Ocean City, Maryland, is buzzing with excitement this fall! From beachfront music festivals to classic car shows and beloved seasonal traditions, there’s no shortage of ways to celebrate the season. Here’s your ultimate guide to the biggest events happening from September through November 2025.
Music Festivals on the Beach
Oceans Calling Festival (Sept. 26–28, 2025)
One of Ocean City’s largest music events returns to the Inlet with headliners like Green Day, Noah Kahan, and Fall Out Boy performing across multiple beachfront stages. Expect incredible live music, local food vendors, and plenty of energy.
Country Calling Festival (Oct. 3–5, 2025)
Just a week later, the stage transforms for country’s biggest names, including Luke Combs and Carrie Underwood. This festival brings Nashville vibes to the shore with three days of unforgettable performances.
Car Shows & Classic Favorites
Endless Summer Cruisin’ (Oct. 9–12, 2025)
A tradition for car enthusiasts, this show will feature more than 3,000 classic cars, hot rods, and trucks throughout the Convention Center and Boardwalk. Perfect for anyone who loves chrome, horsepower, and nostalgia.
Sunfest (Oct. 23–26, 2025)
The season’s signature arts and crafts festival takes over the Inlet lot with handmade goods, live music, and delicious Eastern Shore eats. Sunfest is the perfect mix of shopping, food, and entertainment.
Other Fall Highlights
Wine on the Beach (Sept. 5–6, 2025)
Kick off the season by sampling regional wines, browsing artisan vendors, and enjoying live music in a relaxed bayside setting.
OC Rock and Ride (Sept. 10–14, 2025)
Motorcycle enthusiasts won’t want to miss Bike Week, featuring demo rides, live concerts, and vendor showcases across Ocean City.
Sunfest Kite Festival (Sept. 18–21, 2025)
Look up! Giant colorful kites will fill the sky during this family-friendly event hosted by The Kite Loft on the beach.
Holiday Kickoff Events
Winterfest of Lights (Nov. 20–Dec. 31, 2025)
As fall winds down, Northside Park transforms into a dazzling holiday wonderland with twinkling light displays, themed exhibits, and plenty of family fun.
Rising Tides Festival (Nov. 22, 2025)
A brand-new addition to Ocean City’s fall calendar, this unique festival highlights coastal culture and community with live entertainment, vendors, and seasonal activities.
Whether you’re here for the music, the classic cars, or the festive atmosphere, Ocean City’s fall lineup has something for everyone. Mark your calendars now and don’t miss a season packed with unforgettable events!