Deal Island Skipjack Races

Celebrate Treasured Chesapeake Traditions

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Deal Island Skipjack Races

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

1
National Hard Crab Derby - Crisfield
Crab race
Patty Hancock Photography

August 31-September 6, 2020

Through 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.

More info...

2
Choptank Heritage Skipjack Race - Cambridge
Skipjacks sailing during the Choptank Heritage Skipjack Race

September 26, 2020

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.

More information...

3
United States Powerboat Show - Annapolis
powerboat
United States Powerboat Show

October 1-4, 2020

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 water toys of all types, express cruisers, inflatables, paddle boards, ski boats, trailerable powerboats, pontoons, and an extensive collection of center console fishing boats.

4
Mid-Atlantic Small Craft Festival - St. Michaels
Couple sailing during the Mid-Atlantic Small Craft Festival
Chesapeake Bay Maritime Museum

October 2-3, 2020

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.

5
TrawlerFest - Baltimore
Power boat cruising the bay
TrawlerFest

October 6-10, 2020

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.

More information...

6
United States Sailboat Show - Annapolis
sailboat
United States Sailboat Show

October 8-12,2020

Bring the family to this world-famous sailboat show where you will find something for everyone; seminars, clothing & accessories, and boats of all sizes. Enjoy the many shops and restaurants in historic Annapolis.

7
U.S. Oyster Festival - Leonardtown
 National Oyster Shucking Championships
St Mary's County

U.S. Oyster Festival and National Oyster Shucking Championships.

October 17-18, 2020

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.

8
Watermen's Appreciation Day at the Chesapeake Bay Maritime Museum - St. Michaels
Watermen's Appreciation Festival
Chesapeake Bay Maritime Museum

The Talbot County Watermen's Association and the Chesapeake Bay Maritime Museum host the  Annual Watermen's Appreciation Day. 

Returning August 2021

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.

9
Seafood Feast-I-Val - Cambridge
Crabs in Crisfield
Somerset County Tourism

Returning August 14, 2021

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.

More info...

10
Pirates & Wenches Fantasy Weekend - Rock Hall
RockHallPirates.com

Returning August 2021

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.

More info...

11
Deal Island Skipjack Races and Island Fest - Deal Island
Deal Island Skipjack Race

Labor Day Weekend 2021

Concert on Saturday night. Sunday brings parades, dance, car show, music & local food. Monday begins with the blessing of the boats at 8am, Skipjack races start at 9:30. See boats & hard working crews battle to be the "fastest in the fleet."

More info...

12
Blessing of the Fleet - Coltons Point
work boat

Returning October 2-3, 2021

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, children’s activities, fireworks and more.