Fall in 2019 Events in Ocean City

As back to school season begins and post-summer withdrawal symptoms begin to set in, you’re probably wishing you could go back to the beach.

Good news: you can!

September marks the beginning of Ocean City, Maryland’s “second season.” The beaches are less crowded and there are still plenty of things to do with your family and friends. To help you ring in the fall, we’ve rounded up a few popular festivals and activities happening in Ocean City.

After long days packed with fun, you’re going to want to retreat to a comfortable rental where you can unwind and enjoy crisp fall breezes. Check out all of Vantage’s current options to find your place near the action.


Celebrate the end of the summer season at Sunfest Weekend, Sept. 24-27 in Ocean City, MD.

Celebrate the end of the summer season at Sunfest.

For the 45th year, Sunfest is lighting up Ocean City, MD. This free, family-friendly, four-day festival features wall-to-wall entertainment. From September 19 to 22, Ocean City’s Inlet Parking Lot becomes a sprawling sea of tents full of arts and crafts, delicious food and live music.

Artisans are the heart of Sunfest. Hand-blown glass, wood carvings, jewelry, tchotchkes and trinkets abound at the 180 vendor stands. Be sure to check out another Sunfest highlight—the Kite Festival on the beach, where you’ll see spectacular displays by master kite flyers, kite-making workshops and intense aerial duels.

On top of all that, you can get down all day long to live music. In addition to the free daytime performances, Sunfest offers ticketed headlining events. This year’s headliners are tribute band Who’s Bad: The Ultimate Michael Jackson Experience, Texas-born country singer Granger Smith with his alter ego “Earl Dibbles, Jr.” and New Orleans jazz band legend Trombone Shorty with Orleans Avenue.

Wine on the Beach

September 27 and 28 during the 25th annual Maryland Wine on the Beach Festival, aka Wine Fest.

Fun in the Ocean City Inlet continues September 27 and 28 during the 25th annual Maryland Wine on the Beach Festival, aka Wine Fest. Featuring over a dozen Maryland vineyards as well as local breweries, this libation celebration gives you and your friends an opportunity to learn about Maryland wines, sample new beverages and bring home some bottles for your collection. You can sip these new additions from your commemorative wine glass, included with admission!

Wine Fest isn’t just about wine. Over 30 vendors are slated to offer everything from wood carvings crafted from Chesapeake Bay driftwood to gourmet pretzels and custom laser engravings. It all pairs perfectly with the daily live music from local bands like Maryland Entertainment Hall of Famer Pat O’Brennan, regional band Three Penny Opera and Eastern Shore honky-tonkers Bird Dog and The Road Kings.

Powerboat Grand Prix

Each year, spectators flock to Ocean City’s beaches to witness dozens of boats roaring from shoreline to finish line. The Powerboat Grand Prix, presented by the Offshore Powerboat Association, makes wakes this year with races on Sunday, September 29 between 1st and 18th Streets.

Miles of beach will be reserved for you to check out the 4,000-horsepower boats as they zoom by at lightning-fast speeds. It’s estimated that about 20 boats will take part in each race. The action starts at noon and is free to the public.

Stop by the Race Village the day before and enjoy food and music while the boats are inspected and tested on the water.

Family Bonfire on the Beach

You can make s’mores, drink hot chocolate and listen to stories and music around a toasty bonfire in the sand.

Want a perfect combination of fall activities and a summer environment? Bring your beach chairs and cozy blankets to the 130th Street Beach on the evening of October 4. You can make s’mores, drink hot chocolate and listen to stories and music around a toasty bonfire in the sand.

Island Wine Fall Fest

Enjoy gourmet hors d’oeuvres and oysters on the half shell.

Island Wine Fall Fest on Fager’s Island is back by popular demand for its second year.  On October 5 from noon to 4:00 p.m., come sample everything from Fager’s Island wine to craft beers and ciders. Enjoy gourmet hors d’oeuvres and oysters on the half shell. And take home your very own souvenir tasting glass to commemorate the event.

Endless Summer Cruisin

Endless Summer Cruisin in Ocean City, MD
Endless Summer Cruisin in Ocean City, MD

From October 10 to 13, the Inlet lot and Ocean City Convention Center will transform into a showcase for over 2,000 cars participating in Endless Summer Cruisin. This is no ordinary automotive show. You’ll find every kind of tricked out vehicle you can imagine. Dance to the sounds of the Doo Wop Project and watch the cars roll by during several different parades.

Spooktacular Surf Stomp

There are plenty of tricks and treats at this amateur surfing competition hosted by the Eastern Surfing Association (ESA). Surfers of all skill levels are invited to drop in to Assateague Island on October 12 and compete. It’s a terrific scene for spectators as well. This will be ESA’s sixth and final surfing contest of the year, so don’t miss out.

Historic House Tour

You can learn a lot about Ocean City’s rich history by visiting some of its oldest establishments. The Second Annual Historic House Tour lets you do just that on October 12 from 10:00 a.m. to 4:00 p.m. Journey on a trip back in time courtesy of the Ocean City Museum Society with insights into the architecture and stories behind the longstanding houses and churches.

Ocean City Restaurant Week

Restaurant Week runs two weeks,
from October 13 through 27.

Experience the many savory and sweet flavors of Ocean City, Maryland, during Restaurant Week. Because you can’t have too much of a great thing, this year’s event actually runs two weeks, from October 13 through 27. Participating eateries will have fixed menus prepared special in addition to their standard offerings. It’s the perfect time to visit a favorite restaurant or try something new. Reservations are highly recommended.

Harbor Day at the Docks 

On Saturday, October 19, the free Harbor Day maritime heritage festival celebrates Ocean City’s storied history and traditions on the West Ocean City Commercial Harbor. Bring the whole family to watch chefs cook your favorite seafood dishes, compete in crab picking contests, explore special educational exhibits and more.

O.C.toberfest Beach Maze

You never know what’s lurking inside the labyrinth!

Ghouls and goblins of all ages are invited to this free, fun, Halloween-themed maze on the beach. You never know what’s lurking inside the labyrinth, so enter at your own risk! The maze will be open on the weekends of October 19 and 20 and 26 and 27 at North Division St. and the Boardwalk.

Seaside 10 Mile/5K Halloween Run

Throw on your most outrageous costume and dash over to the Inlet lot on October 26 for OC Tri-Running Sports’ 10 Miler or the 5K. These festive, family-friendly runs will certainly make your heart race. The 10 Miler begins at 9:00 a.m. and the 5K starts shortly after at 9:15 a.m.

Shore Craft Beer Fest

Unlimited tastings of more than 40 beers from 16 breweries.

Offering unlimited tastings of more than 40 beers from 16 breweries, Shore Craft Beer Fest is sure to brighten your day at Sunset Park. Come see what all the buzz is about October 26 from 12:30 to 4:30 p.m. This is a kid- and pet-friendly festival, with food trucks, vendors and lots of great live music.

Shell Shocked

This event combines two Ocean City favorites: eating oysters on the half shell while drinking tasty craft beer. Come to Fager’s Island on November 2 and 9 with your friends and family (over 21, of course) for an amazing time. The menu also includes barbecue ribs, chicken and other dishes, and different live musicians perform each day.

Winterfest of Lights

Winterfest of Lights in Ocean City, MD

Winterfest of Lights in Ocean City, MD

Starting November 21 and lasting through the end of the year, Northside Park will be adorned with over 1,000,000 dazzling lights. Animated displays, a heated pavilion and a 50-foot-tall Christmas tree help make Winterfest of Lights the ultimate holiday exhibition. Take a trip on the Winterfest Express—a mile-long journey through 58 acres of light displays with a fairytale theme.

Light Up Downtown Winter Festival

See the Boardwalk at the Inlet become a true winter wonderland on Saturday, November 23. This free, spectacular light show gives you the opportunity to buy presents for the upcoming holiday season while your kids play fun games and win prizes. Don’t forget about a photo op with Santa!

Comic Con

Assemble your squad on December 14 and join other fans of comics, cosplay, anime, video games and art at the Roland E. Powell Convention Center for Ocean City’s Comic Con! The Delaware Anime Society will sponsor anime screenings throughout the day. Compete in the cosplay contest, sit in on riveting panels and meet the artists behind your favorite works.

More reasons to fall in love with Ocean City

Let the Vantage team help you plan a memorable fall getaway to Ocean City, Maryland.   

Autumn in Ocean City is far less crowded but no less fun. Adding to the allure: You can book a fantastic rental property at off-season rates. Let the Vantage team help you plan a memorable fall getaway to Ocean City, Maryland.   

It’s easy to browse and book direct at www.VantageOceanCity.com. You can also contact our friendly reservation specialists at 410-723-2002 for help. Remember to book direct through Vantage—that’s how you get the lowest possible rates and the best possible selection.

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About Vantage

Founded in 2007, Vantage Vacation Rentals specializes in delivering exceptional experiences for both vacation property owners and their rental guests in popular Maryland destinations such as Ocean City, Annapolis and the Eastern Shore of the Chesapeake Bay, as well as the Delaware beaches and North Myrtle Beach, South Carolina. Vantage serves owners with extensive property marketing and promotion as well as comprehensive property management services to help maximize rental income opportunities. With over 550 managed properties, Vantage makes it easy for vacationing guests to find and reserve the perfect option—then enhances their stay with exclusive benefits and discounts. To learn more about Vantage Vacation Rentals, visit VantageOceanCity.com, EasternShoreVacations.com and VantageMB.com.