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Deal Island Skipjack Race & Festival – Sept 6–7, 2026 Skipjack Heritage Days – Sandy Point State Park, Annapolis, MD – Sept 12–13, 2026
Choptank Heritage Skipjack Race - Sept 26, 2026, Cambridge, MD Skipjack racing returns to Heritage Days after 35-year hiatus Deal Island Skipjack Races
Deal Island was once the “home port” for a large fleet of skipjacks and continues to be home to several of the remaining vessels still used commercially for oystering on the Chesapeake Bay. Skipjack racing on the Chesapeake Bay dates back even further. Informal races began as early as 1872, when watermen held “shakedown sails” to test their boats before the oyster season—often turning into friendly but competitive, and sometimes wager-based, contests. The first official Skipjack Sailing Workboat Race was held in June 1927, marking the beginning of a long-standing maritime tradition.
The captains, mostly hailing from local communities such as Deal Island, Wenona, Rock Creek–Chance, Dames Quarter, Oriole, Dorchester and one or two other counties represent generations of watermen deeply rooted in the region. For centuries, the economy of the greater Deal Island area has been shaped by life on the water—primarily through crabbing and oystering. Through this site, you’ll gain insight into the history of the skipjacks, as well as the lives of their owners, captains, crews, and families—offering a glimpse into the enduring traditions of the waterman’s way of life.
On our website, you will find the histories not only of skipjacks and other working vessels, but also of the greater Deal Island area and its surrounding communities. It is our honor to preserve and care for this heritage—creating a sanctuary of local culture and tradition. Misc. Skipjack's, Schooners, etc. racing in newspaper article from the Baltimore Sun in 1929. Excellent list of Skipjack's- Credit The Last Skipjack's Project/Cindy Miller
Sandy Point State Park Skipjack Race
Building on a successful inaugural year in 2025, the festival returns to Sandy Point State Park for a two-day celebration of the maritime culture of the Chesapeake Bay and Maryland’s iconic skipjack fleet. Guests will enjoy the rare opportunity to see 15 historic and two traditional buy boats, with public deck tours and free rides aboard historic skipjacks on Saturday from 1-5pm. All skipjack tours, rides and the race are free to any MD Seafood Festival attendee. The MD Seafood Festival offers visitors a vibrant waterfront with craft, artisan, recreational, and commercial vendors, 15 food vendors, and the Champions of the Chesapeake Interactive Education Village, where nonprofit organizations offer hands-on exhibits focusing on Bay history, ecology, and restoration.
The festival continues its mission to celebrate the living traditions of Chesapeake watermen while promoting education, conservation, and public access to this unique maritime heritage.
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Since 1959,
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Please join us for the Second Annual Skipjack Heritage Days at Sandy Point State Park on September 12-13, 2026
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The weekend will include maritime storytelling, live music, heritage presentations, a Sunday colorful parade of skipjacks, followed by a traditional skipjack race ant 12 noon organized with the Eastport Yacht Club.
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Contact- info@skipjack-nathan.org
See The "Last Skipjacks Project" website for further excellent information, pictures, etc.
Contact- skipjackupdates@gmail.com
