Five May Regattas Sailors Should Sign up for NOW

Posted April 24, 2025

Gather Your Racing Team and Sign up for Excellent Spring Racing

Weeknight racing has started on the Chesapeake and tune-up regattas are unfolding from mid-April through early May, when the first big event of the sailing season, the Helly Hansen Sailing World Series Annapolis comes to town. Then, what’s next for your team?

The Crocodile team at the 2023 Down the Bay Race from Annapolis, Maryland, to Hampton, Virginia, on the Chesapeake Bay. This year's edition is the 75th anniversary! Photo by Will Keyworth

If you’ve not signed up for most of, if not all of these significant May events, why not register now? Of course, there are more events to sign up for—we list them in our calendar. If ever we miss one that’s important to you and your club, send a note to [email protected]. We can’t always fit the smaller events in our print calendar, but we’re happy to include them online.

Here are registration links to five SpinSheet favorites:

May 10—AYC Spring Race to Oxford because who doesn’t love another opportunity to sail to Oxford and party at the Tred Avon Yacht Club?
May 17—5th Annual EWE Spirit Cup because who doesn’t love a pursuit race followed by a party with beer and cake that raises funds for the community? (Oh, there are windward-leewards this year for Harbor 20 and Melges 15 classes). Oh, and there’s La Spirit Beer, brewed by Forward Brewing in honor of EWE Spirit, and handed out after the race. This event holds particular significance for the SpinSheet family, so we hope you will join the on-water fun and fundraising with us.
May 22-24—Down the Bay Race 75th Anniversary because who doesn’t love to sail 120 miles down the Bay to party at Hampton Yacht Club?! Seriously, where is everybody? Are there only 11 boatloads of sailors brave enough to do an overnighter? Or have you guys just been too busy prepping your hulls to sign up for this special anniversary edition of a beloved Chesapeake race? Sign up now!
May 24—Annapolis to Miles River Race because who doesn’t love a chance to sail to St. Michaels and party at the Miles River YC, maybe even head into town and see the sights? The yachtscoring link was off on the MRYC website, so click here.
May 29 - Jun 1—Southern Bay Race Week because who doesn’t love the southern hospitality at Hampton YC and the chance to sail in one of the biggest Chesapeake regattas of the year? If you’ve not yet made it to this event, why not sail in the Down the Bay Race (get some sleep) and then sail in SBRW the next weekend?

Find more great racing events here.