Carey Ross (AGI17) Studied the Great Books at St. John’s Before Launching a New Chapter on the Chesapeake Bay
By Meliha Anthony (A25)
Whether studying the Great Books, teaching yoga, raising two toddlers, or leading communications for Chesapeake Region Accessible Boating (CRAB), Carey Ross (AGI17) routinely pursues work with a greater purpose, resulting in a correspondingly fulfilling life.

CRAB is an Annapolis-based nonprofit organization offering sailing and wellness programs to people with disabilities including cerebral palsy, Down syndrome, muscular dystrophy, deafness, and blindness. Its fully accessible waterfront facilities on Back Creek, a tributary of the Severn River, allow them to participate fully and confidently in the region’s most famous sport.
Founded 30 years ago, CRAB’s mission, as stated online, is to provide “the therapeutic benefits of sailing to people with disabilities, recovering warriors, and youth from underserved communities.” CRAB has grown significantly in recent years, says Ross, who came aboard herself in January 2025, and it now offers additional services and activities including fishing, art, and yoga programs.
Before joining CRAB, Ross taught high school English for eight years at St. Mary’s High School in Annapolis. She completed a degree at the St. John’s Graduate Institute in 2017 while working full-time, and she later earned her certification to teach yoga. Her St. John’s education informed these endeavors along the way: While working at St. Mary’s and concurrently studying the Great Books, Ross says, “the pedagogy was phenomenal because I was able to bring that into the classroom. As for [working in] communications, it has been invaluable for me.”
The practice of asking questions to gain a better understanding of the world is deeply ingrained in Ross. “That whole mentality has shaped the way I work, shaped the way I live, and that’s all St. John’s,” Ross says. “It’s always about the ‘why,’ right? Like you want to know why this is happening or why you’re doing something.” That mindset is alive and well at CRAB, where Ross loves both the mission and the people. She recounts seeing the same faces coming in each week and forming relationships with them.
“One thing I will say about CRAB is that they are a very tight-knit community,” Ross says, emphasizing how the staff and volunteers “welcomed her with open arms” from the beginning. “I think there’s really something to be said for that, because it can be really hard to find your footing in a new place, and that just has not been an issue here.” They also embrace local landlubbers, engaging in festivities like the Annapolis St. Patrick’s Day parade earlier this year. “My four-year-old son got to participate, so he got to dress up as a leprechaun,” Ross says, laughing about how her son’s endless energy and excitement persisted long after the parade finished.
New opportunities on the horizon for CRAB include solidifying partnerships with nonprofits that share a similar mission. Ross is excited to see organizations reaching out to CRAB including the Challenged Athletes Foundation, which works across both the West and East coasts. CRAB’s local events, held throughout the year, are held in collaboration with neighboring organizations such as the Eastport Yacht Club, where CRAB holds the annual CRAB Cup. The Cup is their biggest fundraising event of the year, where CRAB athletes compete against 18 other classes of boats.
“What makes it really special is our athletes with disabilities actually participate,” Ross says. “They get off the boat and they just walk with pride about their accomplishments.” Each year, CRABs hold a shore party after the competition, which brought out over 600 guests last summer despite uncooperative weather. “The thing that was kind of amazing about that is there was a huge thunderstorm, and it didn’t deter anyone from coming,” Ross says. “I think that’s a real testament to our cause, and the people that support us and what we do.”
The 19th annual CRAB Cup will take place on August 16, 2025. The following month, CRAB will host a Special Olympics demonstration—part of a global athletic event for individuals with intellectual disabilities held annually in states across the country and around the world. CRAB currently has at least 36 athletes set to compete, all from Maryland and Virginia.
Ross loves working in a role that allows her to connect with so many people in a meaningful way. “When I was looking for a job, this really spoke to me,” Ross says. “I wanted to make a difference and do good in the world, and this was my place to do that.”
“And, I mean," she adds, looking out over the Chesapeake Bay, "you can’t beat the view!”