(Check websites for 2025 dates and times.)
Spring
The second annual Harry K Foundation Chocolate Crawl this past April was a sweet success. Thirty restaurants participated, and Sirocco walked away with the prize.
To celebrate Mardi Gras, Rehoboth Beach restaurants collaborate on the Gumbo Crawl, which sold out last April.
Each May, the Wilmington Flower Market is held in Rockford Park on the Thursday, Friday and Saturday before Mother’s Day. Sure, many come for the plants. But the beer garden, food trucks and concession stands are major perks.
Summer
The Holy Trinity Greek Festival and St. Anthony’s Italian Festival are traditionally scheduled back-to-back in June. The Greek Festival is approaching its 50th year, and food is available in the cafeteria-style dining room and the takeout booth. There are also outdoor food vendors.
Travel from Greece to Italy the following week at the St. Anthony of Padua’s Italian Festival in Wilmington’s Little Italy. Thanks to food vendors and church volunteers, the area’s Italian American heritage is on tasty display.
The Old-Fashioned Ice Cream Festival in Rockwood Park & Museum typically occurs in late June. In addition to local ice cream purveyors, there are food trucks and a beer and wine garden.
The Middletown Peach Festival, on August 17, will start with a parade and continue with a peach-pie-eating contest. Vendors will sell food, crafts—and peaches!
Before or after, head to the Wilmington Riverfront for the Beer, Bourbon & BBQ Festival, also on August 17.
Restaurants and food trucks will duke it out at the Delaware Burger Battle, scheduled for August 24 in Rockford Park. The limited-ticket event regularly sells out, and the burgers include classic creations and wacky concoctions.
Autumn
The Delaware Saengerbund’s Oktoberfest is a destination for those who can’t get enough bratwurst, weisswurst, potato pancakes, marinated herring and beer. This year’s dates are September 20–22.
In Sussex County, the Southern Delaware Wine, Food & Music Festival will move to Schellville on October 5. At this festival, you can taste food from up to 20 restaurants and sample more than 75 wines, beers and cocktails from well-known brands and distributors.
In Bridgeville, fall tastes like apples and scrapple—the love-it-or-hate-it meat that leaves no scrap unused. The old-time Apple Scrapple Festival even holds a Little Miss Apple Scrapple pageant. This year’s event will be Oct. 11–12.
Winter
The Quiet Resorts—including Bethany Beach and Fenwick Island—aren’t so silent in January. The Fire & Ice Festival includes a chili cookoff, music, a skating rink and ice carvings.
Related: Where to Find Delicious Italian Water Ice in Delaware
