CAMBRIDGE – Sail-powered workboats (skipjacks, bugeyes, log canoes) started racing 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 were out on the water together, rivalries were formed, and side bets were made.

Informal races occurred up and down the bay from Havre de Grace to Solomons Island and were popular at Crisfield, Rock Hall, Claiborne, Annapolis, Oxford, Cambridge, and Deal Island.

One hundred years ago, skipjacks competed in races across the Chesapeake Bay. Today only two skipjack races remain. The Labor Day race and carnival at Deal Island is now in its 62^nd year. The Deal Island race is held in Tangier Sound and is best seen by boat.

The 27^th Choptank Heritage Skipjack Race will be held Sept. 23 in Cambridge. The race is sponsored by the Dorchester Skipjack Committee, with the host Skipjack being Nathan of Dorchester.

This year the Nathan of Dorchester will have an all-female crew. This has only been done once before, on the Helen Virginia, with Captain Katarina Ennerfelt in 2014.

The Nathan of Dorchester will be commanded by Capt. Michele Drostin. This is a first for the Nathan of Dorchester. Though about half of the Nathan crew are women, there are heavy tasks so the crew is usually a mix of men and women working together.

This race crew is excited to show that they can manage the “heavy lifting” as a team. They have been sailing as a group since July learning how to race this beautiful authentic Chesapeake Bay skipjack.

The women have a wide range of sailing experiences. Captain Drostin has been sailing and teaching sailing for 30 years on all sizes of boats. She has been a captain on the Nathan for three years.

Her tactician, Cathy Schmidt, has raced on the Bay since she was a young girl growing up in Oxford. Other crew members like Mary Handley have a passion for the Nathan and have been sailing her for almost 10 years.

Kim Stevenson is another seasoned sailor, who has sailed all over the world on larger boats.  Jean Knauer grew up sailing on the Choptank. Maureen Smith, Julie Schoch and Julia Strong have learned to sail as crew on the Nathan. The newest member of the crew, Renee North, joined this year.

Sailing as a group has been an incredible experience. They are practicing and learning to work smarter, improve her maneuvers and get across the start and finish line efficiently.

The race starts and finishes by the Choptank River Lighthouse. The Nathan of Dorchester will lead the boat parade out of Cambridge Creek at 9 a.m. Racing begins at 10 a.m.

The Lighthouse deck and adjacent floating dock offers spectators an excellent view of the race at Long Wharf Park, at the foot of High and Water Streets in Cambridge. 

The race helps preserve the remaining skipjacks. Each participating skipjack receives approximately $700 in show-up money, for boat maintenance and preservation. Over the past 20-plus years, the Dorchester Skipjack Committee has raised and donated over $100,000 to help preserve the skipjack fleet. The Dorchester Skipjack Committee is a 501(c)3 organization.