From a Small Start to Big Finishes

America’s largest charity regatta in numbers and dollars, Hospice Cup began in 1981 as an informal race among a small group of people interested in sailing and hospice care. Netting almost $28,000, the first Cup was amazingly successful—and fun! About 35 sailboats raced from Annapolis to St. Michaels on the Eastern Shore of Maryland. A few private power yachts carried sponsors and guests as spectators. All celebrated the occasion at a post-race party at a waterfront home, where trophies were awarded.

To repeat the success and fun, the founders formed Hospice Cup Inc., an all-volunteer organizing group independent of the benefiting hospices or racing groups. They also recruited a local sailing club to dedicate an existing race on the crowded local schedule to the cause.

Scheduling the race as part of the regular racing season attracted many more sailors, while the organizing board continued to spread the word and attract more sponsorships and hospices. Racing continued from Annapolis to St. Michael’s for several years, then shifted to racing around buoys in the Bay, with everyone adjourning to a noteworthy party on the shore.


There are many ways to get involved! Are you a sailor? Race in the event! Want to make an impact, volunteer for the shore party! Can’t make the event? Donate!

We need you in any capacity you can give, and we are so grateful for your support!