The EWE Spirit Cup is May 18.

Sailing for the EWE Spirit Cup

Join EWE Spirit for a fun pursuit-style race in Annapolis on May 18. Once again, the EWE Spirit Foundation, which honors the legacy of Annapolis pro sailor Geoff Ewenson, will be supported by the Sailing Club of the Chesapeake's Spring Regatta and the race for the EWE Spirit Cup.

EWE Spirit Cup sailboat racing
Light air for the 2023 EWE Spirit Cup. Photo by Ted Morgan

The race will take place on Saturday, May 18 and is open to any sailing vessel. Anyone looking to Sail Like EWE and live like EWE should register to sail, fundraise, and join in the post-racing fun!

Make an impact with fundraising

Last year sailors raised more than $35,000, and the EWE Spirit Foundation hopes to make an even bigger impact this year. All sailors and friends of EWE are encouraged to create a peer-to-peer fundraising page. This fundraiser will be held in conjunction with the regatta to benefit the EWE Spirit Foundation. Awards will be given for top individual and top team fundraisers for some off-the-water competition.

The most fun regatta

After racing, enjoy a “Vans and Stepping Out Shirts” party at Horn Point Marina in Annapolis, which will be open to competitors as well as friends of EWE. Geoff Ewenson (in whose memory the foundation was formed) loved having fun regatta shirts, and Vans were his go-to shoes. Sailors and friends will be decked out for the party, so join the fun. 

EWE Spirit Cup Vans and Stepping Out Shirts party
Doug Stryker sporting an epic Stepping Out shirt at the EWE Spirit Cup in 2023. Photo by Ginevra Iliff

Find EWE Spirit Cup registration and fundraising information at

The EWE Spirit Foundation’s mission is to honor the legacy of Geoff Ewenson by helping those facing immediate hardship bridge financial and social support gaps through mentorship, outreach, and financial assistance, thus creating a kind world where everyone has the resources and opportunity to live with dignity, hope, and joy. Since its inception three and a half years ago, the foundation has donated nearly $400,000 to community causes. Learn more at

Learn more about the Sailing Club of the Chesapeake.