Summer is when the Eastern Shore shines the brightest! July and August are some of the best times to explore our coastal towns, waterfront views, and enticing events that give you a real sense of our community. From Crisfield to Princess Anne, MD, it’s time to visit Somerset County, MD for the Somerset County Fair, the Wheels on the Waterfront Cruise In, and Labor Day weekend events—you won’t regret it!
July Events Near Crisfield, MD: Somerset County Fair, and WOW Cruise
Plan your stay in Somerset County, MD for a summer full of fun! For information on lodging, restaurants and eateries, shopping, and sightseeing, let Visit Somerset be your guide.
Somerset County Fair
July 24-26, 2026
8 a.m. to 8 p.m.
Somerset County Civic Center, Princess Anne, MD
Join us for an old-fashioned county fair with a patriotic twist as we celebrate America’s 250th Anniversary. The Somerset County Fair will feature an extensive vendor mall, livestock exhibits, a kids watermelon eating contest, a greased pig contest, a cake auction and so much more. View the full Fair Book and schedule.
19th Annual WOW Cruise-In
July 25, 2026
3 - 7 p.m.
1200-1300 West Main Street, Crisfield
The Wheels That Heal Car Club is hosting their 19th Annual Wheels on the Waterfront Cruise-In, inviting classic cars and trucks, street rods, and custom motorcycles for the area’s best charitable car cruise. With exhibitor door prizes, 50/50 charity raffle, and dash plaques for the first 150 entrants, the annual event benefits the Crisfield Lions Club and the Crisfield Lioness Club.
Save the Date for Labor Day Weekend Events in Somerset County
79th National Hard Crab Derby
Sep 4, 2026
All Day Event
Somers Cove Marina, 715 Broadway, Crisfield, MD 21817
Celebrate the heritage and traditions of the “Crab Capital of the World” during the 79th Annual Hard Crab Derby. The event features crab races, boat docking, crab cooking and picking contests, artisans, live musical entertainment, beauty pageants, parade, fireworks and more.
Deal Island Skipjack Races and Land Festival
Sep 5, 2026
6 a.m. - 10 p.m.
Deal Island Harbor Beach
Watch stately single-masted oyster boats race across the water, vying to earn both a prize and to claim victory for the next year! In addition to the races, the event includes a parade, concerts, working waterman's boat docking competition, and more, hosted by the Deal Island Lions Club and Skipjack Heritage, Inc.
Can’t make these events? Find more great opportunities to visit Crisfield, Princess Anne, and Smith Island, MD!
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