Have you made plans yet to visit Somerset County, MD this Labor Day weekend? Round out your visit to Great Hope Golf Course with enticing annual events happening in Crisfield and Deal Island, MD. 

After you golf a quick 6 and have a meal at the Caddy Shack, head to the National Hard Crab Derby or the Skipjack Race and Festival for live music, vendors of all sorts, and an array of contests that will keep your foursome entertained all weekend long! 

Pair a Golf Weekend with Labor Day Festivals in Somerset County, MD 

Labor Day weekend is the perfect time to spend a few days enjoying the local scene in Crisfield and Deal Island, MD. You’ll get to enjoy local crab feasts and watch contests you’ll only find on the Eastern Shore! From boat docking to crab racing, it’s sure to be a weekend to tell your golf buddies about for next year! 

79th Annual National Hard Crab Derby 

September 4-6, 2026 in Crisfield, MD

Featuring: 

• Main Street Parade
• Mike Sterling 10K
• Crab Races
• Crab Picking Contest
• Boat Docking Contest
• Carnival with Food and Craft vendors 
• Live Entertainment

Get all the event details at Visit Somerset. 

Deal Island-Chance Lions Club 67th Annual Skipjack Race and Festival 

September 6 and 7, 2026 in Deal Island, MD 

Sunday, September 6, 2026

Admission free until 4 p.m. After 4 p.m., admission is $10, and kids under 12 are free. 

• Church Services, Car Show 
• Parade at 1 p.m.
• DJ Carpe Diem from 2 – 5 p.m. 
• Elvis Tribute Artist, David King & The Spin Outs at 5 p.m.
• Bare Bones Time Machine at 7 p.m.

Monday, September 7, 2026

Admission is $10, and kids under 12 are free.

• 67th Annual Skipjack Race, Sponsored by Skipjack Heritage at 9:30 a.m. 
• Working Waterman’s Team Boat Docking at 2 p.m.
• Silent Auction, Raffle, Food Vendors, Fishing Tournament, and more. 

Peruse Great Hope Golf Course through our virtual course tour. Find a full event schedule, lodging information, and dining recommendations from Visit Somerset.