10/08/2026 to 10/11/2026 - Cruise on down to Ocean City, Maryland for the 29th Annual Endless Summer Cruisin' Car Show! Featuring over 3,000 hot rods, customs, classics and more with car shows at the OC Convention Center and

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.

10/08/2026 to 10/08/2026 - From boot-stomping honky-tonk hits to powerful patriotic anthems, this high-energy concert delivers the soundtrack of a generation. Experience live performances of the hits you know and love. Leading

10/09/2026 to 10/09/2026 - Creative Connections Free Monthly Art Club for Ages 60+ Creative Connections is designed for individuals aged 60+ who believe that creativity has no retirement date. Date: Friday, October 9Time: 11:00

10/09/2026 to 10/09/2026 - Creative Connections Free Monthly Art Club for Ages 60+ Creative Connections is designed for individuals aged 60+ who believe that creativity has no retirement date. Date: Friday, October 9Time: 11:00

10/10/2026 to 10/10/2026 - Join Us forHarbor Day at the DocksA Maritime Heritage Festival

10/10/2026 to 10/11/2026 - Announcing the OC Beach Classic XIII! October 10-11, 2026 in Ocean City, Maryland. Get more information at ocbeachultimate.com!

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

10/11/2026 to 10/11/2026 - Step back in time for a day of celebration at Rackliffe House’s Colonial Harvest Festival! 🍂 Sunday, October 11th | 11:00–4:00 (weather permitting)Join us for 250 Years of Harvest and Heritage — with

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

10/14/2026 to 10/14/2026 - Celebrate the creativity, passion, and innovation of Maryland’s small businesses at the Maryland SBDC Small Business Showcase!Meet the entrepreneurs behind the brands and shop one-of-a-kind finds,

10/16/2026 to 10/16/2026 - Come join the Ocean City Recreation and Parks Department for family fun with campfires on the beach. S’mores, hot chocolate, and water are included. WHO: Families of all sizes (pets must be leashed)

10/16/2026 to 10/17/2026 - Great event for Corvette enthusiasts and owners! Check here for more information as the event approaches.

10/17/2026 to 10/17/2026 - Participants can choose to compete (or not) in a 2-mile Walk or 5K Run at this year’s event on Saturday, October 17, at Assateague State Park.Campground day use | 6915 Stephen Decatur Hwy, Berlin,

10/17/2026 to 10/17/2026 - Come join us for our Corvette Car Show starting at 11:00 am at Jolly Roger Amusement Park at 30th St. & Coastal Highway followed by a parade of Corvettes down the Boardwalk to the Inlet Parking Lot

10/17/2026 to 10/17/2026 - OC Film Festival Horror Night: Night of the Living Dead Get into the Halloween spirit with the Ocean City Film Festival for a special Horror Night screening of George A. Romero’s iconic Night of the

10/17/2026 to 10/17/2026 - Celebrate the season at the Berlin Oktoberfest & Fall Sidewalk Sale on Saturday, October 17, from 11 a.m. to 4 p.m. in Historic Downtown Berlin. Enjoy live music, authentic Oktoberfest food, local

10/18/2026 to 10/18/2026 - There's trouble in River City when a fast-talking salesman gets his heart stolen by the town librarian. Meredith Willson's six-time, Tony Award-winning musical comedy The Music Man follows

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.

10/22/2026 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

10/23/2026 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