Rich in history and natural beauty, Connecticut is a fantastic destination for an unforgettable Memorial Day weekend getaway. Whether you want to play Revolutionary War-era games by the sea or soak up the pastoral glory of the Berkshires, this tiny state has plenty to offer. This region in New England boasts gorgeous Connecticut vacation rentals and a wealth of activities, so you can welcome the summer season with a bang.
Connecticut’s capital city buzzes with energy on Memorial Day weekend. If your vacation rental is in the western part of the city, check out the parade in West Hartford, a local tradition since the 1920s. Another large parade happens in Wethersfield to the south, starting in Old Wethersfield. Later in the day, head to the Webb-Deane-Stevens Museum to wander through a recreation of a Revolutionary War camp. Throughout the day, actors reenact historical battles, hold sword fights, ride horses, and fire muskets.
The Connecticut coast often experiences heavy traffic on Memorial Day weekend; escape the crowds by heading inland to Kent, a stunning town on the western side of the state. Revel in the serenity and the early-summer sun by strolling along the Housatonic River, hiking through the peaceful Pond Mountain Natural Area or climbing next to a waterfall in Kent Falls State Park. In the evenings, chill out in Kent’s charming downtown; local hot spots include the Kingsley Tavern and the Swyft Restaurant.
Car lovers descend upon Lakeville each Memorial Day weekend for the Royals’ Garage Sunday Car Show. This fun festival brings a huge collection of classic cars, motorcycles, race cars, and muscle cars to Lime Rock Park in a celebration of all things automotive. Explore the vehicles on display, chat with the owners, and enjoy food from onsite vendors. The weekend also features a series of thrilling races as part of the Pirelli World Challenge; pack a blanket and arrive early to grab a spot on the grass.
4. New London
Enjoy Memorial Day with a historic twist in New London, the home to Fort Trumbull. The fort, which has been standing since Colonial times, opens to visitors on the holiday weekend, showing off its spectacular ramparts and views of the tall ships in the New London harbor. Inside, restored rooms show how the fort looked at different periods. Be sure to stick around for the annual concert with the local United States Coast Guard band, which is free and kid-friendly.
If one of your summer goals is to get in shape, kick off the season in Bridgeport with the Aquarion Barnum Festival Road Race. This fun event features a fast, flat 5K and 10K race, so you can select a comfortable distance. The race starts and finishes on the Harbor Yard baseball field; stick around afterward for a kids’ fun run and live music at the post-race party. Later, enjoy the lovely late-May sunshine at the nearby Silver Sands State Park, which features beautiful beaches and a long boardwalk.
Put a nautical twist on your Memorial Day at Mystic Seaport, the largest maritime museum in the United States. Inspired by historical celebrations, the museum’s annual Salute to Summer includes once-in-a-lifetime activities such as harpoon throwing and whaleboat rowing. Rent rowboats from the dock and paddle the Mystic River, or take a ride on the sailboat Breck Marshall. On Memorial Day, the museum pays tribute to Civil War soldiers with traditional Decoration Day activities.
If you’re traveling with adults, head to Foxwoods Resort Casino in Ledyard the day before Memorial Day for the first Liquid Sunday party of the year. Put on your best pool gear for this 21+ event, which features a DJ, dancing, and celebrity guests. Come in the afternoon for swimming and relaxing, and stay for dancing late into the evening. Once you’re done in the pool, head to the nearby Mashantucket Pequot Museum’s opening weekend, or book a tee time at the expansive Lake of Isles North Golf Course.
Bring the whole family to Norwich for the annual Memorial Day Norwich Rotary Carnival. Each year, Howard T. Brown Memorial Park comes to life with a midway, carnival rides, and kid-friendly entertainment. Live music and food vendors complete the celebration, which lasts for four days; be sure to pop in after dark to see the lights reflecting off of the Thames River. On Monday, take a break from the carnival to watch the Memorial Day parade and honor fallen veterans at the annual ceremony at Chelsea Parade.
9. Old Saybrook
Plan a Memorial Day filled with fresh sea breezes in Old Saybrook, a gorgeous coastal village near the Connecticut-Rhode Island border. Plan ahead to snag a vacation rental on the ocean, and take advantage of the warm late-May weather with lazy beach days. Head to Rocky Neck State Park to try crabbing, spot rare sea birds, and watch the trains that pass over the park bridge. Both Islander Sport Fishing Charters and Kingfisher Fishing Charters are running at full steam by late May, so you can enjoy angling on the open seas. On Memorial Day, head downtown to watch the Dockside Naval Ceremony and the annual parade honoring American veterans.
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