There are so many charming towns to check out in the Northeast, yet many travelers haven’t spent much time in the state of Connecticut. It’s one of the best places to view colorful fall foliage in the U.S., but there’s so much more here than just leaves and trees. There are lots of museums here (some of which you can visit for free!), top-notch restaurants to satisfy any foodie, and amazing coastal towns that’ll get you into the spirit of relaxation in no time. There are lots of locally owned shops and B&Bs here to soak up the history and culture of Connecticut. It’s an easy getaway from most major cities in the Northeast, which makes Connecticut perfect for a weekend trip.
So here are some of the historic and quaint towns to add to your travel list as you explore Connecticut.
Kent
The town of Kent is one of the top Connecticut destinations for travelers seeking a fall foliage road trip. This colorful town is full of everything you need to stay entertained and busy, yet relaxed, for a weekend. There are boutique shops, antique stores, indie cafes, and winding trails here. Go just outside to experience some of the best nature you’ll find in the entire state. There are a couple of state parks here, including Kent Falls State Park and Macedonia Brook State Park to explore waterfalls, hilltops, and bask in the blissful peace and quiet.
Westport
If you’re looking for a quick and easy getaway from New York City, then Westport is a top choice in Connecticut for you. This scenic small town is colorful with brick buildings along the waterfront and historic buildings that date back to American Colonial times. This is a great place to slow down your pace of life with a picnic in one of Westport’s relaxing green spaces. While in Westport, catch a performance at the Westport County Playhouse, relax on Compo Beach and at Sherwood Island State Park, and browse the local goods at the Westport Farmer’s Market.
Stamford
Stamford has a vibrant downtown area, not just in the fall, but all throughout the year. There are over 80 restaurants, bars, shops, theaters, galleries, and services here, and this is an ideal place to plan an affordable family vacation. One top attraction is Cove Island Park, which has train rides, beaches, volleyball, and a lawn that’s perfect for flying a kite. You can check out the Sound Waters Aquarium, the Stamford Museum & Nature Center, and Bartlett Arboretum and Gardens to learn about nature and entertain the whole family. If you have kids, the Twin Meadows Boundless Playground is a great place to play. For a night out, check out a show at the Curtain Call theater or a concert at the Palace Theater. Half Full Brewery is a great spot to grab a pint at the end of a day of sightseeing.
Cornwall
Cornwall is a small Connecticut town that is famous for its historic covered bridges. These bridges were built in the 19th century and are still useful as a form of infrastructure today. Other buildings throughout town are quaint and historic as well, so this makes a wonderful place to drive around on your fall foliage trip in the Northeast. While you’re in the area, you can also visit the even smaller town of West Cornwall to see the bridge. Mohawk State Forest is worth a visit to climb to the top of the mountain here as well.
Mystic
The Mystic Seaport is one of the top attractions in the entire state, so make sure to check out this living history village while you’re in the area. This is an 18th-century maritime settlement where you can tour historic ships, homes, a schoolhouse, and authentic town businesses. There’s lots more to do in Mystic as well, including art galleries, pizza places, shops, and the aquarium. As you walk along the main street in Mystic, you’ll find Colonial period homes, top seafood restaurants, the famous Mystic Pizza restaurant, and small shops. The Mystic Outdoor Art Festival takes place each year and draws tens of thousands of visitors each year to see the booths and displays from local artists.
Bristol
If you enjoy museums, then one of the best places to visit in Connecticut is Bristol. There are lots of museums here to check out, including the American Clock and Watch Museum, the Imagine National Museum, the New England Carousel Museum, and the Witch’s Dungeon Classic Movie Museum. As you can see, there is a little something for everyone in Bristol’s museum scene. When you are here, you can also check out the Harry C. Barnes Memorial Nature Center and Lake Compounce & Crocodile Cove, which is a family theme and water park. Page Park is a good place to play a game of disc golf, and Rockwell Park is a nice place in the West End to bring the kids to run and play.
Woodbury
Woodbury, Connecticut is a nice wintertime destination because the Woodbury Ski Area is located here. Other top things to do in Woodbury include the Walker Road Vineyards for wine tasting, the Flanders Nature Center trails for hiking, and the Glebe House Museum & The Gertrude Jekyll Garden to learn about local history. Foodies will enjoy the New Morning Market, the El Camion Mexican restaurant, Good News Café, and John’s Café. One of the best places to stay here is a boutique hotel called the Milestone Inn, which is close to the Quassy Amusement Park, Kettletown State Park, and lots of antique shops.
Chester
The town of Chester began as a shipbuilding and milling town, and it has well-preserved historic architecture still today. It’s easy to be entertained if you enjoy a small-town arts and culture scene because there are several art galleries and a theater here. You can also enjoy the great outdoors on foot when you visit Chester because there are some nice hiking trails nearby.
Wethersfield
Another Connecticut town that’s steeped in history is Wethersfield, which dates all the way back to 1634. Among the oldest and best-preserved buildings are the Buttolph-Williams House, the Joseph Webb House, and the Silas Deane house, all of which are on the National Register of Historic Places. If you head just outside of town, you’ll see plenty of natural beauty too. There are lots of trees, winding trails, and open meadows to let your mind quiet down and observe your serene surroundings.
Old Saybrook
Old Saybrook is a waterfront town in Connecticut that makes for a wonderful weekend getaway. Like many Connecticut towns, it’s filled with historic homes, old-fashioned fixtures, and friendly people. It was once even home to Katharine Hepburn. Make sure to see the historic lighthouse and visit the soda fountain that’s been here since the late 1800s. There’s a nice Main Street here with locally owned mom-and-pop shops to browse.
Greenwich
Greenwich is a popular Connecticut town to visit because it’s so close to New York City. You can hop on a train in Manhattan and get here in under an hour, and if you don’t mind a commute, you could even live here and work in the city! As you walk through town you’ll experience an upscale vibe with designer boutiques and high-end fashion. The Bruce Museum is located in downtown Greenwich near the harbor and features anthropology, natural history, and art. The best beach in the area is Greenwich Point Park, where you can go boating, do water sports, hike along the trails, and get nice views of the NYC skyline.
