Around Long Island Regatta (ALIR)
The Around Long Island Regatta, first run in 1977, covers a 205 nautical mile course combining ocean, harbor and open sound racing. The race’s 10+ divisions include sailboats 24 feet or longer and sailors at all levels who typically finish in one to three days. This unique race is for everyone – weekend cruisers, serious blue-water competitors, double-handers, academy sailing teams, even junior sailors.
Race starts at the end of July.
Full description can be found at https://alir.org
Western District (WD)
The Western District Regatta is a Junior Sailing regatta. Sailors ages 12-17 gather from the western part of the Sound to compete. It is a qualifier for JSA of LIS Champs in the ILCA (all rigs), Club 420 and RS Feva.
The top three finishers in each class are awarded trophies. Everyone has fun!
The race is scheduled for the beginning of July.
Register through JSA of LIS https://jsalis.org/calendar
Heritage Cup
This regatta is part of the very prestigious Classic Yacht Challenge Series. The Heritage Cup has classes for: (https://www.classicyachts.org/ratings/divisions/
- Vintage
- Classic
- Modern Classic
- Spirit of Tradition
- Contemporary
- Good Old Boat
The Haustblót Shorthanded Regatta (or HSR)
The Haustblót Shorthanded Regatta (or HSR) was founded in 2025 by Sea Cliff Yacht Club member and shorthanded ocean sailor Josh Reisberg to celebrate the unique challenge and camaraderie of racing with minimal crew. Inspired by the Norse autumn tradition marking the turning of the seasons, the event brings together solo sailors, doublehanded teams, and “PlusOne” crews for a demanding Long Island Sound course designed to test seamanship, navigation, and shorthanded sail handling.
With distances ranging from 10 to 60 nautical miles based on conditions, the race emphasizes real decision-making and constant crew work rather than simple point-to-point sailing. Created to promote greater interest, competition, and participation in shorthanded sailing, the HSR serves both as a proving ground for experienced sailors and a welcoming gateway for those looking to enter the fast-growing world of shorthanded racing.
The day concludes ashore with food, beer, and sea stories as sailor’s trade lessons learned and celebrate the craft that prepares them for even bigger offshore challenges.
Frostbiting
Throughout the winter season, we host an exciting series of Frostbiting events for ILCA and Sunfish. Beginning in November, we sail every Sunday afternoon until the first Sunday of May. We emphasize fun and camaraderie with informal races. All levels are welcome.
Sunday afternoon (weather permitting) November through May.
Frostbiting