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, 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 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

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

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

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Anime Ocean City

Apr 27, 2024 - Apr 28, 2024

Anime lovers rejoice, Ocean City's newest annual event returns in April!

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May 4, 2024 - May 7, 2024

Celebrate Spring and the upcoming Summer season at Springfest's 33rd Anniversary!

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Jay Leno Live at the Performing Arts Center

May 16, 2024

Jay Leno performs live at the Ocean City Convention Center on May 16th, 2024!

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33rd Annual Cruisin’ Ocean City

May 16, 2024 - May 19, 2024

A 20+ 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.

PBR Bull Riding Ocean City

May 31, 2024 - Jun 2, 2024

Bull Riding returns to Ocean City, Maryland on May 31st!

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Ocean City Grand Prix 2024

Jun 7, 2024 - Jun 9, 2024

High speed boat racing along the Ocean City coast!

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Ocean City Jeep Week

Aug 22, 2024 - Aug 25, 2024

The biggest, most popular Jeep event in the mid-Atlantic returns to the Ocean City beaches on August 22nd!

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Ocean City Air Show 2024

Aug 24, 2024 - Aug 25, 2024

The Ocean City Air Show returns in August!

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Ocean’s Calling Music Festival

Sep 27, 2024 - Sep 29, 2024

A three day festival in partnership with musicians O.A.R. featuring over 30 performances on 3 stages, all on the classic Ocean City Boardwalk.

Country Calling Music Festival

Oct 4, 2024 - Oct 5, 2024

Country music takes over Ocean City, Maryland on October 4th and 5th, featuring over 25 artists and three different stages along the beach and boardwalk!

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Endless Summer Cruisin’

Oct 10, 2024 - Oct 13, 2024

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

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