The Schooner Eleanor , launched in May 1999, was built in Kennebunkport by Captain Rich Woodman and a crew of local craftsmen to the lines of L. Francis Herreshoff’s 1935 Mobjack design. Although her hull was constructed using modern techniques, the Eleanor is in every other way a traditional gaff-rigged schooner. Spruce spars, mahogany transom, locust rails and hand carved trail boards all contribute to the beauty of this vessel. Flying four sails with a large teak cockpit and spacious cushioned cabin tops to stretch out on, the Eleanor will give you the feel of yachting in the 1930s. Captain Rich shares his grandfather’s passion for boatbuilding and carries on this tradition in the off-season by restoring and building custom wooden boats at his boat shop in Kennebunk. He has also taught wooden boat construction at the Landing School.

Schooner Eleanor is raising funds for the Landing School of Boatbuilding and Design in Arundel, Maine. The Landing School is a leader in boatbuilding and design and has prepared graduates for a wide range of positions in the marine industry since 1978. Students build skills and knowledge through a combination of innovative classroom instruction, faculty mentorship, engagement with industry leaders, and project work. The Landing School offers eight-month diplomas in Wooden Boatbuilding, Composite Boatbuilding, Marine Systems, Yacht Design, and Boatyard Management, as well as a two-year associate degree. Students from around the world come to The Landing School from diverse personal and professional backgrounds and each class includes recent high school and college graduates, career changers, veterans, and retirees.

Welcome to the 2025 Virtual Great Chesapeake Bay Schooner Race!

While normal sailboat racing happens on the water, this race is completely online. Each participating schooner has teamed up with a nonprofit partner, and is racing to raise as much money as possible for their charity. YOU can participate in the race by choosing a schooner, making a contribution, and sharing this webpage with your family and friends!  90% of gifts will go directly to the charity of your choice. The other 10% will help the Great Chesapeake Bay Schooner Race achieve its mission to promote awareness of the Chesapeake Bay’s heritage; to encourage preservation of the Bay’s resources; to support Chesapeake Bay education and clean-up efforts; to bring historic schooners to the Bay; and to encourage schooner sailing and preservation. 

Please take a moment to learn more about our schooners and the organizations they support. At the start of the race, please come back here to make a donation and support your team!

Donation links will be available from 12:00 noon on Wednesday, August 13 through 3:00 PM on Saturday, August 16. 

Thank you for supporting our schooner community!

Please note:  GCBSR will only share your contact information with the charity you donated to.