Events on Maryland’s Eastern Shore

Find upcoming events on Maryland’s Eastern Shore, including festivals, live music, arts and culture, food and drink events, and seasonal celebrations. This local events calendar highlights what’s happening in Easton, St. Michaels, Oxford, Chestertown, and nearby Eastern Shore towns, making it easy for visitors and residents to plan their time in the area.

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Skipjack Race & Festival

September 1, 2024 @ 9:30 am - September 2, 2024 @ 5:00 pm

Festival Grounds includes Food Vendors, Arts & Crafts Vendors, Heritage & Education Exhibits and free Children’s Activities, both Sunday and Monday

The Deal Island (Md.) Skipjack Races happen on Labor Day Monday, Sept. 2. As always, the Island Fest on both Sunday and Monday offers a variety of events—parade, live music, car show, blessing of the fleet, boat-docking contest, more. Details.

Event Schedule

Sunday

 FREE ADMISSION 

9:30 am – Church By The Bay Service

10:00 am – Car Show Registration

10:00 am – Ticket Raffle Sales Begin (1 day only) – ends 4:00 pm

1:00 pm – Parade (line-up 12:15 pm at the school)

2:00 pm – Rock Creek Band

7:00 pm – AJ the DJ – $5.00 admission

Monday

$10 Admission – Ages 13+

Kids 12 and under free

Sunrise to 2:00 pm – Stan Yastrzemsky Memorial Fishing Tournament

7:00 am – Fire Dept. Auxiliary Breakfast Sandwiches

8:00 am – Blessing of the Fleet

9:00 am – Heritage & Education Exhibits

9:00 am – Preferred Handicap Factor

9:30 am – 65th Annual Skipjack Race

10:00 am – Silent Auction (1 day only) – ends 4:00 pm

10:00 am – Fire Dept. Auxiliary Bake Sale (ends at 2 pm)

1:00 pm – Working Waterman’s Team Boat Docking Practice Round

2:00 pm – Working Waterman’s Team Boat Docking Qualifying and Contest

5:00 pm – Cash Raffle Drawings (Miss Skipjack)

5:00 pm – Award Ceremony

Organizer: Secrets of the Eastern Shore

Venue: The Deal Island (Md.)

 

Details

Details