7 Unforgettable Small Towns to Visit in Connecticut
Connecticut is a small state located north of New York Island and New Jersey, with Upstate New York to the west, Massachusetts to the north, and Rhode Island to the East. The state houses 142 state parks throughout its borders, which grants visitors some breathtaking views of the rolling hills and rivers painting its landscape. The Connecticut River is its most notable river, traveling an area of over 410 miles. Mount Frissel is its highest point and is an exciting hike for any skilled mountain climber.
Connecticut also has gorgeous little towns that are filled with small-town charm and hospitality. Each town is unique in its own way, and tourists through the communities will surely enjoy the local historic locations and natural sites.
Mystic
Mystic is a stunning township that sits along the southern coast of Connecticut, with the Block Sound and Fisher Sound separating the state from New York Island. The Mystic River flows through the town center and empties into Mystic Harbor and the Atlantic Ocean. The community began as a ship-building and whaling town in 1654, which is still evident to anyone who visits today.
Mystic has several beautiful marinas and coastlines that showcase its heritage and natural beauty. Safe Harbor Mystic in the southeast of town is the perfect spot to catch both of these aspects of the town, with several gorgeous ships, fabulous fishing grounds, and views of the sprawling harbor.
Just south of Mystic is Williams Beach Park, an ideal place for families hoping to enjoy swimming, beachcombing, and much more. Guests looking to glimpse Mystic’s founding should also drop by the Mystic Seaport Museum. They also host several events yearly and have a superb display of local Blaschka Marine Invertebrates.
Westport
Westport is approximately an hour and a half west of Mystic and is another charming coastal town along the Long Island Sound. It’s well known for its beauty, which inspired artists for decades, as the rolling hills and woodlands create an atmosphere of inspiration and creativity. The Saugatuck River cuts through the town’s center and adds to the calming and overall peaceful atmosphere of the community.
This river is also an excellent location for fishing and hiking, with the river’s trout and salmon site offering plenty of exciting fishing opportunities. Traveling down to the south of town are two gorgeous parks along the coastline, Westport Longshore Club Park and Sherwood Island State Park. Both of these parks provide fantastic views of the ocean, but they’re unique. Longshore Club Park is perfect for golf enthusiasts, while Sherwood Island State Park is better for anyone hoping to hike or bike in nature.
Those seeking to experience and celebrate the town’s artistic heritage should visit Onion Hills Design, LLC. This location celebrates a local artist, Kassie Foss, with originals and wholesale paintings for sale that primarily showcase the natural glory 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 beautiful town nestled along the border of New York, approximately twenty minutes southwest of Cornwell. The town dates back to 1739 and primarily consisted of farmers and iron ore manufacturers. The Kent Historical Society strives to preserve the town’s history, mainly focusing on the art and cultural significance of the past. Kent is a favorite site for painters and artists, thanks to the sprawling hills, mountains, and valleys creating gorgeous natural backdrops.
One of the most beloved locations for walks in the woods or photographs is the Bulls Covered Bridge, which crosses over the Housatonic River. North of the covered bridge is Kent Falls State Park, the perfect spot for a moderate hike in the rocky regions of the forest. East of Kent Falls is another beloved outdoor location, Macedonia Brook State Park. For those seeking a more intense hiking experience, this site is ideal.
With so many outdoor activities to enjoy, people will surely develop an appetite. Bulls Bridge Inn, located right along the Housatonic River near the covered bridge, is a great place to finish the day. They serve classic American dishes in a welcoming environment, along with delicious cocktails and beverages.
Monroe
Monroe rests around an hour south of Kent along Lake Zoar and is one of Connecticut's most picturesque towns. Although not as old as some of its neighboring towns, with its official founding beginning in 1823, Monroe has a rich environment and culture to share with the world. The people pride themselves in prioritizing family in their close-knit community, offering guests a break from the chaos of life in a welcoming small town.
By far, Webb Mountain Park is an idyllic location to break away and indulge in the wilderness. For those planning an extended stay in town, this park has several campgrounds that grant excellent forest views in a clean and organic atmosphere. Wolfe Park, located near the southern parts of town, is another popular outdoor site with several trails like the Rails and Trail Bike Path, which is perfect for any cycling enthusiasts.
Boat lovers will love this town as well, with the Zoar River providing awesome opportunities for boating and fishing. The Monroe Town Boat Ramp isn’t far from the Stevenson Dam and is the best launching site.
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.
