town just over an hour east of Westport along the Connecticut River. This community traces its roots back to the Nehantic Indian tribe prior to the arrival of Europeans in 1648. Travelers to town can visit one of the many museums to see more of their fascinating history, including the Pratt Village Smithy and the Pratt Family Museum. These locations demonstrate well-preserved structures of the site’s early years and grant guests a unique glimpse into the history of a prominent family of Essex’s past.
Canfield Woods in the north of the community is one of the best nature sites for woodland lovers. Several trails of varying lengths cross through the forest, including Eagle Ridge Trail and Primitive Trail. Most of these trails connect and allow trekkers to explore the 300-acre woodland and showcase its many natural charms.
Griswold Inn is a fabulous historical inn located along the banks of the Connecticut River. This site goes back to 1776 and is one of the longest continually operated Inns in America, offering guests delicious foods served in colonial-era dining and tap rooms.
Old Saybrook
Old Saybrook sits directly south of Essex, touching the Long Island Sound to the South and the Connecticut River to the east. It began as Saybrook Colony in 1635, with John Winthrop serving as the colony’s governor. Visitors should stop by the Hart House and Exhibit Gallery to see one of the oldest standing houses in town, built back in 1767. Tourists should also stop by the nearby memorial where Yale College once stood between 1701 and 1716.
Since it sits along the Long Island Sound, the town has plenty of coastline and beaches worth exploring. Oyster Point, Cove Point, and Kolly Beach are three of the most notable and offer excellent views of local wildlife and the expanse of wetlands. Black River and Plum Bank Marsh Wildlife Area sit nearby and are excellent for a little hike or stroll through the marshes.
Cornwall
Approximately an hour and a half northwest of Old Saybrook is the stunning township of Cornwell. The town was incorporated in 1740 and primarily subsisted of farming communities and later grew to manufacturing and charcoal processing. The Housatonic River flows to the west and is one of the main waterways of the town. There are several beautiful parks along its banks, with the Housatonic Meadows State Park being one of the most charming and just outside the town’s border.
The Pine Knob Loop via Appalachian Trail to the south is another nearby site just west of town that lets travelers explore the Appalachian Trail. It typically takes approximately an hour and a half and traverses an area of around 2.5 miles. However, there’s no need to leave town to see the glorious beauty of the area.
Cornwell is home to Wyantenock State Forest, with Mattatuck Trail just east of the site. The forest is ideal for mountain hiking and biking and offers some spectacular views of the region. Mohawk Trail is very long, covering 42 miles and passing through several towns. However, this trailhead in Cornwell is a favorite site, and there’s no need to travel the entire expanse to enjoy Conecticut’s natural glory.
Kent
Kent is a charming town located along the border of New York, just about twenty minutes southwest of Cornwell. With roots dating back to 1739, it was originally home to farmers and iron ore manufacturers. The Kent Historical Society works hard to preserve and celebrate the town’s rich history, especially its artistic and cultural legacy. Kent is a favorite spot for painters and artists, thanks to its expansive hills, mountains, and valleys that create stunning natural scenery.
One of the most cherished places for peaceful walks or capturing beautiful photos is the Bulls Covered Bridge, which gracefully crosses the Housatonic River. Just north of the bridge lies Kent Falls State Park, a wonderful spot for a moderate hike through rocky forests. To the east, Macedonia Brook State Park offers another favorite outdoor experience—perfect for those who love a more vigorous hike.
After enjoying all these outdoor adventures, visitors often find themselves a bit hungry. The Bulls Bridge Inn, situated right along the Housatonic River near the covered bridge, makes a lovely place to unwind and enjoy a meal. They serve classic American dishes in a warm, welcoming atmosphere, along with tasty cocktails and beverages.
Monroe
Monroe is a charming town located about an hour south of Kent, nestled along the scenic Lake Zoar. While not as old as some of its neighboring communities, having been officially founded in 1823, Monroe offers a rich blend of natural beauty and vibrant culture. Its residents truly cherish family and community, creating a warm, welcoming atmosphere that provides visitors with a peaceful escape from everyday life.
For nature lovers, Webb Mountain Park is a wonderful spot to relax and immerse yourself in the wilderness. If you're planning a longer stay, you'll appreciate the park's several campgrounds, which offer stunning forest views in a clean and natural setting. Wolfe Park, near the southern edge of town, is another favorite outdoor destination featuring a variety of trails like the Rails and Trail Bike Path, ideal for cycling enthusiasts.
Boat enthusiasts will also find plenty to enjoy here, with the Zoar River offering fantastic opportunities for boating and fishing. The Monroe Town Boat Ramp, conveniently located near Stevenson Dam, is the perfect starting point for your aquatic adventures.
In Conclusion
Visiting Connecticut is the perfect opportunity to see the lovely charm of one of America's smaller states. Despite its small size, there's no shortage of incredible adventures to be had in this state. The many mountains, farmland, rivers, lakes, and miles of coastline make it a one-of-a-kind location. However, there are plenty of historic and artistic places to visit as well, with some of the oldest homes in America preserved within its boundaries.
Whether travelers want to scale a mountain, hike the woodlands, check out historic sites, or a blend of it all, Connecticut has plenty to offer.
