10/01/2026 to 10/29/2026 - Thursdays in October! Play to win your share of $2,000 CASH! Registration: 5PM-7PM • Tournament Begins: 7PM Entry fee $25 per person. Limited to the first 48 registrants.

10/22/2026 to 10/22/2026 - With over 700 shows across 38 states and international sold-out crowds under their belt, Elton Dan & The Rocket Band are bringing their explosive, infectious energy to Ocean City. This isn't just an

10/22/2026 to 10/25/2026 - Join us under the big top tents for four days of great music, arts and crafts, delicious food, kid-friendly activities, tractor rides, craft beer, the Halloween Beach Maze, Howl-O-Ween Pet Parade,

10/23/2026 to 10/23/2026 - Celebrate the music of Paul McCartney with a dynamic, full multimedia concert production that sets the gold standard for tribute performances. Starring Tony Kishman—a veteran of the Broadway smash hit

10/19/2026 to 10/23/2026 - If you live on the Delmarva Peninsula, stop by and enjoy the museum free of charge! Locals Week in Ocean City, Maryland, is hosted annually by the Ocean City Museum Society and occurs in the fall.

10/23/2026 to 10/25/2026 - The Premier Home & Artisan Expo will be held in the R.E. Powell Ocean City Convention Center from 10am - 4pm on Friday, October 23rd, Saturday, October 24th, and Sunday, October 25th 2026.The HOME

10/23/2026 to 10/23/2026 - Join historian, storyteller, and magician David Dellman for an unforgettable evening where the fascinating history of Ocean City comes to life through incredible magic, captivating storytelling, and

10/23/2026 to 10/24/2026 - Wine on the Beach, the beloved annual summer festival celebrating the regional industry, will be returning to the Ocean City Inlet October 23-24, this year as part of Sunfest! Located inside the

10/24/2026 to 10/24/2026 - Mark your calendars... our Fall Market is happening on Saturday, October 24th from 10 AM–2 PM at The Modern Graze! We're so excited to bring together an amazing group of local makers, artisans,

10/24/2026 to 10/24/2026 - Wrap up your Sunfest weekend with a polished, timeless evening built around the music of Michael Bublé and the Great American Songbook that inspired his career. Fronted by the exceptionally

10/24/2026 to 10/24/2026 - This spooky annual bash for Halloween includes a best trick contest with prizes and music. There will also be prizes for best costumer, so dress in your spooky skater style! All participants must be

10/24/2026 to 10/24/2026 - A walk on the boardwalk to support breast cancer survivors and remember those we have lost. Funds raised from this event go to the American Cancer Society to fund research and patient support.

10/10/2026 to 10/31/2026 - Learn the history, feel the mystery, and maybe encounter a spirit or two that still lurk at most of the properties on the tour. The historic district of Ocean City is currently active with ghosts of

10/24/2026 to 10/24/2026 - OCtoberfest is back in October! Shore Craft Beer’s waterfront craft beverage festival returns to Ocean City, Maryland, on Saturday, October 24, 2026, during Sunfest weekend.The 12th annual Ocean City

10/25/2026 to 10/25/2026 - Celebrate Halloween with a fun-filled, family-friendly event for all ages! Wander through our inflatable corn maze, enjoy festive carnival games like ring toss, pumpkin bowling, and darts, and snap

10/25/2026 to 10/25/2026 - Bring your fur babies and join us at the Shore Deck at Ashore Oceanfront Hotel in Ocean City on Sunday, October 25, from noon to 3 p.m. for an afternoon of fun, prizes, food and adorable adoptable

10/25/2026 to 10/25/2026 - Meet Adoptable Pets from Worcester County Humane Society. All proceeds from this event goes to them. Find your new best friend while supporting a great cause! Bring your furry friends to Ashore! Join

10/25/2026 to 10/25/2026 - Our Kitchen, Our Stories: Heritage, Family & Recipes Sunday, October 25 | 1–3:30 PMArt League of Ocean City Join us for a special afternoon celebrating the recipes, stories, and traditions passed down

10/06/2026 to 10/27/2026 - Saturdays, Sundays, and WednesdaysOctober 3rd-28th 4PM-8PM Every hour, five Club Ocean Members actively playing with their card will be selected to play a game in the Prize Zone to win CASH or FREE

10/06/2026 to 10/27/2026 - Tuesdays in October • 4PM-7PM Win your share of $2,000 Free Play! One FREE Entry, plus every 150 points = one additional entry. Play up to five times every Tuesday. Must be in line by 7:05PM to

07/07/2026 to 11/24/2026 - 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

10/29/2026 to 10/29/2026 - Everyone’s favorite Scottish nanny is headed to Ocean City, Maryland in this internationally acclaimed hit musical critics call “wonderful, heart-warming, and laugh-out-loud funny” (Manchester Evening

10/29/2026 to 11/01/2026 - Where Weekends Begin.The OC RV & Van Lifestyle Show is more than an RV show. It’s Ocean City’s largest outdoor lifestyle show, bringing together RVs, custom vans, camping, overlanding, off-road

10/30/2026 to 11/01/2026 - **Bronco Beach Bash Ocean City** returns to Ocean City, Maryland, October 30 – November 1, 2026, bringing together hundreds of Ford Bronco owners and off-road enthusiasts from across the Mid-Atlantic

10/30/2026 to 10/30/2026 - David Anthony - Hypnotist Show @ Ocean Downs! 21 years of age or older are welcome! Doors: 7PM • Showtime: 8PM General Admission Seating is first-come, first-served. Taxes and fees may apply.

10/30/2026 to 10/30/2026 - Brew up a Big Win! Friday, October 30th • 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.

10/31/2026 to 10/31/2026 - Saturday, October 31st • 7PM-10PM One Winner Every Hour! Earn Entries October 1st-31st, every 10 points = one entry. Plus, earn 3x Entries on Thursdays!

10/31/2026 to 10/31/2026 - Get ready for a frightfully fun and creative Halloween at the Art League of Ocean City! Join us on Saturday, October 31 from 11 AM–1 PM for a FREE Halloween Celebration filled with spooky, hands-on

11/01/2026 to 11/01/2026 - Rumours of Fleetwood Mac, the world’s finest tribute to Fleetwood Mac, returns to the stage celebrating the very best of Fleetwood Mac. Channeling the spirit of Fleetwood Mac at their very best,

06/05/2026 to 12/04/2026 - Join us for a special First Friday Block Party! Meet the artists, enjoy complimentary hors d'oeuvres, explore inspiring new exhibitions, and spend the evening celebrating art and community at the