This weekend in Seaford, DE

A flea market with vendor spaces available at $10 for each 10x10 area.

Celebrate the shift from late summer to early fall at the Wilderlove Outdoor Autumn Market, featuring handmade goods and vintage finds from Delaware and Maryland vendors. Browse and discover unique pieces at this seasonal outdoor shopping experience.

Delmar Heritage Day honors the community’s roots as a railroad town that straddles the Mason-Dixon Line, bringing neighbors together for artisan booths, food stands, and activities for all ages. A signature moment is the spirited tug-of-war that pulls from one side of the Maryland and Delaware border to the other. Grandpa Rich’s Jams, Jellies & Preserves returns to the festival. The celebration is presented by the Delmar Heritage Day Committee and takes place in downtown Delmar.

Backlash Fest 2026 brings a full day of live performances and community fun, presented by Bottle & Cork in Dewey Beach. The lineup features The British Invasion Years, A ’60s Musical Revolution, with special guests HeadHigh, Rogue Agents, and Clayton Eberly, and Mikey G as host. Attendees can enjoy music alongside local vendors, food, games, and a welcoming festival atmosphere in support of a good cause. Guests are encouraged to bring chairs and share the experience with friends. Event partners include J&A Electrical Services, Shore Water Refining, Long Neck Dispensary, Betterliving of Delmarva, George Hoffman Heating & Air Conditioning, AC Dreamscapes, J and C Home Exteriors, and Christina’s Cuts by the Coast. For those planning an overnight stay, Avid hotel Millsboro offers accommodations with a discounted room rate for Backlash 2026.

OktoBearFest returns to Seaford, featuring The TKO Band performing authentic polka music.

Enjoy live music by Josh Pryor. Food will be available from the Dominican King Lopez food truck.

This weekly Star Wars Unlimited tournament features a Constructed format with three Swiss rounds. Each round lasts 50 minutes and matches are played as best of three. Entry is $5.

DMTB, the Dave Matthews Tribute Band, brings a dinner and concert experience to the Wicomico Civic Center, honoring the songs that fans know and love. The set spans favorites from the 1990s and beyond, channeling the group’s signature groove with lively jams, moments made for singing along, and adventurous musicianship that reflects the spirit of the originals. Dinner is served before the show and features baked chicken with lemon and garlic, chef-carved roast baron of beef, sides such as roasted potatoes, corn pudding, a vegetable medley, and a garden salad with dressings, plus fresh rolls with butter. A chef-curated dessert table follows, along with iced tea, water, and freshly brewed coffee, and alcoholic beverages are available for purchase. The venue offers options for guests with special dietary needs, including preparations that avoid common allergens or ingredients tied to intolerances, and will make reasonable efforts to accommodate requests, though not all can be guaranteed. Guests may contact the venue manager in advance to discuss specific needs.

Take part in a Yu-Gi-Oh! trading card game tournament. The entry fee is $12, and every participant receives three OTS packs. If OTS supplies are limited, some of these will be replaced with other promotional packs.