These 8 Towns In Connecticut Were Ranked Among US Favorites In 2026
Peaceful New England village greens and colonial architecture dating back to the 1600s make up just a part of what Connecticut has to offer visitors. The shoreline runs along the bays and inlets of Long Island Sound where sandy beaches abound and fresh seafood is served on the water in warm weather. Inland you'll find county fairs and miles of hiking trails and waterfalls plus easy proximity to major metros for day trips and weekend jaunts. If you love the water, head straight to Old Saybrook or Madison. History turns up in almost every town we recommend, and Mystic in particular is full of museums. Kent is the place to go if hiking is at the top of your list.
Litchfield
Litchfield's town green will pull you right into the colonial era from the moment you arrive. For this reason and others, it's long been considered one of Connecticut's prettiest towns. It's packed with small shops, art galleries, and antique stores. Jeffrey Tillou Antiques has been in the same place on the green for 30 years. The Litchfield Inn is just one of many historic buildings in town and if you are a history buff, you will also want to visit the Tapping Reeve House and the Litchfield Law School, the first law school in the US, established in 1784.
Feel as though you've traveled to a bit of England in Topsmead State Forest, with its English-style grounds and the Edith Chase cottage. This Tudor-style cottage is home to Chase's large collection of art and antiques. Hike to a tower to view the beautiful surrounding scenery (there are 510 acres of it). There are also nearby wineries and miles and miles of country drives.
Catch the Goshen Fair, just a few miles away, over Labor Day if you love carnival rides, food stands, and farm and craft contests.
Westport
Westport's easy access to New York City has made this a popular weekend destination for decades; it's a 55-mile drive by car or a short ride on the commuter train. But that's just one reason of many that has made this town a favorite destination for so long. The thriving arts scene is headlined by Westport Country Playhouse, with its famous red barn exterior. Originally built in 1835, it became a world-renowned theater in 1931, initially serving as a tryout for Broadway bound shows and tours of summer stock plays and musicals. It is still in business today, hosting touring shows and concerts. There are also summer concerts at Levitt Pavilion, art galleries, and summer art fairs.
In between all of that, take a breather at Compo Beach or nearby Sherwood Island State Park. With playgrounds and spots for grilling, both are great for families and just hanging out in the sun. This area, along with much of Fairfield County, is quite affluent and a great place to drive around to see impressive houses and yachts parked in marinas.
Mystic
The town of Mystic is home to the largest maritime museum in the US, Mystic Seaport. You'll find hundreds of carefully restored historic vessels, such as the famous Charles W. Morgan, the last surviving whaler in the world. Alongside is a working port where you can explore the many industries that supported maritime activity in the 19th century, such as a recreated rope factory and a sail making building. Watch boats being repaired using historically accurate tools and methods. Adjacent to the port is a recreated seafaring village that houses more than 60 authentic buildings that have been moved here from around New England. Artisans, dressed in old-time clothing, demonstrate cooking, coopering, and much more. You can also visit the planetarium that's on site and go for short rides on rowboats, sailboats, and a launch.
Mystic Aquarium is another big draw in this town. It's one of the few places in the US to see beluga whales. There are touch pools, a rain forest, and the option to interact directly with some of the animals for an additional fee.
Mystic is increasingly becoming known as a foodie town. Abbott's Lobster in the Rough is less than four miles from the Mystic Seaport and serves freshly caught clams, chowder, and lobster right by the water.
Guilford
Do you want to feel as though you have stepped right into the popular television series, Gilmore Girls? Even if you aren't a fan of the show, you will love Guilford if a cozy, coastal village sounds tempting. The town was settled in 1639 and features one of the largest collections of historic homes in New England. The Henry Whitfield State Museum is housed in the oldest stone house in New England. The village green is a full 12 acres and surrounded by even more colonial-era homes. The First Congregational Church has been in existence, in three different buildings, since 1713. Said to be the first church in Connecticut to have a steeple clock and bell, you will recognize it as the model for dozens of other New England churches built afterward.
Bishop's Orchards is a large farm market and winery that has been in place for generations. Apple picking, fresh pies, and hard cider are earmarks of this establishment. There are many other local farms and wineries to tour in the surrounding area. Of course there are the coastal beaches, including the 25-acre Jacob's Beach. Timberland Preserve is a great place for hiking, horseback riding, or biking on trails. Fishing is also possible with a license.
Madison
Hammonasset Beach, right outside the town of Madison, is the most popular beach in Connecticut. Massive, it boasts two miles of white, sandy beach, with boardwalks, food stands, and a campground. More outdoor recreation can be had at Bauer Park, a nature preserve, and a covered bridge that spans the Hammonasset River. There are miles of trails, including some that follow the shoreline.
The Boston Post Road, once the main "highway" for the colonies, runs right through this town. Along it you will find numerous boutiques, shops, and bakeries. The most famous of these is R.J. Julia, an independent bookstore that draws visitors (and world class author talks) from all over New England. The town green, also along the Post Road, dates to 1705 and is a hub for warm weather concerts, picnics, and a year-round farmer's market.
Kent
Gorgeous natural beauty is the earmark of a visit to Kent. It's set in the rolling Litchfield Hills, which reach the nearby New York border. Start with a trip to Kent Falls State Park, cross over a covered bridge, and hike up a stone stepped trail to view the 250-foot-high waterfalls. As well, the Appalachian Trail runs through this area and Macedonia Brook State Park is a great place to camp and hike. Connecticut is generally vivid during fall leaf season, but Kent has been recognized as one of the most brilliantly colored. Nearby Bull's Bridge is one of few wooden covered bridges that still exist in Connecticut, crossing right over the Housatonic River.
In town, there is plenty to do to rest up after a day of outdoor recreation. Visit an independent book shop, eat out, and visit art galleries. Over the New York border, into Dutchess County you will find more arts opportunities and hiking, such as Dover Stone Church Preserve, a dramatic, cathedral-like cavern.
Old Saybrook
You'll find the perfect blend of Connecticut's rich history and scenic shoreline in Old Saybrook. Founded as a plantation in 1635, it ranks among Connecticut's oldest towns. Locals love to boast about Katharine Hepburn, who spent much of her life in her family's home on the outskirts of town, Fenwick. You can't visit it, but you can go to a museum and theater in town that is dedicated to her life and legacy. Beyond that, the location is the true star of this shoreline town, which is where the Connecticut River meets Long Island Sound. This was once a major port, back in colonial days. There are over a hundred historic homes in town.
Spend some time on the sand of Harvey's Beach and visit the Lynde Point Lighthouse and Saybrook Breakwater Lighthouse for a further taste of Old Saybrook's rich seafaring history. The Old Saybrook Historical Society has even more information about the rich background of this area.
A special day trip is to the Goodspeed Opera House, the producer of over 300 musicals. This company was the first regional theater to win two Tony awards, one for its outstanding contribution to the American musical genre. The Goodspeed is in East Haddam, along the Connecticut River, about 20 miles away from Old Saybrook.
Putnam
Putnam was once a mill town that was mostly destroyed by debilitating floods in 1955. The town was able to restore many of the abandoned brick mill buildings, giving birth to this town's rich arts culture. It's also known as the "Antique Capital of the Northeast". You'll find close to a dozen antique shops in town and more in the surrounding area. The Antique Market at Bugbee's is on Main Street and has 22,000 square feet of shopping. Right in town are art galleries, restaurants, and boutiques.
Seasonal festivals are another big draw to this town, including River Fire, where bonfires are set along the Quinebaug River, accompanied by live music. Bring a picnic or order in from one of many fantastic restaurants that this town is increasingly becoming famous for. There are also abundant hiking opportunities in nearby forests. For experienced trekkers, Mashamoquet Brook State Park offers rugged, technically complex trails and a number of famous geological markers, such as Table Rock and Indian Chair. Airline State Trail is a 60-mile rail trail that offers a more moderate hike and bike experience.
Connecticut's US-Favorite Towns
Almost every Connecticut town we've described here is close to outdoor recreation, hiking, history, and the arts, making it hard to choose just one!
