Entertainment & Events in Ocean City, MD (and surrounding areas)

Character Breakfast

At Roland E. Powell Convention Center. Date: Saturday, November 28, 2025 Times: 9-11am Location: Ocean City Convention Center (4001 Coastal Hwy, Ocean City, MD 21842), Upstairs Ballroom Kick off the holiday season with a morning full of

Shortcut Sunny

Homestead Bluegrass

Union Road Duo

Full Circle

Hideaway x Area 51 Pop Up

Hideaway Area 51 Pop-Ups are BACK for a second year this off-season! While Hideaway may be a seasonal, outdoor restaurant, we’re bringing a little piece of it inside to Area 51, located right in front of Hideaway. Expect a limited Hideaway menu, the same atmosphere and views you love, and a cozier setup perfect for the colder months. Mark your calendars for our 2026–2027 pop-up dates: November 27 & 28 January 1 & 2 🥂 February 12, 13 & 14 ❤️ March 19 & 20 April 16 & 17 Reserve Your Table Now! A…

Tranzfusion

On the Deck — live rock music, for DelMarVa, and beyond

Rick & Lennon la Ricci

Permilla Project

DJ Connair in Morley Hall

DJ E-State Live at Tiki Stage

DJ E-STATE, an Eastern Shore native, has been a driving force in the regional music scene. Holding prestigious residencies at various venues, E-STATE crafts dynamic sets that seamlessly blend different genres into unique live musical experiences. Notably, E-STATE has showcased their versatile craft at high-profile events, including the United States Air Force Ball. E-STATE takes pride in highly technical transitions and blends, ensuring an unforgettable experience for the crowd. E-STATE not onl…

Muskrat Lightning

DJ Robcee

On the Deck — OC nightlife veteran WITH OVER 3 DECADES OF DJ EXPERIENCE playing A SEAMLESS MIX OF dance and party music

The Event Horizon

One of New Jersey’s top club bands, and fast becoming one of the Northeast’s biggest acts, we thrive on the diversity of the wide variety of the musical taste of today’s individuals. Let’s face it… people today are into much more of a musical variety than ever before. From Rock to Pop to Country to Dance to Hip Hop, a night with The Event Horizon has it all. The incredible vibe and relentless energy of the bands performance, coupled with a state of the art stage production, make for an unparall…

NFL Sundays

Trivia Night

Sign in 5:30 Prizes Specials All ages

Bar Bingo!

Tuesdays 6-8 PM in the bar with DJ Rupe Free to play Food & Drink Specials 21+ to Play Win Prizes!

Trivia Night with TNT Games

Shortcut Sunny

Cecilia Grace

Berlin Christmas Parade

At Downtown Berlin, Main Street. 80+ Floats, Dancers, Firetrucks, Santa and More! Join us for the largest holiday parade on the Eastern Shore. Parade starts at 7pm at The Berlin Welcome Center, then runs north to the Berlin Fire

Keith White Duo

Hanukkah Celebration at The Inn Berlin

At Downtown Berlin, Main Street. Join us as we celebrate Hanukkah at the Inn Berlin at 4:00pm We Light the Menorah – 5:00pm The Inn Berlin is located at 15 Harrison St Berlin MD next to the Berlin Library.

Fun Fridays with Lauren Glick

🎶 Friday Nights = Live Music at The Restaurant at Lighthouse Sound! 🎶 Join us every Friday in our lounge for live music from 5–8 PM. Come early and enjoy Happy Hour food and drink specials from 4–6 PM, then stay for a great night of music, drinks, and good company. Grab your friends and make it your new Friday tradition! 🍻🎸

Ice Ice Berlin & Tree Lighting

At Downtown Berlin, Main Street. Join us 5pm – 8pm as we begin the holiday season featuring beautifully carved Ice Sculptures sponsored by the Berlin businesses! 30+ Holiday themed lighted sculptures Tree is lit at 6pm Greet Santa at

Pineapple Band

On the Deck — Blues, rock, funk, jazz cover band from Baltimore, MD.

Winter Gala

At Roland E. Powell Convention Center. Friday, December 4, 2026 6-10pm Roland E Powell Convention Center 4001 Coastal Highway – Ocean City Tickets $150 Dress Code: Black Tie Optional Greeted by red carpet and champagne, enter this magical

DJ Davie Live in Tiki