Connecticut isn’t just known for its rich history. During Labor Day weekend, this New England state offers a seemingly endless bounty of themed fairs and festivals. Additionally, its many national and state forests, recreational areas, and coastline means there are plenty of exciting things to do and see. Book a stay at a Connecticut vacation rental for your upcoming Labor Day weekend trip. Take a look at the best getaway locations in the state perfect for enjoying a few of the last warm days of the year.
Middlebury is a town in western Connecticut that doesn’t have a lot of urban offerings, but it boasts some great access to nature and fun. Quassy Amusement Park, conveniently located on the shores of Lake Qassapaug, has its annual Carload Labor Day Weekend event. At this event, you and the kids get to enjoy various attractions, including an award-winning roller coaster and a water park that has a beach on the lake. While there, visit Sandy Beach Club for lakefront access, kayaking, and swimming, or stop at the Flander’s Land Trust Whittemore Sanctuary for some hiking. There are about half a dozen hiking trails that thread through the woods around the lake.
Lebanon, in the eastern part of Connecticut, hosts the New England’s Old England Renaissance Faire. Kicking off on Labor Day weekend, the month-long event offers everything from time travelers weekend themes to fantasy and romance weekend themes. You can meet fantasy writers, take part in costume contests, shop at the bazaars, and enjoy the shows, which include jousting, juggling, theater, archery demonstrations, weapons demonstrations, knights school, and falconry shows. Escape the crowds for a while at Mooween State Park and Red Cedar Lake, located in the southern corner of the town’s boundaries. Hike the Red Cedar Lake Trailhead and stop by the neighboring Nat’s Nook Bakery for some sustenance, or rent a kayak or boat and go fishing on the lake.
The annual Woodstock Fair always falls on Labor Day Weekend, with four days of roller coaster and amusement park rides, a go-kart track for racing, live music, tractor pulls, antique exhibits, and a craft area. There’s also plenty of livestock; there are three barns dedicated to cows, sheep, and small animals on-site. There’s also a horse show and food vendors offering pretty much any food could hope for. Woodstock also offers ample outdoor fun at Bigelow Hollow State Park, where you can scuba dive in the Mashapaug Lake or go kayaking among the towering trees.
Westport is located in southern Connecticut along the Long Island Sound. While other cities and towns are celebrating the Labor Day weekend with agricultural fairs, Westport is about the Blues, Views, & BBQ Festival. This festival has activities for kids such as face painting and rides, live music for the adults, and plenty of good barbecue for everyone. In fact, the fair holds a barbecue competition, so you can taste some of the best barbecue in town. Located on the coast, Westport also has waterside vacation rentals where you can relax and enjoy the views. Or, if you don’t have a place on the water, you can head down to Westport Longshore Club Park or Sherwood Island State Park for beach access and a hike through the trees.
5. New London
If you want to lay out on the sand while enjoying the surf on your feet, head to New London, which is home to one of the top beaches in the state: Ocean Beach Park. This beach park has a playground, pool and water slides to keep the children entertained. Hop over to Harkness Memorial State Park for hiking and a tour of the Eolia Mansion. While you’re in New London, go to the Lyman Allyn Art Museum, which offers free admission the first Saturday of every month. Before heading home, head to Fort Trumbull Park, where the U.S. Coast Guard band commemorates the War of 1812 with music and cannon fire.
6. Old Lyme
Old Lyme lies on the mouth of the Connection River and the Long Island Sound. During the Labor Day weekend, the Florence Griswold Museum sponsors a discovery Sundays event in which you can view American impressionist paintings and then learn how to paint at the Education Center, a fun activity for both kids and adults. Next, head to Rocky Neck State Park, where you can enjoy saltwater fishing, swimming, hiking, and picnicking.
Milford’s Silver Sands State Park is one of the top 10 New England beaches. The large swathes of beach put you in a perfect location for swimming, and a long boardwalk follows along the beach with wetland grass and streams on one side and the ocean on the other. Sit on one of the benches along the boardwalk, and enjoy the violet and indigo colors that appear in the sky during sunset. At low tide, you can even walk across to Charles Island. Head over to Walnut Beach for the annual three-day Labor Day weekend concert series, free of charge.
Middlefield’s inland, about midway between Hartford and the Long Island Sound. This small town with only a few thousand residents is perfect if you want to relax during your last summer vacation. Plus, the number of orchards makes it a great place to pick fruit. During Labor Day weekend, enjoy Pear-Apalooza at Lyman Orchards, a fruit festival where you can pick your own pears, enjoy live music, take a horse-drawn wagon ride (or a pony ride for the kids), and join a pie eating contest. On Labor Day, there’s live music and a market where you can grab fresh fruit pastries. Finish off your weekend with a hike to Wadsworth Falls at Wadsworth Falls State Park, a scenic area.
Bolton, just east of Hartford, is a rural town that focuses on its rural roots during Labor Day weekend. The Lutz Children’s Museum does an Annual Farm Day at the Fish Family Farm. The kids can enjoy pony and hay rides, visit the animals, play games, and enjoy live music. Plus, this farm is also a creamery and dairy, so delicious, fresh, homemade ice cream is a must-have. Finish your vacation with a trip to Bolton Notch State Park for some swimming, hiking, or relaxing.
Colebrook lies along the Massachusetts border in the northwestern part of Connecticut. This town, with a population barely over 1,000, hosts the annual Colebrook Fair during Labor Day weekend. The offerings include a cardboard boat regatta, a car show, pony rides, a petting zoo, a pet show, face painting, craft vendors, a flea market, and live entertainment. Kids can also explore a real fire truck. This town includes the Algonquin State Forest, Charles Arnold Recreation Area, and Colebrook River Lake, which offers ample recreational activities. The 2,545-acre Algonquin State Forest is a prime place to hike through the woods and keep an eye out for exotic birds.
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