Nathan of Dorchester and Skipjack Races

The skipjack Nathan of Dorchester will be busy in September participating in two away skipjack races and hosting the Choptank heritage skipjack race September 27th in Cambridge.

On Labor Day, Nathan will join many surviving skipjacks to race and celebrate the maritime heritage of local watermen at the 67th annual Deal Island race. This race is held in Tangier sound and is best seen by boat. On September 14th, after a 20-year lapse, Nathan will join other skipjacks to race again at Sandy Point State Park. This Sunday race is part of the 2025 Maryland Seafood Festival. Unfortunately, the best views of this race will be from westbound traffic stalled on the Bay bridge.

For stress free close-up views of skipjacks under sail, join us at the 29th Choptank Heritage Skipjack Race in Cambridge on  September 27th. This race is sponsored by the Dorchester Skipjack Committee and the host Skipjack Nathan of Dorchester. The race starts and finishes in Cambridge harbor by the lighthouse and offers spectators an excellent close up view of the boats under full sail. A parade of boats will head out of Cambridge Creek at 9 a.m. with the race starting at 10 a.m. The best view is from the floating dock at Long Wharf Park, at the foot of High and Water Streets in Cambridge, MD. The race is a free event but there will be an opportunity to help keep our skipjacks afloat. Contributions can be placed in our race day “Donation Dingy” or by credit card or PayPal through the web site www.skipjack-nathan.org. 

Skipjack races started as informal sail powered workboats raced back in 1872 when local watermen took their boats and crews out on shakedown sails before the start of the oyster season. Whenever two or more boats are out on the water together, rivalries were formed, and side bets were made. Every waterfront town had workboat races. During the roaring 1920’s, 99 sail powered workboats raced at Deal Island. Today perhaps as many as 10 surviving skipjacks will compete. 

With sponsorship from the Baltimore Sun newspapers and political support from the governors of Maryland and Virginia, Chesapeake Bay Championship Workboat Races became popular events in the 1920’s. 

So many boats competed in the statewide Championship Workboat Races that 30 closed deck (larger) skipjacks raced in one category, and a separate category was established for now forgotten open deck (smaller) skipjacks. Two classes of bugeyes raced. Only the bugeye Edna Lockwood survives and sails today. Working and racing log canoes held their own races. Only a small number of racing canoes survive and sail today. With most types of sail powered workboats fading memories, today’s races pit skipjacks against other skipjacks with the bugeye Edna Lockwood occasionally sailing with spectators.

In the 1920’s, Choptank River bugeyes and skipjacks dominated statewide races. The Baltimore Sun reported that “Cambridge boats showed boats up and down the Bay that they were clear winners.” First prize in each race category was $100, a new set of sails, and a trophy. In 1925, the Cambridge skipjack Agnes placed first; Oxford skipjack Elmer E placed second with Rebecca T Ruark coming in third. The Rebecca T Ruark still sails today, repaired after being seriously damaged three years ago when a pickup truck accidentally parked on her deck.

Today’s Skipjack races are less about fierce competition and more about preserving the remaining skipjacks and telling stories about our maritime heritage. Each skipjack participating in the races receives show-up money for boat maintenance and preservation. In support of the Choptank Heritage Skipjack Races, the Dorchester Skipjack committee has raised and donated well over $150,000 to participating boats to help preserve the skipjack fleet.

The Dorchester Skipjack Committee, Inc., is a 501(c)3 nonprofit organization. Your donations are tax-deductible to the extent allowed by law.
Donations also may also be made payable and mailed to:
The Dorchester Skipjack Committee, Inc.
P.O. Box 1224
Cambridge, MD 21613