11/06/2026 to 12/18/2026 - Enjoy live music every Friday from 8pm-11pm in the Playbook Sports Bar! FRIDAYS 8PM NOVEMBER 6: DUST N' BONES NOVEMBER 13: VOODOO TRIBE NOVEMBER 20: FUZZBOX PIRANHA NOVEMBER 27: BRYAN SCAR DECEMBER

11/14/2026 to 11/14/2026 - Complete your foot tour of Maryland with the Ocean City Running Festival! YEAR FOUR of this event will feature scenic routes, all of which include the OC Boardwalk, with some courses taking you to

11/14/2026 to 11/14/2026 - Unleash your inner magician in this fun and accessible magic class! Learn the secrets behind some of the classics of magic, including card magic, rope magic, and mind reading. Develop stage presence,

11/03/2026 to 12/29/2026 - Reel In The Biggest Trivia Prizes Around. Tuesdays at The Playbook Sports Bar • Sign-up: 6:30PM Game Time: 7PM! Play for a chance to win FREE PLAY! 1st – $250 FREE PLAY 2nd – $100 FREE PLAY 3rd – $75

11/18/2026 to 11/18/2026 - ittle Arty's Art and Storytime Date: November 18, 2026 Time: 10:00 - 11:00 Cost: FREE Join Essence and Mary Anne for Little Arty's Art and Storytime at the Art League of Ocean City. This is a

11/18/2026 to 11/18/2026 - Originals Only: No Covers, Just Creators is a celebration of authentic, original expression across all creative mediums. Poets, comedians, musicians, and performers come together to share their unique

11/19/2026 to 12/31/2026 - Get ready to embark on a journey into the enchanting spirit of the holiday season at the 2026 Winterfest of Lights in Ocean City, MD. Enjoy a walk-through winter wonderland experience and explore the

11/19/2026 to 11/19/2026 - Kick off the holiday season in Ocean City as we celebrate the opening night of Winterfest of Lights on Thursday, November 19! Join us for a magical evening featuring a festive performance by the

11/21/2026 to 11/21/2026 - Saturday, November 21st 2PM – 6PM Donate $20 to spin the wheel to win Free Play! All proceeds benefitting: Worcester Goes Purple! One spin per person.

10/19/2026 to 11/23/2026 - Bull on the Beach 94th street will be hosting trivia with Ole Chap Trivia on Monday nights starting at 6:30PM. Trivia will be hosted in our bar area, so everyone must be 21+

11/26/2026 to 11/26/2026 - Looking for another great spot to enjoy Thanksgiving dinner without the stress of preparing a feast at home? Marlin Moon is ready to welcome guests for a holiday gathering filled with good food and

11/26/2026 to 11/26/2026 - If you’re looking for a more traditional sit-down dining experience this Thanksgiving, 32 Palm is serving up a special holiday meal designed to make the occasion feel extra memorable. For $55 per

11/27/2026 to 11/28/2026 - 🎢 Trimper Rides Christmas Carnival 🎢🎄 The holiday magic is coming to Trimper Rides! Join us for TWO days of festive family fun, exciting rides, and our BIGGEST pass savings of the year! 🎅 📅

11/27/2026 to 11/29/2026 - Join us for the 44th Annual Holiday Shoppers Fair! As soon as Thanksgiving wraps up, the Ocean City Convention Center comes alive for holiday shopping with the weekend-long Holiday Shopper’s Fair!

11/27/2026 to 11/27/2026 - Join us 5pm – 8pm as we begin the holiday season featuring beautifully carved Ice Sculptures sponsored by the Berlin businesses! 30+ Holiday themed lighted sculpturesTree is lit at 6pm Greet Santa at

11/27/2026 to 11/27/2026 - Since their explosive 1998 PBS debut, The Irish Tenors have reigned as the undisputed "Celtic Music Kings." With ten best-selling albums and a legacy that rivals icons like The Three Tenors and Andrea

11/27/2026 to 11/27/2026 - 🎢🎁 TRIMPER RIDES BLACK FRIDAY SALE! 🎁🎢 🛍️ IN-PERSON & ONLINE! Our BIGGEST pass savings of the year are BACK! Give the gift of FUN this holiday season with two days of incredible deals on your

11/27/2026 to 11/27/2026 - Friday, November 27th 8am – Midnight Club Ocean members who earn 150 points can swipe at the kiosk to play the game to win Free Play! Play up to 10 times

11/28/2026 to 11/28/2026 - 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

11/28/2026 to 12/12/2026 - Brunch & Craft with our friends from the North Pole!Saturdays Starting 11/28 from 10am - Noon(11/28, 12/5, 12/12) Tickets Include: Access to the park (self-guided tour) and Kangaroo Walkabout Build

12/03/2026 to 12/03/2026 - 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

06/05/2026 to 12/04/2026 - First Friday Opening Reception Friday, November 6, 2026Time: 5:00–7:00 PMLocation: Art League of Ocean City502 94th Street, Ocean City, MDAdmission: FREE & Open to All! Join us for our November First

12/04/2026 to 12/04/2026 - Friday, December 4, 20266-10pmRoland E Powell Convention Center4001 Coastal Highway – Ocean City Tickets $150 Dress Code: Black Tie Optional Greeted by red carpet and champagne, enter this magical

12/05/2026 to 12/05/2026 - The Holiday season is almost here and Ocean City isn’t skipping a beat for 2026. The Ocean City Christmas Parade goes in-house this year to continue the 43 year tradition started by Gold Coast

12/05/2026 to 12/05/2026 - Step into the magic of a colonial Christmas at Rackliffe House!Join us for two afternoons of candlelight house tours, local artisan shopping, and holiday cheer in this beautifully restored

12/05/2026 to 12/12/2026 - Step into the town that is "Cool and Fun" by day and known for "The Walking Dead" at night. So many ghosts, spirits, and even an Elemental still lurk in the dark streets of Berlin. - just 15 minutes

12/06/2026 to 12/06/2026 - A Morning Filled With Holiday Magic Bring the whole family and enjoy a delightful breakfast while spending some special time with everyone’s favorite Christmas visitor… Santa Claus himself! Kids will

12/06/2026 to 12/06/2026 - Check back later this year for details!

12/10/2026 to 12/10/2026 - Join us as we celebrate Hanukkah at the Inn Berlin at 4:00pmWe Light the Menorah – 5:00pmThe Inn Berlin is located at 15 Harrison St Berlin MD next to the Berlin Library.

12/10/2026 to 12/10/2026 - “A Blue Christmas” is Jesse Garron’s heartwarming holiday tribute that brings Elvis Presley’s festive spirit to life. Featuring beloved hits like “Blue Christmas,” “Santa Claus Is Back in Town,” If