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

White Marlin Open

Aug 4, 2025 - Aug 8, 2025

Join the excitement of the White Marlin Open in Ocean City, MD, the world's largest billfishing tournament with thrilling weigh-ins and big prize money!

Oceans Calling

Sep 26, 2025 - Sep 28, 2025

Experience the Oceans Calling Festival in Ocean City, MD – a multi-day celebration of live music, local food, and coastal vibes on the iconic boardwalk!

Country Calling

Oct 3, 2025 - Oct 5, 2025

Sing along to top country artists at the Country Calling Festival in Ocean City, MD. Enjoy live music, local food, and a scenic beachside atmosphere!

Endless Summer Cruisin’

Oct 9, 2025 - Oct 12, 2025

Rev up your engines at Endless Summer Cruisin' in Ocean City, MD! Enjoy classic cars, hot rods, motorcycle shows, cruises, and more in a scenic beachside setting!

Sunfest

Oct 23, 2025 - Oct 26, 2025

Experience Sunfest in Ocean City, MD – a vibrant festival featuring live music, local arts, delicious food, and family-friendly fun along the beautiful waterfront!

Ocean City Running Festival

Oct 31, 2025 - Nov 1, 2025

Join the Ocean City Running Festival for a scenic race along the iconic boardwalk and beautiful coastal views. Choose from a marathon, half marathon, 5K, and more!

2025 Winterfest of Lights

Nov 20, 2025 - Dec 31, 2025

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!

Rising Tides Festival

Nov 22, 2025

Ocean City Christmas Parade

Dec 6, 2025

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.

New Year’s Eve Fireworks

Dec 31, 2025

Celebrate New Year’s Eve in Ocean City with a spectacular fireworks display by the sea! Ring in the new year with vibrant lights, music, and festive fun.

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