The summer crowds have gone home, but Ocean City, MD has plenty going on. Between late October and mid-November, the town calendar lists more than 40 events, from Sunfest at the Inlet to Halloween parties, live shows, and the Ocean City Running Festival.
Fall is also when you can enjoy the beach and the Boardwalk with room to breathe. Here's what's happening, weekend by weekend, and how a weekend in a Central Reservations rental makes each one easier.
October 22 to 25, 2026: Sunfest Weekend
This is the busiest weekend of the fall, so book early if you want to stay close to the Inlet.
Sunfest opens Oct. 22 at the Inlet. It's Ocean City's signature fall festival, with arts and crafts vendors, festival food, and live music at the south end of the Boardwalk. The next day, Wine on the Beach pours right next door at the Inlet, so it's easy to make a full day of both.
Beer lovers can head to Shore Craft Beer OCtoberfest instead, and the Home & Artisan Expo fills the Convention Center with local makers and home ideas. If you'd like to give back while you're here, lace up for the Making Strides walk. Three tribute concerts round out the weekend, so check the town events calendar for the lineup.
Where to stay: Sunfest and Wine on the Beach are both at the Inlet. Find building comparisons to help you decide which of our buildings are closest to where you want to stay.
2026 Halloween Events in OCMD for Kids, Grown-ups and Dogs
Ocean City, MD celebrates Halloween all month long, and there are events for every age group.
The Halloween Spook Out on Oct. 25 is the family event of the season, so bring the kids in costume. Howl-O-Ween is also on Oct. 25 is all about your four-legged family. If the dog is coming along, use the Pet Friendly filter on our rental search to find a place that welcomes pets.
For something a little spookier, the Ghost Tour shares the eerie side of Ocean City's history. And from Oct. 29 to 31, Halloween events at Ocean Downs Casino give grown-ups their own version of trick-or-treat.
Why Choose an OCMD Vacation Rental
Costume changes, nap time for the little ones, and a dog who needs room to stretch out are all easier in a condo with a living room and kitchen than in a single hotel room.
Book your fall weekend with Central Reservations of Ocean City, MD
Whichever weekend you pick, a Central Reservations rental gives you more than a place to sleep.
A rental gives you more room than a hotel, with bedrooms for everyone, a living room to gather in, and a kitchen for breakfast before a race or a late snack after a show. Vacation Rental vs. Hotel in Ocean City, MD has the full comparison.
With 168 buildings to choose from, you can stay near the Inlet for Sunfest, close to the Convention Center for the expos, or somewhere quieter for a beach weekend. Get advice on choosing a location.
Pet Friendly Vacation Rentals in OCMD
Bringing the dog? Our Pet Friendly filter makes it easy to find a place for Howl-O-Ween weekend or any fall getaway. You can also leave the bulky gear at home, since beach chairs, Sand Helper motorized chairs, and baby equipment are available through Guest Services. Plus, you’ll check in at our OCMD office, where a local can assist you with anything you need during your stay.
Find your fall weekend rental with Central Reservations of Ocean City, MD.