Scholarships
One of the foundation's biggest accomplishments is the annual scholarship program for young college bound students. Recipients are selected based on character - specifically how they treat other people, what others say about them, and being of good character - all of which reflect Olivia herself. We have awarded 120 scholarships to date.
The scholarship program began in 2012 with a single award - all the foundation could afford in its first year - and has grown steadily ever since, some years receiving close to 100 applications. The program has also evolved to support students across multiple years of their college journey, with several recipients receiving awards more than once, reflecting the foundation's belief that character-driven young people deserve sustained support, not just a single moment of recognition. Every scholarship is a direct expression of who Olivia was, a young woman who made everyone around her feel seen, valued, and cared for, and every recipient carries that spirit forward into their studies, their communities, and their lives.
Our Past Programs
Grants
Beyond its school grants, the Olivia Constants Foundation has directed its community giving toward the people and organizations that need it most. Through the Anne Arundel County Partnership for Children, Youth and Families, OCF supported mothers transition their families to a stable environment, while also helping other families afford essentials like a new AC unit, clothing for children, and kitchen supplies. The foundation was also a consistent supporter of Food Link Maryland and Walk the Walk Foundation.
The foundation also extended its reach through hands-on volunteerism, helping package thousands of meals at Feeding Northeast Florida, and maintained an ongoing partnership with the Downtown Sailing Center in Baltimore to keep sailing accessible to youth and persons with disabilities. Closer to home, OCF provided direct support to the Broadneck High School Sailing Team in honor of Olivia's love for the sport. In every case, the giving reflects the same guiding question the board has always asked: what would Olivia do?
School Grants
Over the years, the OCF awarded 27 grants to Anne Arundel County Public Schools, funding programs like GirlTalk and the Kindness Club - initiatives that give young people a safe space to discover who they are, build confidence, and learn how to show up for one another. It was exactly the kind of investment Olivia would have believed in. A major focus of the school grants was funding programs centered on kindness and positive student culture.
The grants covered a wide range of classroom needs, particularly for under-resourced schools. The consistent thread was equipping teachers with tools they couldn't otherwise afford, putting real resources directly in front of students.
In short, the OCF's school grant program reached dozens of schools across Anne Arundel County, funding everything from iPads to kindness clubs, and helping build a more inclusive, empathetic school system in Olivia's name.
Anti-Bullying Through the Arts Contest
The "Creating Change Through the Arts" contest gave students across Anne Arundel County Public Schools the opportunity to communicate a message to their peers about what is important to them - about bringing each other together and fostering an inclusive environment in their schools. It builds directly on the OCF's broader grant programs and anti-bullying efforts within the AACPS.
This program turned student creativity into a powerful tool for change - giving young people a voice, a prize, a charity to support, and artwork displayed in hallways across Anne Arundel County, all in service of making schools kinder places. The program carries particular personal meaning because Olivia herself was affected by bullying, which is why combating it became one of the foundation's core missions.
Olivia's Team Racing Invitational
The OTRI was designed to represent the way Olivia would have liked a sailing event to be - lots of fun, with some racing in between. It is one of the most unique team racing regattas in the sport. There are no structured teams; instead, each skipper/crew pair is randomly placed on a different team for every single race, in a 2-versus-2 format on day one and a more traditional 3-versus-3 format on day two. By drawing boats from the top, middle, and bottom tiers to create balanced teams, racing is exciting and fair and everyone had the chance to meet as many new sailors as possible.
In short, the OTRI is far more than a regatta. It's an annual gathering that embodies everything Olivia stood for - connection, kindness, and joy - while raising money, earning national recognition, and leaving a permanent legacy in the sailing community.
National Recognition
In 2014, the OTRI was awarded the prestigious St. Petersburg Trophy by U.S. Sailing for excellence in race management - one of the sport's most respected honors, affirming that the event had made a meaningful mark on competitive sailing nationally.
A Perpetual Legacy
The OTRI now has a perpetual trophy, as does the "Spirit of Olivia" award - given annually to a junior sailor who exhibited the qualities Olivia held dear. These trophies ensure that Olivia's name and values are permanently woven into the fabric of the Annapolis sailing community.