Although we are all sad to see the summer season slipping away, there are a lot of exciting events to look forward to in the upcoming months of Autumn. Some say it’s their favorite time of the year in Ocean City! From Sunfest to Wine on the Beach to the Shore Craft Beer Festival to various Halloween activities, there’s always something for all ages.

Don’t miss out on these exciting events! Book your stay through Hileman Real Estate now!


We can’t say it enough… the weather in September and the Fall season is beautiful as the sun continues to shine and temperatures become cooler. Sunfest is the perfect way to celebrate the end of Summer while enjoying food, entertainment, and the best of Ocean City. Festival activities take place at the Ocean City Inlet, and are perfect for the whole family!

Wine on the Beach

Who doesn’t love drinking wine on the beach? Sip on different flavors and kinds of wine all day long while digging your toes in the sand! The Wine on the Beach event is a huge hit each year.

Musical Entertainment

The list could go on and on! From well-known bands like Daughtry to bands with a strong faith-based following like MercyMe, there are many concerts and performances you will not want to miss. For more details, click here.


Our fancy way of saying Octoberfest in Ocean City… from Halloween Mazes on the beach to walks and races to kid-friendly costume parties and celebrations, October is a happening month in town. Get in the Halloween spirit and experience all of the ghosts and ghouls at the beach!

Shore Craft Beer Festival

As we just mentioned… Octoberfest is an exciting time to be in town. One of our favorite Octoberfest events is the Shore Craft Beer Festival! On October 27th from 12:30 - 4:30 pm, head over to Sunset Park, overlooking the Assawoman Bay, to enjoy local brews and beautiful waterfront views! VIP Ticket holders even get shirts included in the price of their ticket and an extra hour with the brewers and the beer.

We could keep going… but we don’t want to spoil the surprise of just how fun and enjoyable Ocean City is during the Autumn season. Come see for yourself! Experience the cool fall breeze off the ocean, sip on beer and wine with unbeatable Eastern Shore views, and understand why locals love this season just as much--if not more--as Summer! Book your vacation rental for an affordable price with Hileman Real Estate today!