Ocean City MD Maryland Calendar of Events and Special Events in Ocean City

lots of hands raising wine glasses in the air

September 6 `25

Wine Fest: Wine on the Beach
Local Live Music Featuring Byrd Dog, The Road Kings & Transfusion

Hugh T. Cropper Inlet Parking Lot

Maryland Wineries, more craft vendors and fine artists, and improved access to the oceanfront festival combine to make the upcoming fall classic the best by far. It promises to be the most enjoyable yet.

Wineries from Maryland, will be bringing a full range of products for festival-goers to sample and purchase -- by the glass, bottle or case. Delicious, Delmarva cuisine, micro brews and domestic beer will be available for purchase.

We improved and expanded the festival layout, Also better admission procedure promises to facilitate entrance and enhance the festival experience. Online ticket sales are offered at a reduced price, advance tickets are available on the festival website.

No pets, coolers or outside food or beverages. All bags subject to search. You may bring chairs, blankets, small tables and small umbrellas.

General admission includes a souvenir wine glass, samplings of wine, and on-stage entertainment.

$35. with photo ID
$15. (children 13 - 20)

Free under 12 years of age

Ticket Sales may not be available at the gate, advance tickets on sale at the Ocean City Convention Center or purchase online today!

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September 6 `25

The Bills

High Stakes Bar & Grill

The Bills (formerly known as Slappy Hour) is the musical collaboration of Benjamin Davis, Nathan Nasteff, and Lukas Saylor. Music for the people, from the shed to the streets. This local band is fresh out of Salisbury, Maryland and heading to play for you at High Stakes Bar and Grill, Fenwick Island Delaware. Catch Ben Davis rocking the stage while enjoying a refreshing beverage and great food!

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motorcycle with beautiful sunset in the backgroun

September 10 `25 - September 14 `25

OC Rock & Ride
Get Your Tickets Today

OC Events

OC Rock & Ride — running September 10–14, 2025 — is a bold new chapter in the legacy of Ocean City BikeFest. Rebranded and revitalized by local organizers Matthew and Tyler Odachowski, this rally embraces the traditions that riders cherish while introducing modern touches to elevate the experience. Hosted at Ocean City’s scenic Inlet (809 South Atlantic Avenue, Ocean City, MD 21842) and the Roland E. Powell Convention Center (4001 Coastal Highway, Ocean City, MD 21842), the event features live music, custom motorcycle displays, vendor fairs, charity rides, poker runs, factory demos, stunt shows, and more.

Get your OC BikeFest tickets today, this rally is going to be epic!

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September 10 `25

Balkan Party

Purple Moose Saloon

Go to The Purple Moose Saloon on the Boardwalk in Ocean City, Maryland Boardwalk or the original Balkan Party every Wednesday night... if YOU KNOW, YOU KNOW! See you there!

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September 12 `25 - September 13 `25

Phil Perdue - "The Piano Man"

Captain's Table Restaurant and Bar

Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland. Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.

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Silver Microphone colorful lights in the background

September 12 `25

Live Music at Buxy's Salty Dog Saloon
Featuring Johnyy Cardo

Buxy's Salty Dog Saloon

Buxy's Salty Dog, your home away from Pittsburgh presents live music all year long ! Enjoy your summer nights with our crew and be sure to check out our awesome food and drink specials. We are open every day at 11am and look forward to seeing you soon!

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lots of smiling and dancing girls having fun

September 12 `25 - September 13 `25

Surreal

Purple Moose Saloon

Surreal is one of the most popular classic rock bands in the Mid-Atlantic area. Exceptional musical talent, skilled precision, soaring four part vocal harmonies, dynamic personalities, awesome song list and professional sound, lighting and stage production is guaranteed to please a wide variety of classic rock fans everywhere they perform, with a highly entertaining and high energy live show that truly delivers, night after night.

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September 17 `25

Balkan Party

Purple Moose Saloon

Go to The Purple Moose Saloon on the Boardwalk in Ocean City, Maryland Boardwalk or the original Balkan Party every Wednesday night... if YOU KNOW, YOU KNOW! See you there!

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September 19 `25 - September 20 `25

Phil Perdue - "The Piano Man"

Captain's Table Restaurant and Bar

Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland. Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.

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September 19 `25

Live Music at Buxy's Salty Dog Saloon
Featuring Full Circle

Buxy's Salty Dog Saloon

Buxy's Salty Dog, your home away from Pittsburgh presents live music all year long ! Enjoy your summer nights with our crew and be sure to check out our awesome food and drink specials. We are open every day at 11am and look forward to seeing you soon!

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September 20 `25

Black Dog Alley

High Stakes Bar & Grill

Black Dog Alley whose mission is to move you, to groove you and to rock your very soul is playing live at High Stakes Bar and Grill in Fenwick Island tonight. This Easton, MD based band has a diverse set list ranging from classic jam rock and rhythm and blues, to funk and reggae.

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September 24 `25

Balkan Party

Purple Moose Saloon

Go to The Purple Moose Saloon on the Boardwalk in Ocean City, Maryland Boardwalk or the original Balkan Party every Wednesday night... if YOU KNOW, YOU KNOW! See you there!

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September 26 `25 - September 27 `25

Phil Perdue - "The Piano Man"

Captain's Table Restaurant and Bar

Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland. Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.

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September 26 `25

Live Music at Buxy's Salty Dog Saloon
Featuring Muskrat Lightning

Buxy's Salty Dog Saloon

Buxy's Salty Dog, your home away from Pittsburgh presents live music all year long ! Enjoy your summer nights with our crew and be sure to check out our awesome food and drink specials. We are open every day at 11am and look forward to seeing you soon!

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September 27 `25

Live Music at Buxy's Salty Dog Saloon
Featuring Aaron Howell

Buxy's Salty Dog Saloon

Buxy's Salty Dog, your home away from Pittsburgh presents live music all year long ! Enjoy your summer nights with our crew and be sure to check out our awesome food and drink specials. We are open every day at 11am and look forward to seeing you soon!

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electric guitar being played at an angle in B&W

September 27 `25

Dust N' Bones

High Stakes Bar & Grill

Come to High Stakes Bar and Grill in Fenwick Island, DE to hear live entertainment. Listen to musicians playing with the talented artists - Dust N' Bones. This should be a great night of entertainment!

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October 1 `25

Balkan Party

Purple Moose Saloon

Go to The Purple Moose Saloon on the Boardwalk in Ocean City, Maryland Boardwalk or the original Balkan Party every Wednesday night... if YOU KNOW, YOU KNOW! See you there!

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October 3 `25 - October 4 `25

Phil Perdue - "The Piano Man"

Captain's Table Restaurant and Bar

Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland. Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.

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October 4 `25

Monkee Paw

High Stakes Bar & Grill

Catch Monkee Paw at High Stakes Bar & Grille in Fenwick Island, Delaware! Monkee Paw's musical style ranges from duo to quartet, and they have spent almost a decade performing in Fenwick and Ocean City. Spanning a wide variety of genres, with a strong focus on vocal harmony. Band members include: Mike Givens, Rick Smith, Joseph Wirt, Ray Perrone, Dean Haemel and Adam Ask.

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October 8 `25

Balkan Party

Purple Moose Saloon

Go to The Purple Moose Saloon on the Boardwalk in Ocean City, Maryland Boardwalk or the original Balkan Party every Wednesday night... if YOU KNOW, YOU KNOW! See you there!

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October 10 `25 - October 11 `25

Phil Perdue - "The Piano Man"

Captain's Table Restaurant and Bar

Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland. Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.

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October 15 `25

Balkan Party

Purple Moose Saloon

Go to The Purple Moose Saloon on the Boardwalk in Ocean City, Maryland Boardwalk or the original Balkan Party every Wednesday night... if YOU KNOW, YOU KNOW! See you there!

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October 17 `25 - October 18 `25

Phil Perdue - "The Piano Man"

Captain's Table Restaurant and Bar

Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland. Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.

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man plays a brown acoustic guitar at a 45 degree angle

October 18 `25

Rick & Lennon La Ricci

High Stakes Bar & Grill

It is rare to find a father-son musician duo performing in the Ocean City and Delaware Beaches area. Ricky and Lennon LaRicci are one very popular duo.

Rick and Lennon play at venues all over the Ocean City area as well as “back home” in Baltimore. Here’s a unique quote from Lennon’s website: “Along the way bandmates have come and gone, but what still remains is Rick and his son Lennon doing what they love everyday…playing music.”

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