Read the 2026 Hospice Cup Sustainability Report
Hospice Cup is continuing to strengthen its sustainability efforts in 2026 through expanded education, new initiatives, and a continued focus on reducing waste and protecting the Chesapeake Bay. As part of a growing community of clean regattas around the world, we’re committed to doing our part to eliminate single-use plastic, reduce our environmental impact, and […]
Hospice Charities Win at at 45th Anniversary Hospice Cup Regatta
ANNAPOLIS, MD – Sailors from across the Chesapeake and beyond gathered on Saturday, September 19, for the 45th annual Hospice Cup regatta, bringing together competitive sailing, community and philanthropy in support of non-profit hospice care. The regatta, hosted by the Storm Trysail Club, Severn Sailing Association, and West River Sailing Club, fielded sailors from half […]
Bill Sutton Named Winner of This Year’s Hospice Cup Art Competition and 2026 Artist in Residence
Hospice Cup is pleased to announce Annapolis artist Bill Sutton as the winner of the 2026 Hospice Cup Art Competition with his painting Windward Douse. Sutton will also serve as the event’s 2026 Artist in Residence. Presented in partnership with the Maryland Federation of Art, the annual Hospice Cup Art Competition highlights exceptional regional artists while supporting […]
Winter 2026 Newsletter
Join Us for Winter’s Watch at the Inn at Perry Cabin in St. Michaels There are only a few tickets left for this farm-to-table dining experience on the Eastern Shore. When: Saturday, February 28th at 5:00 PMWhere: Inn at Perry Cabin, St. Michaels – 308 Watkins Ln, St Michaels, MD 21663 Click here to secure your tickets. We’ve missed sailing […]
Read the 2025 Hospice Cup Sustainability Report
In 2024, Hospice Cup earned its first ever platinum clean regatta certification from Oceana’s Sailors for the Sea. The prestigious certification from sustainable boating’s recognized governing body capped a year of dramatic progress: zero-waste efforts, a volunteer-powered Green Team, locally sourced food and composting strategies, and the elimination of single-use plastics across both land and […]
Eye On Annapolis: Annapolis Sailors Raise More Than $550,000 as Tradecraft Team Wins 2025 Triple Crown of Charity Sailing Trophy
The 2025 Triple Crown of Charity Sailing Trophy has been awarded to the Tradecraft Team, led by Roger Mason and Chris Valentino, after a record-setting season of racing and fundraising that showcased both competition and generosity on the Chesapeake Bay. Tradecraft Team Takes 2025 Triple Crown Title The trophy presentation and reception were held October […]
SAIL-WORLD: Triple Crown of Charity Sailing Trophy 2025 winner announced
The highly anticipated 2025 Triple Crown of Charity Sailing Trophy presentation and reception was held at the Chesapeake Region Accessible Boating Annapolis Adaptive Boating Center on October 30th. The leadership of Maryland Cures Cancer Regatta, the CRAB Cup, Hospice Cup, and Weems & Plath were present to celebrate the awarding of the trophy to Roger […]
Fall 2025 Newsletter
Record scratch sheet & fundraising at the 2025 Hospice Cup Racers hoisted their sails last month for the 44th annual Hospice Cup regatta, with 99 registered boats and more than $231,000 raised for non-profit hospice organizations. Click here to read all about this year’s race and shore party. Missed the Shore Party and want to pick up […]
Spinsheet: Hospice Cup 2025 – Fun, Joyful, and Inviting
Read all about the 2025 Hospice Cup in the October issue of Spinsheet!
Hospice Cup Celebrates 44 years on the Chesapeake Bay with Record Scratch Sheet and Non-Profit Fundraising
Annapolis, MD – Local yacht racers hoisted their sails on Saturday, September 13th for the 44th annual Hospice Cup regatta, an annual charity dedicated to raising funds and awareness for non-profit hospice organizations. The Sailing Club of the Chesapeake, who hosts the event, partnered with Storm Trysail Club and Severn Sailing Association to manage three […]
