The summer crowds have gone home, the ocean air has a little bite to it, and the boardwalk finally has room to breathe. Then, for one weekend in late October, the whole town fills right back up.

Sunfest runs October 22 to 25, 2026, and Wine on the Beach pours October 23 and 24. Both happen at the Inlet, at the south end of the boardwalk, which puts them a short walk from Americana Resorts. Add a Halloween weekend, a ghost tour, and a full lineup of shows at the Performing Arts Center, and you have one of the best weekends of the year to visit Ocean City, MD.

Here’s what’s happening and how to plan your stay.

Sunfest at the Inlet (October 22 to 25, 2026)

Sunfest is Ocean City’s big end-of-season party, and locals and repeat visitors plan their fall around it. Large heated tents go up in the Inlet lot and fill with craft vendors, artists, food stands, and live music for four days.

Come hungry. Crab cakes, funnel cake, kettle corn, and fresh-cut fries are all part of the experience. If you’re starting your holiday shopping early, the craft tents are a great place to find handmade gifts you won’t see anywhere else.

Since Sunfest sits right at the end of the boardwalk, you can leave the car parked at the hotel and walk over. That alone saves you the hardest part of the weekend: finding a parking spot near the Inlet.

Wine on the Beach (October 23 and 24, 2026)

The same weekend, Wine on the Beach sets up in the Inlet lot with wine tastings, food, and music by the water. It’s an easy add-on to a Sunfest day: browse the craft tents in the morning, then wander over for an afternoon of tastings.

More Ocean City, MD Weekend Activities

Sunfest weekend overlaps with the start of Halloween season, so there’s plenty to fill the rest of your trip.

• Ocean City Ghost Tour (Saturdays through October 31). Tours start at the Inlet end of the boardwalk, close to the hotels. Hear the town’s spookier stories after dark.
• Making Strides Against Breast Cancer (October 24). The walk takes place on the boardwalk at the Inlet. Join in or cheer on the walkers before breakfast.
• Shore Craft Beer OCtoberfest (October 24). Craft beer and fall flavors at Cambria Ocean City, a good pick for anyone who’d rather skip the wine.
• Premier Home & Artisan Expo (October 23 to 25). Home ideas, local makers, and artisans at the Convention Center.
• Halloween “Spook Out” Party (October 25). A family Halloween party at Northside Park. Let the kids wear their costumes early.
• Halloween Bowl Bash (October 24). A Halloween skate event at the Ocean Bowl Skate Park.

A Night Out at the Performing Arts Center

Ocean City’s new 1,200-seat Performing Arts Center has a busy fall lineup, which makes it easy to turn a beach weekend into a date night. Shows around Sunfest weekend include:

• The Music Man (October 18)
• Elton Dan (October 22)
• A Paul McCartney tribute (October 23)
• A Michael Jackson tribute (October 24)
• Mrs. Doubtfire (October 29)

If you’re staying a little longer or coming back in November, a Fleetwood Mac tribute plays November 1 and the Irish Tenors perform November 27. Grab tickets early, since the tribute nights tend to sell well.

Where to Stay for Sunfest Weekend

Americana Resorts has several oceanfront options steps from the boardwalk, so you can pick the one that fits your group.

• Americana Hotel Oceanfront is the pick for chilly evenings. The indoor heated pool is open 10am to 10pm, and Hammerheads Bar & Grill is right on site for dinner after a long day at the festival.
• Americana Motor Inn Oceanfront is home to Flavours of Italy, so pizza and pasta are an elevator ride away.
• 6th Street Condos and 10th Street Condos give bigger groups full kitchens, a washer and dryer, and room to spread out.
• Cabin at the Beach is a cozy home base for a smaller crew.
• The Sunset House offers three bedrooms, a kitchen, and living room space for larger groups. 

Save on your fall stay. AARP members get 10% off starting October 13, just in time for Sunfest. Staying a few extra nights? Check the Specials page for stay-longer discounts on 3-, 5-, and 7-night hotel stays and 5- and 7-night condo stays.

Book Your Sunfest Weekend

Sunfest weekend is one of the busiest of the fall, and rooms near the Inlet go quickly. Book your stay at Americana Resorts now, walk to the festival, and come back to the ocean view at the end of the day.

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