Jolly Dolphin is a wooden sailing vessel modeled on early Chesapeake Bay oyster dredgers. Referred to as a "three sail bateau," or "two-masted skipjack," it is a successor to the bugeye. Jolly Dolphin was built for a Delaware family for recreational use by James B. Richardson on LeCompte Creek, Maryland in 1958. From 1964 until 2007 she passed through the hands of a half dozen owners, and was abandoned ashore in 2004. Restored with the help of the Richardson Maritime Museum from 2007 to 2010, privately owned and maintained Jolly Dolphin has provided traditional sailing experiences for community outreach. Over the years Jolly Dolphin's passengers have including middle school and high school STEM students, conservationists and Maryland history enthusiasts. She is currently berthed on the Magothy River.

Jolly Dolphin is proud to be sailing this year on behalf of the Magothy River Association, an organization that supports conservation and education on her home waterway. Magothy River Association works for the preservation and improvement of the water quality, plants, and wildlife of the Magothy River and its watershed. The organization's efforts include a comprehensive oyster program that includes an oyster nursery, reef restoration, and a dive program to monitor oyster populations.