October Events in Ocean City, MD

Dog in a halloween costume with plastic pumpkins

The month of October holds some of our favorite events in Ocean City, MD and here at Hileman Real Estate, we can’t wait to share them with you! For locals and visitors alike, there’s something for everyone to enjoy on the calendar.

History buffs, pet lovers, Halloween fanatics, and people of all ages have plenty to look forward to with the October events in Ocean City. With this lineup of activities, it’s easy to see why October is one of the very best months to visit our beach town!

Visiting OCMD in October

Ocean City History Week 

Join us in appreciating our beach town with the events and activities at the Ocean City Life-Saving Station Museum. From October 10th to 16th the events will be highlighting Ocean City’s unique coastal history. The week kicks off strong with a historic house tour, exploring the history of old homes, churches, and establishments around town, with FREE admission for all Delmarva locals.

Harbor Day at the Docks

On October 16th, celebrate the maritime culture of Ocean City through Harbor Day at the Docks. The all-ages event is from 10 AM to 5 PM and includes fun entertainment like boat tours, local artisans and vendors, fresh food, live music, free kids activities, cooking demos, and more. 

OC Pet Expo

The Ocean City Pet Expo is a fun weekend experience for the whole family! Bring all your furry friends, but make sure they’re on a non-retractable leash at all times. From October 22nd to 24th, come to the Convention Center for pet products & services galore, a small animal petting zoo, pet costume, and talent contests, as well as pony rides. Get your pet into the Halloween spirit with the Howl-O-Ween Pet Parade on the 23rd!


Ocean City knows how to celebrate Halloween with an abundance of festivities on October 23rd and 24th. The 7th annual autumn Shore Craft Beer Fest will be taking place for you to enjoy delicious brews and entertainment. Stop by the popular O.C.toberfest Beach Maze over the weekend and participate in Drive & Disguise/Trunk or Treat on Saturday. End the night with a drive-in movie feature of Casper. Then, come back on Sunday for the Great Pumpkin Race and Big Toys on the Boardwalk

Looking for your spot to stay or a permanent home on Eastern Shore to celebrate all the upcoming festivities? Contact Hileman Real Estate today for spook-tacular service!