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ISLE OF WIGHT & ASSAWOMAN BAY

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Isle of Wight & Assawoman Bay Maryland Events, Concerts, Festivals and More!

  1. « Eastern Shore Rentals

ISLE OF WIGHT & ASSAWOMAN BAY

Looking for things to do on your trip? Our local events guide for Isle of Wight & Assawoman Bay Maryland highlights festivals, concerts, and seasonal celebrations happening year-round. From family-friendly activities to live entertainment and cultural experiences, there’s something for everyone.

📆 May

Event Travel
May • Ocean City Maryland

Springfest Ocean City Maryland

4 day Music and Art festival located on the iconic Ocean City Maryland boardwalk.

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Event Travel
May • Ocean City Maryland

Cruisin Ocean City Maryland Car Show

Ocean City Maryland citywide car show featuring the boardwalk display. Thousands of cars, trucks, parades, live music, entertainment and more.

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📆 September

Event Travel
September • Ocean City Maryland

Oc Bikefest

OC BikeFest will bring national entertainment and bands, stunt shows, bike builders, vendors, food and beverage to the Boardwalk, Convention…

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📆 October

Event Travel
October • Ocean City Maryland

Annual Cruisin' Ocean City Maryland

This popular car show features over 3,400 hot rods, customs, classics, street machines, muscle cars and more. Live entertainment, celebrity…

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📆 November

Event Travel
November • Ocean City Maryland

Winterfest Of Lights Ocean City

Board the Winterfest Express and prepare to be whisked into a magical land of spectacular lights. Displays include the Twelve Days of Christmas,…

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