The autumn months are some of the best times to enjoy holiday magic, live music, and time with your community. Hileman Real Estate loves taking the time to highlight some of the best gatherings, fundraisers, and interesting family events available to area residents. Check out these fall and winter events in Ocean Pines, MD.
Best Halloween, Christmas, and Winter Seasonal Events Near OCMD
Halloween Fall Festival, Oct. 25, 2025
White Horse Park, 11 a.m.-2 p.m.
Join for music, a costume parade, haunted hayride and carnival games!
Halloween Spooky Swim and Swim with Santa
Sports Core Pool, Oct. 25, 2025 from 5-8 p.m. and Dec. 20 from 12-3 p.m.
Wear a suit under your costume to enter a spooky contest! Halloween crafts, games, music and food available for purchase. In December, take a swim will Jolly Old St. Nick, and enjoy crafts and games!
Ocean Pines Arts and Crafts Festival, Nov. 1, 2025
235 Ocean Parkway, from 9 a.m to 3 p.m.
Shop from local artisans and vendors.
Ocean Pines Volunteer Fire Department Bingo, Nov. 7
Ocean Pines Community Center, Cash Bingo at 6 p.m.
Join us for a fundraiser to benefit the Ocean Pines Volunteer Fire Department.
Stars, Stripes, and Stockings, Nov. 9
Ocean Pines Yacht Club Ballroom, 2-5 p.m.
Stuff a stocking to be gifted to our soldiers in time for the holiday, while enjoying live entertainment, passed hors d’oeuvres, and a cash bar.
Hometown Christmas with Santa in the Park, Nov. 29, 2025
White Horse Park, Tree Lighting at 6:30 p.m. and Santa from 7 – 8 p.m.
Enjoy a light up night filled with trees sponsored by local organizations and stay for a visit with Santa!
If you’re looking to rent or buy a home in Ocean Pines, MD, contact our team at Hileman Real Estate. One of our local agents will be happy to share their expertise with you.