Mark Your Calendars: September Events You Don’t Want to Miss

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With only a few days until September, we are looking forward to what the fall months are going to bring – and one of those things is some of the best events of the year!

Wine on the Beach (9/8-9)
Whether you’re a wine connoisseur or just want to do some taste testing, the Wine on the Beach Festival is a great place to try the best wines, beers, and food Maryland has to offer. Also, while you’re there, browse vendor tents selling gorgeous art and handmade products and jam to live music from local artists like Larry Lay, Bird Dog & the Road Kings, Misspent Youth, and Tranzfusion.

Tickets are $35 and include a wine glass and samples, and can be purchased in advance on their website, winefest.com. You can even bring your family if you want to. Tickets for children 13-20 are $15, and children under 12 are free!

Bikefest (9/13-17)
The largest motorcycle rally on the East Coast is back for another year! From a boardwalk parade to shopping, concerts and more, BikeFest is one of the most exciting weeks of the year. With big names like Joan Jett, Billy Idol, Lynyrd Skynyrd, and more are set to perform, it’s sure to be a week to remember!

Check out ocbikefest.com for more information about the rally!

AdventureFest (9/22-24)
Back for their second year, AdventureFest is a hunting, fishing, and gun show, featuring activities like K9 training, C.O.P.S. support meetings, hunting and fishing expos, a H&H memorial walk, and even a motorcycle rodeo. The event also includes live music performances by artists such as Don McLean of “American Pie” fame and David Bray, as well as auctions for custom items like a gun, surfboard, and autographed guitars. Proceeds will benefit various non-profits supporting law enforcement, military personnel, and veterans. The festival runs from September 22nd to 24th at the Roland E. Powell Convention Center.

You can purchase concert tickets at ocadventurefest.com.

Ocean’s Calling (9/29-10/1)
After being canceled last year due to severe weather, Ocean’s Calling is back and better than ever! This live music and food festival is unprecedented for the town bringing world-renown names like John Mayer, Alanis Morissette, Jack Johnson and The Lumineers – just to name a few.

But the exceptional music line-up isn’t the only exciting thing happening. Celebrity chefs, Robert Irvine, famous for his Food Network programs, Dining: Impossible and Restaurant: Impossible, and Amanda Freitag, best known for her appearances on Chopped, will be doing cooking demos, and revealing “tricks of the trade” for festival goers.

Tickets are limited, but still available at oceancscallingfestival.com

With something happening every weekend, it’s sure to be an exciting September! We hope to see you, and as always, check out our hotels for the best oceanfront accommodations!

Upcoming Events

Ocean City Running Festival

Nov 14, 2026

Join the Ocean City Running Festival on November 14th, 2026!

2026 Winterfest of Lights

Nov 19, 2026 - Dec 31, 2026

Experience the magic of the holidays at Winterfest of Lights in Ocean City, MD. Enjoy over a million twinkling lights, festive train rides, and seasonal fun for all ages!

Ocean City Christmas Parade

Dec 5, 2026

Celebrate the holiday season at the Ocean City Christmas Parade! Enjoy festive floats, marching bands, and a special appearance by Santa Claus along Coastal Highway.

Ocean City Comic Con 2026

Dec 12, 2026 - Dec 13, 2026

Join us for a weekend full of comics, guests, panels, screenings, cosplay, video game tournaments, and so much more right here on the shore!

Terry Fator’s A Very Terry Christmas

Dec 19, 2026

Terry Fator will be performing at the Ocean City Performing Arts Center on December 19th!

Dreamfest Events 2026

Jan 15, 2027 - Jan 17, 2027

Join us for three unforgettable days filled with a vibrant fusion of music and fun!

34th Annual Cruisin’ Ocean City

Apr 29, 2027 - May 2, 2027

A 30+ year car show that will feature over 3,000 Hot Rods, Customs, Classics, and Trucks participating in events at the OC Convention Center, Inlet Parking Lot, and various car shows throughout town.

Boardwalk Rock Festival

May 14, 2027 - May 16, 2027

Ocean City's Newest and Biggest Music Festival!

Ocean City Air Show 2027

Jun 19, 2027 - Jun 20, 2027

The Ocean City Air Show returns in June!

Endless Summer Cruisin’

Oct 7, 2027 - Oct 10, 2027

If you miss Cruisin' OC in May, you get another chance to see more hot rod action in October!

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