The 52nd Annual Skipjack Race and Festival
Deal Island Harbor
Route 363, Deal Island, Md.

Hours: Sept. 3 to 5
Price: $5 Admission (Monday only)
Additional information call Fred or Joanna Peak 410-784-2799

Between 1800 and 1900 the skipjack, a sail-powered workboat used primarily for oyster dredging, dominated the Chesapeake Bay waterways. In 1884 the Maryland oyster harvest reached its all-time peak at 15 million bushels. Today the harvest is less than 1 percent of the 1884 boom time. Estimates claim there are less than 20 working skipjacks left on the Bay. Those that remain are the oldest working fleet in America, and several individual skipjacks have been designated National Historic Landmarks.

Each year on Labor Day, some of the surviving Chesapeake Bay skipjacks sail to Deal Island Harbor in Somerset County to participate in the annual SkipJack Race now in its 52nd year. The fleet is blessed at 8:00 a.m. At 9:30 a.m., the boats leave the Deal Island Harbor and race a course marked out by buoys on the Tangier Sound. Spectators can watch from the sandy beach on the festival grounds or from kayaks, or boats. The first skipjack to complete the course is named the winner and any boat that hasn’t finished the race by noon, is assisted back to the harbor.

Rebecca Ruark

Photo Credit: Mindie Burgoyne

In 2010 11 skipjacks were entered to race in the 51st Annual Skipjack Race on Deal Island. The Rebecca T. Ruark, captained by Wade Murphy of Tilghman Island, won the race breaking the record for the winningest skipjack to compete in these annual races. The Rebecca T. Ruark won her first race in 1988 and began a seven-year winning streak taking first place through 1994. She won again in 1996 and 1997. The 2010 race was her eleventh win beating the 10-win record of the legendary F C Lewis, captained by Stanford White Jr. (now deceased). Hot on the winning trail of the Rebecca T. Ruark is the City of Crisfield, captained by Art “Daddy Art” Daniels of Wenona. The City of Crisfield had her first win in 1965 and eight subsequent wins placing her second for most number of wins for the Annual Skipjack Races. The Rebecca T. Ruark and the City of Crisfield are two of the expected 13 skipjacks to race this Labor Day.

Captain Wade Murphy being interviewed by reported Ko Im

Photo Credit: Mindie Burgoyne

The Kathryn, once famous for her first skipjack race in 1975 with captain John Parkinson, fell into disrepair and wasn’t seen for years. Harold “Stoney” Whitlock, from a family with three generations of skipjack captains, resurrected the Kathryn, and will be racing her in this year’s race.

The Skipjack Race and Festival is held on the festival grounds at the Deal Island Harbor, which is just over the bridge connecting the island to the mainland. The weekend festival includes games, amusements, art and craft vendors, food, raffles, live entertainment, a parade, swimming contest, boat docking contest and live entertainment that includes four music acts.

While the race is the main event, the boat-docking contest comes in a strong runner-up. There are three competitions – large boats, small boats, and team boats. The largest purse ($1,000) goes to the winner of the team boat competition where at least two people have to work together while the boat is moving. Spectators hold their breath anticipating a “man overboard” call during this tenuous process.

This event is a wonderful family experience, packed with culture, scenic landscapes, local food, art and entertainment for all ages. Visitors can swim and launch kayaks from the beach. Even the family dog is welcome to attend (and swim). Bring a folding chair, a blanket, camera and some binoculars, and prepare to have a memorable, culturally authentic outdoor experience. The proceeds from the Annual Skipjack Race and Festival go to the main sponsor, the Deal Island Lions Club, well known for helping local families in need. Most of the Lions’ annual budget comes from this single event.

Mindie Burgoyne is an author, travel writer and tour guide living on the Eastern Shore of Maryland. Her blog The Travel Hag shares information on outdoor travel for women. She is the author of Haunted Eastern Shore; Ghostly Tales from East of the Chesapeake.

Comments (5)
  1. Chesapeake Bay Maritime Museum says:

    Great story! And the Chesapeake Bay Maritime Museum in St. Michaels, MD can’t wait til our skipjack Rosie Parks, once a winner in this longstanding race, has her restoration complete, her sails up, and can participate in this longstanding tradition. They are all so beautiful, and their captains and crews the fabric of Chesapeake life.

  2. Karts Huseonica says:

    We’re looking forward to the races on Monday, and seeing modern country singer Ashley Forrest perform. Thanks to Fred, Joanna, and all the other volunteers who make this festival a great family tradition. Be safe. Karen & Art Huseonica

  3. Mindie Burgoyne says:

    Can’t wait to see Rosie Parks! The Chesapeake Bay Maritime Museum plays a key role in the Maryland skipjack fleet. And it’s true. The folks in Chance and Deal Island – specifically the Lions Club do a great job with this festival. Stop by and see me at the races. I’ll with the family lined up in chairs across the beach.

  4. Wendy says:

    Great story Mindie, but I have a slight correction: There is no charge for admission on Saturday or Sunday during the day. There is a $5 charge/person for the dance Sunday night. Monday is the only day they charge admission to the fairgrounds and you can purchase an all day wristband for $5. For the Gospel Concert Saturday night, offerings are accepted. Thanks!

  5. Mindie Burgoyne says:

    Thanks, Wendy. My mistake. Checked back in my notes and see that I typed the date incorrectly. Glad you checked. I’ll see if I can get the editor to make the correction.

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