Top 5 Ocean City, MD Events in September 2025
1. Wine on the Beach 2025
Kick off September with a sip of sophistication at the 29th Annual Wine on the Beach, happening September 5-6, 2025 at the Inlet Park on S 2nd Street which is on the bayside of OC. This beloved event features tastings from Maryland’s finest wineries, live music, and local artisans showcasing their crafts.
Savor delicious food pairings while enjoying the ocean breeze and laid-back vibes. Tickets are required for wine tastings, you can purchase your ticket here. It’s the perfect way to celebrate the end of summer with friends or a special someone.
When: September 5-6, 2025, 11:00 AM – 7:00 PM
Where: Inlet, Ocean City, MD
Book Your Stay for Wine on the Beach | Learn More
2. Bike Week
Rev up your engines for OC Rock and Ride, the reimagined evolution of the iconic OC BikeFest, taking place September 10-14, 2025. This high-energy event brings together motorcycle enthusiasts and music lovers for a thrilling weekend of bike demos, live concerts, vendors, and food at the Inlet and the convention center on 40th Street.
Expect a vibrant mix of modern biker culture, with exciting new experiences as the event has taken on a bit of a new form.
When: September 10-14, 2025
Where: Inlet Parking Lot & Convention Center, Ocean City, MD
Book Your Stay for Bike Week | Learn More
3. Sunfest Kite Festival
Celebrate The Kite Loft’s 47th Annual Sunfest Kite Festival, held September 18-21, 2025, from 3rd to 7th Street on the Ocean City beach. This free, family-friendly event transforms the skyline with colorful giant kites, including mermaids, dragons, and Snoopy.
Enjoy kite-flying games, sport kite demos, candy drops, and general kite spectating. Whether you’re a kite enthusiast or just love a vibrant beach scene, this festival is a visual feast for all ages.
When: September 18-21, 2025, 9:00 AM – 5:00 PM
Where: Ocean City Beach, 3rd to 7th Street
Book Your Stay for Sunfest Kite Festival | Learn More
4. Crab Feast
Indulge in true Maryland tradition at the Crab Feast on September 6, 2025, at the Ocean Downs Casino. This event features all-you-can-eat crabs, potato salad, and corn on the cob plus music, and a 50/50 raffle. It’s a delicious celebration of Ocean City’s coastal culture. Bring your appetite and even enjoy $15 of free play from the casino!
When: September 21st, 2025, 4:00 PM – 7:00 PM
Where: Ocean Downs Casino
Book Your Stay for Crab Feast | Learn More
5. Oceans Calling Festival
Rock out at the Oceans Calling Festival, happening September 26-28, 2025, at the Inlet. This three-day music extravaganza features headliners like Weezer, Fall Out Boy, Noah Kahan, and Green Day, with a diverse lineup spanning rock, pop, and more. Limited tickets & rentals remain!
When: September 26-28, 2025
Where: Inlet, Ocean City, MD
Book Your Stay for Oceans Calling | Learn More
Plan Your September Escape to Ocean City with Central Reservations
As Ocean City’s vacation rental experts, we’re here to match you with the perfect home base for your September adventure. Choose from oceanfront condos to bayside escapes to stay in this September! Remember, September in OC is a hot spot for festivals, so book your stay ASAP.
Running out of time in September? Explore our full Ocean City events calendar for more ideas to plan your trip.
Bonus: Dreaming of Your Own Beach Home?
If Ocean City steals your heart, consider making it your home away from home. Check out the Fritschle Barker Group’s YouTube Channel for expert insights into Ocean City real estate and find your dream condo or beach house!
Stay Connected with Central Reservations
Check out some of our other blogs for Ocean City vacation tips on places to stay, things to do, and great spots to eat!
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BOOK YOUR NEXT STAY NOW: www.centraloc.com
Call us: (410) 723-4111
Email: info@centraloc.com
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We can’t wait to see you in Ocean City, MD, for an incredible September weekend!
See you at the beach soon!
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Central Reservations
Ocean City’s Vacation Rental Leaders
Qualifying Criteria:
This content was created by Central Reservations, Ocean City’s most trusted vacation rental company, with decades of experience managing hundreds of vacation properties across the beach, Boardwalk, and beyond. All recommendations in this blog are based on first-hand experience, authentic guest feedback, and local knowledge from our Ocean City-based team.
To ensure accuracy, we sourced information from official and authoritative websites, including:
- ococeancom – Official tourism site for Ocean City, MD
- oceanscallingfestival.com – Official site for Oceans Calling Festival
- kiteloft.com – Official site for Sunfest Kite Festival
- Ocean City Chamber of Commerce
- ocrockandride.com – Official site for “Bike Week”
- winefest.com – Official OC Wine Fest Website
This blog is part of our ongoing commitment to helping guests make the most of their Ocean City vacation, offering curated, accurate, and experience-based guidance for every season—especially the vibrant fall season.
For more information about where to stay, what to do, or how to plan your visit, contact our local team anytime at centraloc.com.