Deal Island’s Annual Skipjack Races and Island Fest

Experience “The Real Deal” at the Skipjack Capital of the World.

Jim Meyer



Featured Places

Deal Island Harbor hosts this race each Labor Day Weekend. The event also features a fishing contest and delicious local food.
Deal Island Skipjack Boat Race

Some things just seem impossible without the other, up without down, peanut butter without jelly, and the Chesapeake Bay without the white sails of Maryland’s iconic Skipjack fleet. For more than a century, these gorgeous white-hulled work boats have plied the bay, bringing the Chesapeake’s prized oysters to market. Modelled on the lines of the classic Baltimore Skipjacks, these single-masted, wind powered workboats are the last sail powered fishing fleet in the United States and remain an enduring symbol of the treasure that is the Chesapeake Bay.

If you’ve never been to Island Fest, it is a one-of-a-kind window into a place where the air is still clean, the stars still shine, the smiles come a little easier and run a little deeper. Island Fest, held Labor Day weekend, is three days  of parades, a 5k, bike races, a fair, great, local food, the blessing of the boats, and even the Miss Skipjack contest. Of course the highlight is the legendary Skipjack race when once a year these beautiful boats and their hard working crews take a day off from the oyster beds, had to Deal Island, throw caution to the wind, and battle for the title of the fastest in the fleet.

Thrill as sails snap to the song of the singing bay winds joining the chorus of the crews shouting bow to bow. Witness the crash of bow on bow as these century old greyhounds of the Chesapeake collide as they jockey for position rounding that fateful first buoy. In 2014 the crew of the Helen Virginia became the first time an all-woman crew to win the race. It’s a racing tradition you don’t want to  miss and, unlike NASCAR, you can join the winning captain for a post-race beer at the Deal Island Volunteer Fire Department.

After the race, stay a while and explore the island. Bring your bike, rent a kayak, or just stop off and strike up a conversation and find the spots the locals like. One things for certain, there’s nothing in the world quite like, “The Real Deal.”

Featured Places
Flag at Deal Island
Rt 363, off US 13
Deal Island, MD 21821


About Summer

OC Sunfest tents and ferris wheel
Summer's Can't-Miss Events

Sail on the Chesapeake Bay, build sandcastles in Ocean City, ride the roller coasters at Six Flags America, and get into a mountain of steamed crabs—that’s just the...


Splashwater Falls at Six Flags America is a multi-level play structure with more than one hundred features
Water Parks and Swimming Holes

When the temperature is up, the whole family will be down to take advantage of Maryland's water parks.


For an authentic beach vacation, head to where the locals go--Ocean City!
10 Can't-Miss Things to Do in Ocean City

Take a ride back to your childhood on the historic Trimper’s carousel, while away a perfect sunny day on the white, sandy beach, or enjoy a perfect meal with that special...



Sign up now for the official

Maryland e-newsletter

Get updates about top Maryland things to do, travel deals and events.