There are regular summer weekends, and then there are summer weekends spent along the waterfront. Across the East Coast, the season’s calendar is filled with regattas, wooden boat shows, surf contests, and maritime festivals that celebrate life on the water in more ways than one. Whether you’re there to watch impeccably restored sailboats glide through the harbor, cheer on surfers catching the perfect wave, or simply soak up the carefree atmosphere, these are the events worth planning a getaway around this summer.
The Rell Sunn Surf Contest
July 11, 2026
Named in honor of legendary surfer Rell Sunn, this beloved competition celebrates the community-driven side of surfing. Expect talented longboarders, laid-back beach energy, and an atmosphere that feels refreshingly authentic. Held on one of the Hamptons’ most well-known beaches, it’s less about spectacle and more about embracing the sport, camaraderie, and appeal of a day spent in the waves.
The Eggemoggin Reach Regatta
August 1, 2026
Often described as one of the most beautiful wooden boat races, the Eggemoggin Reach Regatta is the embodiment of a coastal New England summer. Classic wooden yachts gliding through the waters of Penobscot Bay create a scene that feels like it’s been taken straight out of a vintage sailing photo. It is understated, historic, and undeniably elegant.
The Queen’s Cup Regatta
August 3, 2026
A sailing tradition, the Queen’s Cup Regatta brings together high-ranking racers and waterfront spectators for an ideal day that has been a long-standing tradition and is rich in history. Being one of the New York Yacht Club’s most prestigious events with a notable list of winners, you won’t want to miss this. Whether you’re watching colorful spinnakers race through the water or enjoying the festivities ashore, this event offers a glimpse into one of sailing’s most enticing pastimes.
The Maine Boat Show
August 7-9, 2026
Set against the postcard-worthy backdrop of Rockland Harbor, this coastal gathering blends beautifully crafted boats with Maine’s celebrated design, food, and culture. Between gleaming yachts, handcrafted wooden vessels, and waterfront shopping, it’s an effortlessly chic excuse for a summer weekend getaway to the water.
Jetfest 2026
August 15, 2026
For those who prefer adrenaline over a leisurely sail, Jetfest delivers a high-speed environment on the water with freestyle jet ski competitions, racing, and stunts. This energy is infectious, making this event a fun contrast to the East Coast’s more traditional boating events. Jetfest is a testament that watersports can be just as thrilling as they are stylish.
The NY Jetski Showdown
August 30–31, 2026
If high-speed watersports are your style, the NY Jetski Showdown is a weekend worth adding to your calendar. Held along the Hudson River at Coxsackie Riverside Park, this two-day event brings together a large community of motorsports enthusiasts through activities ranging from freestyle performances to competitive racing. This is an exciting destination for anyone looking to experience the faster side of life on the water this summer.
The Fishers Island Round Island Race
September 5, 2026
As summer begins to wind down, this iconic race around Fishers Island offers one last celebration of the sailing season. Competitive sailors navigate the island’s scenic coastline while spectators enjoy the gorgeous ocean views and a quintessentially New England atmosphere. This is the perfect finale to a summer spent on the water.
