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About

Our History

The Hospice Cup regatta was founded in 1981 as a 501(c)3 non-profit organization with the goal of raising awareness and funds for hospice and palliative care in our region.

What began as a small local race in America’s sailing capital has evolved into a premier event, with more than 100 boats and nearly 1,000 sailors coming together annually from across the country. Today, this beloved Annapolis race is the largest charity regatta in the United States and a destination for competitive racers.

For more than 40 years, Hospice Cup has continually supported local care programs in our region, including Montgomery & Prince George’s Hospice, Talbot Hospice, Capital Caring Kids, and the Luminis Health Gilchrist Lifecare Institute at Anne Arundel Medical Center.

The non-profit hospice programs that the Cup supports offer compassion, dignity, and a dedication to quality of life for those in our community facing the challenges of serious illness and end-of-life. This includes comfort care for loved ones as well as bereavement and family services not often covered by insurance or medicare.

Leadership

John Richard

Board President

Get To Know John

Rick Chubb

Board Member

Get To Know Rick

Brien Jones-Lantzy

Board Member

Get To Know Brien

Mariah Leffingwell

Board Vice President

Get To Know Mariah

Ken Manning

Board MembeR Ex Officio

Get To Know Ken

David Mencarini

Board Treasurer

Get To Know David

Matt Sheridan

Board Member

Get To Know Matt

Jen Simmons

Board Member

Get To Know Jen

Caitlin Whately

Board Secretary

Get To Know Caitlin

About Hospice & Palliative Care

Hospice is specialized healthcare for those contending with advanced terminal illness. It offers comprehensive comfort care for patients and families, with special attention to medical, physical, and mental health and an important focus on quality of life.

At a time when patients are faced with limited options, hospice provides those with serious illness the gift of choosing how and where they want to spend their time.

95% of hospice patients receive in-home care lasting an average of 10 days. Hospice care programming can cost up to $1,500 per day per patient, which is why it’s so important that we fundraise to support local care centers that are working hard to make life better for those in our community who are struggling with terminal ailments.

The belief that everyone deserves compassion, dignity, comfort, and choice is central to our mission. That’s why we partner with organizations that enable access to care choices, including relief from the symptoms of serious illness for under and uninsured patients.

Congratulations to 2025 winner Leah Bell
for her artwork Racing Rhythms.

Hospice Cup Artist Selection

The Hospice Cup Artist Selection has a storied history dating back almost as long as the Cup itself.  Each year, Hospice Cup partners with the Maryland Federation of Art to host a competition of local artists.

The winning work and artist are honored at an annual spring reception that is open to the community, and the selected image serves as the feature artwork for that year’s regatta. For more information and to sign up for news and alerts about the next artist competition, signup for our email list here.

The 2025 winner and this year’s Hospice Cup Artist in Residence is Leah Bell, who won with her oil painting Racing Rhythms.

A Focus on Sustainability

Hospice Cup is a registered Clean Regatta, achieving its platinum certification in 2024.

This event is lucky to call the Chesapeake Bay watershed home, so we place a high priority on care and stewardship of local environment and wildlife. We are partnering with sponsors, businesses, and organizations who share this commitment to protecting local shorelines and minimizing waste. With their help, this year’s skippers bags and regatta giveaways will include a variety of premium reusable, practical, and upcycled goods. Skippers should encourage their crews to avoid single-use plastic bottles and instead bring reusable water bottles to this year’s race.

Crew meals are available for pre-order from our Bread & Butter Kitchen, and feature locally-sourced food, including vegan and vegetarian options. Dinner and beverage service at this year’s shore party will utilize only compostable and reusable materials.

Read Our Sustainability Report

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P.O. Box 1443, Annapolis, MD 21404

Hospice Cup, Inc is a 501(c)(3) nonprofit organization dedicated to raising funds for and awareness of hospice care in our region.

Helpful Links

Hospice Cup, Inc. is a proud member of the National Hospice Regatta Alliance.

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John is an avid sailor and serves as the fleet liaison for the Hospice Cup.

You can typically find John out on the water with the Annapolis Sailing School, racing on Wednesday nights, or crewing on the Historic Skipjack Wilma Lee. While on land, John spends time with his daughter and serves the flexible packaging industry as a lobbyist.

My Background – I dedicated 8.5 years to the US Navy, serving as a Nuclear Reactor Operator on multiple aircraft carriers. After my tenure, I transitioned to the semiconductor industry, where I am currently advancing my career.

What made you want to get involved with Hospice Cup? – I have been familiar with Hospice Cup for many years and have witnessed the significant role it plays in raising essential funds. However, it was not until a couple of years ago, when my older brother required Hospice services, that I truly understood the profound impact of their assistance. Their support enables families to focus on being present with their loved ones, while effectively alleviating the associated stress through meticulous coordination of care.

Favorite Vacation Spot – I’ve been soaking up the fun in Chautauqua, NY since I was just two weeks old! Every summer is a blast, filled with amazing friends and unforgettable memories. I can’t wait to see what adventures this year brings!

Brien is a proud member of the Board of Directors of Hospice Cup Inc.

He is an active member of the Annapolis community having lived in this wonderful town for over 31 years.

Of his three Master’s Degrees Mr. Jones-Lantzy holds a Master’s of Wireless Telecommunications from Edinboro University, in Pennsylvania and is presently pursuing his Doctoral degree from John’s Hopkins University. He is a fellow of the Telecommunications Engineering and Management Institute of Canada (TEMIC) and a guest lecturer at the University of Maryland and the United States Naval Academy.

Mariah is an attorney at Clark Hill, where she specializes in data privacy, cybersecurity, and other regulatory matters.

Hailing from Easton, Maryland, she is a seasoned competitive sailor earning college All-American honors two years in a row at St. Mary’s College of Maryland.  She has also taught and coached sailors at Tulane University, Annapolis Yacht Club, Portsmouth Abbey High School, Miles River Yacht Club, and the Tred Avon Yacht Club.

Leffingwell is passionate about giving back to the community and engages in numerous volunteer and service projects that make a positive impact on those in need.

What made you want to get involved with Hospice Cup? – Wonderful care for deceased daughter by Montgomery Hospice.

Favorite Vacation Spot – Amelia Island, Florida… and I live there!

Where could we find you in your free time? – Hiking or on my boat.

What made you want to get involved with Hospice Cup? – I initially got involved with Hospice Cup because a friend’s mother who I knew well was cared for by Hospice of the Chesapeake (HOC). A few years later HOC provided excellent care to my mother-in-law in our home and I was so impressed by the support and guidance given to my wife and I.

Favorite Vacation Spot – The best vacation trip I have ever taken was to Florence, Italy and Paris, France.  Two must-see European cities.

Where could we find you in your free time? – You can generally find me reading a book, listening to music or working outside in my yard.

Matt learned to sail with his family on small lakes in Lancaster, Pennsylania and later on the Sassafras River out of Georgetown, Maryland.   Racing on Lightnings in College.

After a long absence and ten corporate moves, the latest here to Annapolis, he returned to sailing three years ago.  Ultimately logging 110 days on the water in 2024, on Cheshire Cat, a performance catamaran, volunteering on the Skipjack Wilma Lee, and the Annapolis Sailing School Keelboat Club.

As a Financial Services Manager for a Major Car Company, Matt looks forward to spending the maximum amount of time outside and on the water on evenings and weekends.

Finally, Matt looks forward to aiding the good work of Hospice, having witnessed it firsthand in the lives of friends and family members.

Jennifer specializes in content strategy for YouTube, where she focuses on developing and managing the distribution of content across the platform. She is also the owner of a thriving wedding and family photography business.

Jennifer has called Annapolis home for the past 22 years, where she embraces the Chesapeake Bay’s rich maritime culture. She actively participates in sailing events and fundraisers, blending her passion for the water with her commitment to supporting meaningful causes to help support the local community.

Jennifer brings her creative expertise and unique perspective to the board of directors for Hospice Cup. With a strong background in both digital content and community engagement, she works to connect with local supporters, drive awareness and to fundraising efforts that directly benefit the hospice community.

Having witnessed the profound impact hospice care provides—not just for patients but for entire families navigating challenging transitions—Caitlin is committed to bringing together sailors, supporters, and sponsors to create meaningful connections while funding vital care services. She believes strongly that when communities unite, we create ripples of compassion that extend far beyond what any single organization could accomplish alone.

When not engaged in board activities, you’ll likely find her experimenting with new recipes in the kitchen, lost in the pages of a good book, or catching live music. Vacation planning is her not-so-secret talent and she’s been known to organize itineraries that impress some of the best party planners.

At home, Caitlin’s household operates at barely controlled chaos levels with two energetic kids, two Bernadoodles, two guinea pigs, and two fish who have somehow outlived every houseplant she’s ever owned. As her children helpfully point out, she’s much better at remembering to feed things with eyes that stare back at her.

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