7 Perfect Destinations for a Long Weekend in Connecticut
Connecticut's small towns provide uncrowded destinations for a more relaxing long weekend trip. For example, Niantic has a small "hole-in-the-wall" beach that connects many other attractions, from a beachside bluff to an innovative children's museum. New Canaan, meanwhile, invites guests to explore buildings and enclosed trails where the walls are made of pure glass. Visitors can also discover Appalachian nature trails, such as Litchfield's more than 15 waterfalls, or a mountain hike that offers views of multiple states in New England. These are just a few of the activities guests can do in these 7 destinations, which are perfect for a long weekend in Connecticut.
Kent
Kent is located in one of the most scenic counties in Connecticut: Litchfield. First settled in 1737, it has retained a distinctly old world field with multiple boarding schools, and one of the three remaining covered bridges in Connecticut: Bull Bridge. Built in 1842 in a lattice truss design, cars and pedestrians still go across this bridge to this day. What really makes the town worth staying at is Kent Falls State Park, an Appalachian destination with 17 waterfalls to explore. The largest is Kent Falls itself, which drops 250 feet down the Housatonic River. Kent houses several museums that paint a picture of life throughout the centuries in New England, such as antique farming equipment at the Connecticut Antique Machinery Association Museum and the Seven Hearths Museum, which was an important home and business center in Kent from its construction in 1751. You have several options for accommodations in Kent, from a cute blue train car turned into a hotel called The Train Car to the Victorian 1800s hotel.
New Canaan
New Canaan is firmly located in the Gold Coast of Connecticut, and this is reflected in its beautiful and unique architecture. The town's most intriguing home is the Glass House, built between 1949 and 1995 by architect Philip Johnson on a lush garden estate. Every wall is made of glass, letting in natural light, and the grounds around it are filled with sculptures. This isn't the only glass structure in town, as Grace Farms has a winding glass-enclosed enclosure under one continuous roof, featuring exhibits and farm-based activities and programs. New Canaan has a more traditional mansion at the Waveny House, built in 1912 in the popular Tudor Revival style on 300 acres. There's a city park right outside of the house called Waveny Park with a pool, sports courts, and a formal garden space. You can enjoy your weekend stay here in style at the Roger Sherman Inn on a renovated 250-year-old property.
Niantic
Niantic is a great destination for families with its children's museum and hidden beaches. Located on the Long Island Sound, it has several beaches to visit, but the most unique one is the Hole in the Wall Beach. You have to pass through a small tunnel underneath railroad tracks to reach this small beach, home to many seagulls, which features a boardwalk and swimming area. The beach also connects to McCook Point Park & Beach, a bayside bluff with two beaches on both sides. A short walk away from the Hole in the Wall Beach is the Niantic Children's Museum, with exhibits encouraging them to learn and discover on their own through the interactive Discovery Room, Imagination Room, and others. After visiting the children's center, you can check in for the night at the Niantic Inn in downtown Niantic.
Mystic
Out of all of Connecticut's maritime towns, Mystic is one of the most highly regarded. It was once the biggest shipbuilding town in Connecticut, and today it maintains the last wooden whaleship in the world: the Charles W. Morgan. You can see this boat at the Mystic Seaport Museum, which also hosts a 19th-century seafaring village and a ride on the Mystic River in the Liberty sailboat. You can rent a motorized boat to take out on the coastline via Mystic Boat Adventures or kayak and paddleboard from Adventure Mystic. To get out onto the beach, you can go to the Williams Beach Park. Mystic also has one-of-a-kind souvenir shops that aren't common elsewhere, like Mystic Knotwork, which makes bracelets made out of nautical rope. There are several inns close by to these attractions to stay at, from the Hilton Mystic to the Inn at Mystic.
Litchfield
For nature lovers, Litchfield is the best destination on this list. It sits between two state parks: Mt. Tom State Park and Topsmead State Forest. Mount Tom has a panoramic view of the Catskills, Long Island Sound, and the Taconics once you hike up a one-mile trail to a black tower nestled on the summit. Topsmead State Forest is a storybook destination that was previously the home of Edith Morton Chase, who left the land to the state when she died. Her English Tudor-style cottage is still on the property, along with hilly nature trails, diverse bird habitats, and an Oriental Family Butterfly Garden and Viewing Stand. These landscapes inspire quite a bit of art as well, which you can view at the Jennifer Terizan Gallery, which focuses on contemporary art styles. Book your stay in the historic section of Litchfield at Belden House & Mews, a 3-acre hotel with 31 guest rooms.
Old Saybrook
Old Saybrook was initially settled by the Dutch in 1624, but they abandoned it for the more lucrative colony of New Amsterdam. English settlers would take their place not long afterward, and they fought several vicious battles with Native Americans during the Pequot War. Today, Old Saybrook is a charming Long Island Sound destination, with beaches, boardwalks, and the home of a famous 20th-century actress. There's the small and relaxing Harvey's Beach on the sound for swimming or relaxation, while the Saybrook Point Marina provides a central location for tours or exploring the sound on your own. One of the best ways to explore Old Saybrook is to go on the boardwalk at the Fort Saybrook Monument Park, which explains the history of the area through sculptures. Lastly, Old Saybrook was the summer home of actress Katharine Hepburn, who was herself a native of Connecticut. The Katharine Hepburn Culture Arts Center collects artifacts from her movies, special screenings, and shows. While staying in this coastal town, you can take in views of the Sound at the Water's Edge Resort & Spa.
Woodbury
Founded in 1673, Woodbury has a large stretch of historic buildings going back to the 1700s, including many that resemble ancient Greek temples. The most iconic structure in the town is King Solomon's Lodge No. 7, a Freemason lodge chartered in 1765 that was built in the Greek Revival style like a temple. This lodge dedicates itself to local charity work, collecting food and supplies from a supermarket. Visitors can also pay a visit to the Glebe House Museum, built around 1740 for an Anglican priest in the center of the village. Today, it maintains 18th-century furniture and a garden. Woodbury also preserves so many antiques that it has been called the Antiques Capital of Connecticut. Going on the Woodbury Antiques Trail will take you to several of these antique shops, such as Villa Vintiques. There are multiple nature preserves around Woodbury that you can check out at the Flanders Nature Center & Land Trust. For a spot to stay in this town, there's the 1754 House, which offers inn rooms and a restaurant.
Connecticut is filled with hole-in-the-wall places that are ideal stops on a long weekend trip. Some of them are historic museums like the Glebe House Museum, while the Hole in the Wall Beach rises up to meet you while passing under a railroad tunnel. Of course, some are local businesses that have unique products like the rope bracelets at Mystic Knotwork or the multitude of vintage and antique goods along the Woodbury Antiques Trail. Regardless of which town you pick for your long weekend getaway, you'll have lots of "hole-in-the-walls" to choose from.
