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August 2025
47th Fools’ Rules Regatta
Competitors in this event, sponsored by the Jamestown Yacht Club, must build a “sailboat” from non-marine materials and attempt to sail a 500-yard downwind course. Volunteers are needed!
Find out more »53rd Annual Opera House Cup Regatta
The first all-wooden, single-hulled classic boat regatta on the East Coast, this event is co-hosted by Nantucket Yacht Club and Great Harbor Yacht Club.
Find out more »HYC Mayors’ Cup Regatta
With a pursuit-style start and three rounding marks, this race is quite the fiasco!
Find out more »New England 100
This F18 Americas Championship Warm Up Regatta is organized by the Narragansett Adult Athletic Sailing Association and sailed on Narragansett Bay.
Find out more »F18 Americas Championship
This NAASA F18 League regatta is hosted by Sail Newport in Newport, RI.
Find out more »Herreshoff Classic Yacht Regatta & Newport-to-Bristol Feeder Race
Hosted by the Herreshoff Marine Museum, this event is part of CYOA Classic Yachts Challenge Series.
Find out more »80th Annual Ram Island Yacht Club Invitational Regatta
Our friends at the Ram Island Yacht Club (RIYC) in Noank, CT are holding the club's 80th Annual Invitational Regatta, a race around Fishers Island, on Saturday, August 23. With few interruptions, Ram Island Yacht Club has held this race annually since 1945. RIYC welcomes all registered competitors to this challenging race that has historically drawn as many as 140 boats. For more information including Notice of Race and registration via the Clubspot, visit https://theclubspot.com/regatta/FG1fvHFERa, where party tickets…
Find out more »The Vineyard Race
This Labor Day Weekend classic offers a choice of three courses: 238 nm from Stamford, CT around Buzzards Bay Light Tower and back, 143 nm to Seaflower Reef and back, and 116 nm to Cornfield Point Shoal and back, with divisions for IRC, PHRF, HPR, Multihulls, Classic Yachts and Double-Handed boats and a Corinthian Challenge for college sailors.
Find out more »September 2025
47th Annual Norwalk Seaport Association Oyster Festival
Attractions include a New England Seaport Village, harbor tours, historic and working vessels, arts & crafts, barbecue competition, oyster shucking competition, Pirate’s Coast Adventure, Kids’ Cove, live music, and more.
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