Schooner Eric Credit

The Great Chesapeake Bay Schooner Race: 30 Years of Racing to Save The Bay

Photo Credit: Eric Moseson


We love working closely with our businesses and being a part of the community. Every now and then, ‘business’ also gets bumped to a whole new level of fun. The Great Chesapeake Bay Schooner Race (GCBSR) is just one example.

What originally began as a bet (over a case of beer) between Captains, Lane Briggs of the Tugantine Norfolk Rebel and Jan Miles of the Pride of Baltimore II has now become an annual event drawing thousands in each year.

While schooner “racing to market” has played a historic role in early trade wars and cargo hauling, this event promotes education around the Chesapeake Bay’s maritime heritage while partnering with other organizations with similar missions like the Chesapeake Bay Foundation, the Waterman’s Museum, and more. GCBSR has been able to donate over $200,000 to organizations like these in Virginia and Maryland so far.

In 2018 the 501c3 expanded their education program by partnering with local schools to get kids out on the water. Fifty students from Portsmouth completed the program last year, and they expect to get over a hundred students out on the water this year in Norfolk and Baltimore.

“We are excited to expand our event to include running educational programs for kids under sail that would not have had this opportunity otherwise.” – Keith Jones, Treasurer, GCBSR

This year marks the 30th anniversary of the race, and its return to Norfolk, scheduled to kick off in Maryland on Tuesday, October 15th. There will be a Parade of Sail around Baltimore’s Inner Harbor, followed by the exciting start of the race, and boats finishing on Friday, October 18th in Norfolk.  The schooners will be docked at Freemason Harbor starting Friday October 18th and continuing through the weekend.


GCBSR is both a deposit and merchant services customer. Credit and debit card processing is usually only needed on their website for donation collection. But when this event comes to town, our Chesapeake Payment Systems team gets to provide terminals onsite for this event in Maryland and Virginia, to support the sales of schooner shirts and other race gear.

Keith said that they previously used PayPal and paper checks to handle these functions, but were limited to one device at a time, and PayPal support wasn’t based locally. He also wanted to upgrade the security of their transactional data for retail sales and online transactions using the organizations new CRM system and insuring full PCI Compliance.


In supporting ‘local businesses,’ we asked Keith what kind of advice he would offer a fellow entrepreneur. Lucky for us, we got a part in that story as well. Prior to Chesapeake Bank, GCBSR was in a relationship with another bank. He made a wish list of things he wanted and needed. The existing bank said ‘no’ to everything that he asked for or charged a fee.

Thankfully, Erin Johnston on our CPS team was also provided with the same list. We were able to accommodate everything he needed. So his advice— “Chesapeake Bank is a bank that you can ask-- can you do this? They will try their darndest to come up with a solution for you. You will work with your bank as closely as your ‘business partner.’ It’s important to find a partner that can grow with you and is sophisticated. So, know what you need and have the conversation(s).”


One of the biggest challenges for any non-profit is attracting and keeping volunteers. For the GCBSR, it’s no different. They can always use extra hands for events, admin, and technology, or your donations for their educational programs. Don’t forget the race is next weekend. So watch the Parade of Sail in Baltimore or walk the docks at Freemason Harbor in Norfolk over the weekend and chat with the schooner crews. You can also monitor the race live with this link.


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