8 Ideal Destinations For A 3-Day Weekend In Connecticut
Connecticut is a lively and inviting state, situated halfway between New York and Boston. The state is most well known for its year-round adventure, with plenty of activities to enjoy no matter the season, such as skiing, golfing, hiking, outlet shopping, casino-going, and more. It is a popular spot to partake in a scenic drive or outdoor escapade; boasting breathtaking fall foliage, the enchanting Mystic Seaport, and the architecture and art galleries of New Haven give Connecticut it's timeless charm.
Old Saybrook
Situated where the Connecticut River meets the Long Island Sound, Old Saybrook is a charming coastal town, home to an inviting main street lined with shops, boutiques, and restaurants, as well as a welcoming community. Visitors immerse themselves in the town's culture at The Kate, which is the local theater with different live entertainment each week. Historic buildings tell tall tales of the past, while breathtaking views of the Atlantic from the Saybrook Breakwater Lighthouse (constructed in 1886) share a glimpse into the beauty of the present day. Enjoy a day spent relaxing on Harvey's Beach or kayaking along the glistening waters. For a game of 18 holes, visit Saybrook Point, or learn all about the town's history at Fort Saybrook Monument Park. Be sure to take a break in the great outdoors with a hike through the 1700 acres of coastal forest at The Preserve.
Greenwich
One of the most charming small towns in the state, Greenwich sits on Connecticut's Gold Coast and is just a short train ride from New York City. Greenwich Point Park features a scenic beach with a sandy waterfront and plenty of space for water sports and beachy activities, so be sure to bring a swimsuit or two! Another great spot to enjoy the outdoors is the Great Captain Island & Island Beach, where visitors can take a short ferry or water taxi and spend the day exploring the natural and welcoming environment.
The town's historic districts house buildings from the 1700s that are both architecturally and historically significant, such as the Second Congregational Church, Calvert Vaux’s 1861 Tomes-Higgins House, and the 1909 Christ Church. Enjoy a leisurely stroll through the downtown core, taking in the beauty of the buildings from the past, and stopping in at the local shops and antique spots with plenty of souvenirs and memorable objects.
Chester
The small town of Chester comes alive in summer, most well known for its natural environment, chock full of natural streams, waterfalls, and ponds, as well as lush and dense forests. Because of its appealing landscape, the town is the perfect summer escape. One of the top attractions is the Chakana Sky Alpacas, a small farm where visitors get to meet alpacas and shop a selection of unique goodies. The Chester to Hadlyme Ferry offers scenic views of the area, traversing across the Connecticut River near Gillette Castle State Park. For those with an interest in the downtown core, the main street boasts unique architecture and charming spots such as the Norma Terris Theatre. After a day well spent exploring the area, be sure to stop by Little House Brewing Company for some refreshments.
Westport
Westport sits along the banks of the Saugatuck River and is often considered one of the most beautiful cities in Connecticut, blending the appeal of its scenic location with a unique and intriguing culture. Westport boasts amazing views of the North Atlantic Ocean and sparkling river, with access to sandy beaches, water sports, and waterfront eateries. Compo Beach is a popular tourist destination for those looking for a day on the water, while Longshore Park is a great spot for a game of golf. Those with a sweet tooth may find themselves wandering towards Bridgewater Chocolate, where there is a broad selection of tasty treats, while the weekly Farmer's Market is the ideal spot for fresh fruits and goods. Levitt Pavillion features a plethora of performing arts shows, ideal for a day enjoying the outdoors, the community, and supporting local artists.
Litchfield
Boasting the charm of 18th-century New England, Litchfield is a scenic and historic town with plenty to do for a three-day weekend escape. Colonial-era architecture lines the downtown streets, as well as wineries, eateries, and locally owned boutiques and antique stores. For a taste of arts and history, visit spots such as Litchfield Historical Society, Milton Historic District, and Topsmead Cottage Tours. The White Memorial Conservation Center houses over 4,000 acres of scenic landscapes, including 35 miles of trails for hiking, fishing locations, and campgrounds. There is always something going on in terms of events and festivals, including the annual Cars for Kids Automobile Show, the Litchfield Arts Festival, and Summerfest.
Cornwall
Cornwall is a picturesque small town nestled in the foothills of the Berkshire Mountains, boasting a breathtaking collection of lush green steep hills, deep valleys, and forested areas. The Cornwall Covered Bridge, built in 1864, is the main attraction, earning a spot on the National Register of Historic Places and dubbing Cornwall the "Home of the Covered Bridge." In fall, the town is especially charming, as changing leaves bring color and warmth, while chilly temperatures ensure everyone is wrapped up and cozy, surely with a hot chocolate in hand. Cornwall offers plenty to do in the great outdoors, including winter skiing down Mohawk Mountain, fly-fishing in the Housatonic and Farmington Rivers, and electric bike rentals for perusing around town.
Mystic
The town of Mystic is a classic New England village home to the gorgeous Mystic Seaport, which features a collection of 19th-century historic watercrafts, alongside views of and access to Long Island Sound. After a day well spent on the water, enjoy an afternoon perusing the downtown area, full of unique spots such as Mystic Knotwork, Mystic Seaport Museum, and Red 36. Other things to do include Mystic Boat Adventures and Cruises, a number of wineries and distilleries, and great pizza spots. Visitors enjoy touring historic spots and landmarks scattered throughout the town, such as Mystic River Bascule Bridge, Olde Mistick Village, as well as the serene nature trails of Denison Pequotsepos Nature Center.
New Haven
Home to the Ivy League school Yale University, founded in 1701, New Haven is an exciting college city and cultural capital with a constant rotation of events, including sports games, concerts, theater shows, and more. First up on the to-do list is a tour of the campus of Yale University itself, featuring 18th-century architecture, as well as Yale’s Art Gallery, the Peabody Museum of Natural History, and the Center for British Art. The city's charm does not end within the borders of Yale. Pay a visit to Chapel Historic District and wander the welcoming streets, touring through the locally-owned boutiques and galleries. Catch a show at the Shubert Theater or the Tony Award-winning Long Wharf Theatre or stop by the Knights of Columbus Museum to delve into the rich history of the area. Do not forget to stop by Little Italy and grab a taste of some scrumptious cuisine before heading home.
Enjoy a Trip to Connecticut
The small towns of Connecticut each house rich histories, maritime adventure, friendly atmospheres and exciting main streets, all of which you can experience in a jam-packed three-day weekend. That said, a leisurely trip relaxing shoreside is also an option, so there is something intriguing for everyone in the Nutmeg State. Whether you choose to explore the gorgeous Yale campus, indulge your inner foodie, or see all the fall colors on a scenic drive, a trip to Connecticut is one to remember.
