The "City of Crisfield" races before the wind Labor Day 2005. Photo by Carolyn Kuchinski.

It was a beautiful Labor Day: fair wind and plenty of sun for the Skipjacks ready to sail in the 46th Oyster Fleet Race. The fleet was blessed at 8 a.m. and set out into Tangier Sound off Deal Island to prepare for the 9:30 start. As in all sail races, they tack and sail before the start line. Judging from the warning guns, they adjust in order to cross the start line just after the starting gun. They race a three-sided, 9-mile course, tacking their zigzag courses to Bell's Buoy, then down to the race buoy by Little Deal Island, and back up to the starting and finishing point.

It is a race run at three or four miles per hour in fair winds, longer if the winds die out, but the crews are trying every way they can to move the boat a little faster. They do this with 20 or so passengers riding on the deck enjoying the race until it ends at noon or before.

The competitors were familiar with the race and the course, since they have sailed this race many times over the years. The "Ida May" was captained by Captain Harold "Stoney" Whitelock of Chance. The "City of Crisfield" was sailed by Captain "Daddy" Art Daniels from Wenona. The "Fannie L. Daugherty" was captained by Captain Delmas Benton of Dames Quarter. Two relative youngsters filled out the rest of the field, the "Martha Lewis" with Captain Byshe Hicks from the Chesapeake Heritage Conservancy, and the "Nathan of Dorchester" owned by the Lundenberg School and sailed by Captain Frank Newton. While these last two are not now part of the oyster fleet, they race often and hard. They can win bragging rights, but not the prize money.

As Captain Delmas told me," It was a nice day…..and it would have been a better day if the 'Fannie L. Daugherty' had won." She was built in 1904 and captained by his father until 1989, when Captain Delmas bought her. He has raced her often since then, patching the sails and repairing her over the year for the next race.

At the start of the race, the "Fannie" and the "Martha Lewis" were almost neck and neck when the gun went off. The "Ida May" split off 10 feet of her boom, and Captain Stoney Whitelock and the crew jury-rigged her, finishing the race because that is what you do.

As they passed the first buoy and headed down to the race buoy by Little Deal Island, the "City of Crisfield," with Captain Art Daniels lagged behind, and the "Nathan of Dorchester" appeared a little sluggish to the other captains. All the boats were tacking and jockeying for position all the way down.

Rounding the race buoy down by Little Deal Island, the "Fannie" and "Martha" headed north on the last and longest leg of the race. Captain Art headed to the shallows with the "City of Crisfield." His boat drew the least water, and there was a fresh wind off the land. "Fannie" and "Martha" could not range as close to shore, but with almost a mile lead, they headed home as fast as they could.

While the "Ida May" struggled to finish the race behind the "Nathan of Dorchester," the "Martha Lewis" and the "Fannie L. Daugherty" fought to keep the lead from each other and "Daddy" Art with the "City of Crisfield."

It wasn't to be. Eighty-four-years-young Captain Art Daniels pulled the "City of Crisfield" into the lead and finished in first place. The "Martha Lewis" cut too far on her last tack and finished just before the "Fannie," with the "Nathan of Dorchester" next, and the "Ida May" finishing a tough race with her jury-rigged boom.

Captain Delmas and Captain Stoney gave all the credit to Captain Art with his 60 years of sailing skipjacks and his ability to head into the wind closer than his competitors. This is his fourth win in a row for the $1000 prize for first place. Second place wins $500, and any other working skipjack in the race gets the third place prize of $250.

Now we wait another year for another Labor Day to see these last representatives of a fleet that used to be a thousand boats strong race again for the bragging rights of the Eastern Shore of Maryland.

Bill Sailer is secretary of the Deal Island MD Lions Club.

© University of Maryland Eastern Shore, 2005. All rights reserved.