A long time ago, four sailors started out from Baxters Boathouse in Hyannis to race their sailboats to Nantucket. That race would be the first of the Figawi Race Weekends, and the beginning of what has become a Cape Cod tradition. Hyannis to Nantucket. Join us for great sailing on Nantucket Sound, great fun and camaraderie on the beautiful island of Nantucket, and memories of being part of a great tradition. The Figawi Race, now with over 250 entrants, has certainly grown into one of the premier sailboat races on the east coast. Hyannisport, Massachusetts

For many years the City of Gloucester Massachusetts has proudly sponsored a large gathering of schooners for two days of racing, celebration and socializing. Gloucester has a long and grand history of schooner racing dating back to the International Fisherman's Races between Gloucester and Lunenburg NS, immortalized though the lens of of Morris Rosenfeld in 1922 with the victory the indomitable Bluenose over the Gertrude L. Thebaud. Taking place in the harbor and nearby waters of America’s oldest seaport, the Gloucester Schooner Festival honors the major role the fishing schooner has played in the heritage of Gloucester and the eastern seaboard. Gloucester Massachusetts

The Marblehead-to-Halifax race is a 360-nautical mile course from Marblehead, Massachusetts, to Halifax, Nova Scotia, and is open to all qualifying yachts in five divisions. Marblehead-to-Halifax Ocean Race is run regularly on alternate years from the Newport Bermuda Race, as one of the pre-eminent ocean races of the North Atlantic.

Since its inception in 1977, the Marion-Bermuda Race has been a Corinthian event, and yachts are accepted by invitation. The spirit of the race is that all yachts and crew are participating for the joy and pleasure of sailing, competition, and the camaraderie that accompanies such an off-shore event. The race provides an opportunity for cruising yachts and amateur crews to participate in an ocean race and a rendezvous in Bermuda. It encourages the development of blue water sailing skills on seaworthy yachts that can be handled safely offshore with limited crew. Marion, Massachusetts

Nantucket Race Week is nine days of regattas, awards ceremonies, and parties hosted by Nantucket Yacht Club and Great Harbor Yacht Club to benefit Nantucket Community Sailing. Race Week is the largest fundraiser for Nantucket Community Sailing, and supports youth sailing for island children. Nantucket, Massachusetts

Edgartown Yacht Club held its first race around Martha's Vineyard Island in the summer of 1938, and except for the years of the Second World War the race has been an annual event since then. For a number of years the course was extended to round the Buzzards Bay Tower, but today the traditional tight course around Martha's Vineyard Island is used. Massachusetts

This Race, in memory of internationally known naval architect, Samuel S. Crocker, has been held every summer off the coast of Manchester, Massachusetts, since 1966. Whether young or old, experienced racer or beginner, wood or fiberglass, big or small, please join us for a fun day of racing and socializing with fellow sailors! Here's to sunny skies and fair winds!

The Vineyard Cup Regatta will be held on the waters of Nantucket Sound and Vineyard Sound off of the Island of Martha's Vineyard, Massachusetts. For vessels 22 feet in length and greater. Sail Martha's Vineyard is expecting over 100 sailboats of all descriptions, designs and ages from schooners to catboats to modern design racers. Each day after racing there will be parties for skippers, crews, family and friends with food, drink and entertainment in the Race Village on Beach Road Extension down by the Black Dog Tavern.