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

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

Trivia Night!

DJ Davie Live in Tiki

Shortcut Sunny

Union Road Duo

Social Drinking

On the Deck — Four guys were locked in their houses during the Covid-19 quarantine, unable to fulfill their destiny of playing music live. Social Drinking was born, simply as a means of fulfilling that empty space. Come get some!

The Chest Pains

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…

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