Skipjack Race

Celebrate Treasured Chesapeake Traditions

Skipjack Race

At the heart of Maryland, you’ll find the Chesapeake Bay. Celebrate this national treasure, its people and our traditions at these amazing events.

Watermen's Appreciation Day
Chesapeake Bay Maritime Museum, St. Michaels
Lighthouse and boats

Enjoy the beautiful St. Michaels waterfront for a spirited boat docking contest, steamed crabs and other delicious Eastern Shore favorites, plus live music, beer, boat rides, family activities and more.

Seafood Feast-I-Val
Steamed crabs

All-you-can-eat menu includes steamed crabs, crab soup, fried clams and more. Named a Top 100 event by the American Bus Association. Come out rain or shine to Sailwinds Park.

Pirates & Wenches Fantasy Weekend
Rock Hall
Pirates on boat

Town-wide theme party with fun for young and old. Live entertainment, grub and grog, merchants, artisans, decorated dinghy flotilla, beach party, buccaneer's ball, treasure hunt, costume contests and mayhem.

National Hard Crab Derby
Crab race

On Labor Day Weekend, beautiful Somers Cove Marina hosts this unique fair, with crab picking and eating contests, concerts, fireworks, a carnival and, of course, the National Hard Crab Derby where the fastest crustaceans on earth claw their way to the finish line.

Choptank Heritage Skipjack Race
Skipjack Race

This race provides an excellent opportunity to see most surviving traditional Skipjacks up close and under sail as they race on the Choptank River. The parade of Skipjacks and race start and finish are best viewed from Long Wharf Park while enjoying great local food and crafts.

Deal Island Skipjack Races and Island Fest
Deal Island
Skipjack Races

Spend your Labor Day Weekend on Deal Island and celebrate a Chesapeake tradition with three days of parades, a 5K, bike races, a fair, car show, local food and even the Miss Skipjack contest. Monday begins with the blessing of the boats then the Skipjack races begin. See boats and hard working crews battle to be the "fastest in the fleet."

Mid-Atlantic Small Craft Festival
St. Michaels

People have been building boats on the Chesapeake for thousands of years. This festival gathers hundreds of amateur and professional boat builders in an amazing flotilla of fun.

United States Powerboat Show

Miles of docks exhibit everything from luxurious motor and ocean-going yachts and “down east” trawlers to high-performance powerboats and offshore fishing machines. On display are boats of every style from 8’ to 80’ including express cruisers, inflatables, paddle boards, ski boats, trailerable powerboats, pontoons and an extensive collection of center console fishing boats.

United States Sailboat Show

Stroll the docks of Annapolis to scout out the latest collection of sailboats of all types and sizes from manufacturers around the world. Show tents line the shore where you can peruse nautical gear and accessories, equipment, sails and rigging. Find a sailing school, charter company, clubs and more to start your own adventure.

U.S. Oyster Festival
oyster shucking

Celebrate the opening of Maryland’s traditional oyster season at the U.S. Oyster Festival. Home of the National Oyster Shucking Championships and King Oyster. Find your favorite oyster recipe and see the oyster cook-off, with delectable horse d’oeuvres, soups and stews, and main dishes, then sample a wide variety of gourmet oysters in the oyster tasting tent, fresh from the Chesapeake Bay.

Blessing of the Fleet
Coltons Point
work boat

Blessing of the Fleet commemorates the founding of Maryland on St. Clement's Island and the time-honored tradition of blessing the Southern Maryland watermen's fleet of boats. This celebratory event includes tours of St. Clements Island, Blackistone Lighthouse & St. Clement's Island Museum, live entertainment, free boat excursions, Southern Maryland food, local wine tastings, arts and crafts vendors, children’s activities, fireworks and more.


TrawlerFest is a PassageMaker boat show, specifically designed for cruising-under-power enthusiasts. See the nation’s best in-water display of new and pre-owned cruising powerboats and enjoy first-class boating courses.