Here are our top events happening in Ocean City during May.
By Chris Murphy
The month of May is full of fun and exciting events in Ocean City. Whether you’re searching for family-friendly events, food and drink events, live music or free festivals, you’ll have plenty of options to choose from. Be sure to pick up an Ocean City Visitors Guide to find even more events happening throughout the year.
Ongoing-May 3: Cruisin’ Ocean City
The 36th Annual Cruisin’ Ocean City returns April 30 – May 3, 2026. As one of the East Coast’s premier automotive events, it will host over 3,000 customs, hot rods, and classic cars. While the beachside Inlet Parking Lot serves as the epicenter, car shows and activities will span throughout the town.
Special Guests: Emily and Aaron Reeves from Flying Sparks Garage will showcase their custom 1984 Peterbilt, “Optimus Grime,” from April 30 to May 2.
Live Music: On Thursday, April 30, the acclaimed Beatles tribute band, The Fab Four, performs their Help! show at the Ocean City Performing Arts Center. Expect an authentic 1960s experience featuring iconic hits and costumes.
Don’t miss this four-day celebration of automotive culture and timeless music. Tickets for the stage show are available now.
Ongoing-May 11: Ocean City Restaurant Week
Participating Restaurant Week establishments are given the freedom to offer whatever best fits for their restaurant at this time. Several will offer Restaurant Week fixed price menu options others may offer great deals – all will offer you a variety of dining options. RW offers a chance to try new food, a new place, or a chance to dine at your favorite place – make plans to dine out and support local restaurants!
If possible, we highly recommend making reservations in advance. Don’t miss out on Ocean City Restaurant Week!
May 8-10: ESA’s 2026 Northeast Regional Surfing Championship
The ESA’s 2025 Northeast Regional Surfing Championship will bring the best amateur surfers from Maryland through Maine, including the Great Lakes, to compete for a chance to qualify for the ESA’s 2025 Easterns Surfing Championship. Over 200 competitors of all ages and surfing abilities will be putting on a show in Ocean City’s waves. This is a free, family-friendly event that will be held in midtown Ocean City over three days. Come out and watch in person, or tune in to watch on the livestream that will be up during all hours that event is running.
Want more Events?
CALENDAR: Check out our Ocean City calendar of events to help plan your activities!
NEWSLETTER: Or sign up for our Ocean City Destination Newsletter to receive exclusive content for planning your vacation getaway to Ocean City!
