Looking for the best ways to enjoy the first weekend of May around Delmarva? From coastal festivals to live music and art shows, there’s something for everyone. Here’s your B106-approved roundup of can’t-miss events happening this weekend.
????? Rehoboth Spring Sidewalk Sale (May 2–4)
Downtown Rehoboth Beach, Dewey Beach & Route 1
Score major deals during the 42nd Annual Spring Sidewalk Sale. Local shops bring their best bargains outdoors for a weekend of shopping fun. Early birds get the best picks, but Sunday often brings the deepest discounts.
???? Southern Delaware Wine, Food & Music Festival (May 3)
Schellville Village, Lewes
Indulge in unlimited tastings from top chefs, wineries, and breweries at this beloved annual event. Enjoy live music, bourbon tastings, and immersive experiences—all while supporting local nonprofits.
???? Berlin Jazz, Blues, Wine & Brews (May 3)
Downtown Berlin, MD
This fan-favorite festival returns with local beer, wine, mead, and spirits. Stroll through art displays, enjoy live music, and savor the best eats Berlin has to offer. Free to attend with free parking.
???? Hadestown at The Playhouse (May 2–4)
Rodney Square, Wilmington
Experience the Tony Award-winning musical "Hadestown" during its limited run in Wilmington. A must-see for theater enthusiasts.
???? Art Exhibitions & Workshops
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Delaware Watercolor Society: The Best of DWS 2025
Rehoboth Art League (Through May 4)
Explore stunning watercolor pieces from talented artists. -
Resin Waves Serving Board Workshop
Milton Arts Guild (May 2)
Create your own resin art serving board in this hands-on workshop.
???? Live Music & Performances
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Micky Dolenz of The Monkees: Songs & Stories
The Grand Opera House, Wilmington (May 2)
Enjoy an evening of music and memories with Micky Dolenz. -
Melody Trucks & The Fitzkee Brothers LIVE
The Listening Booth (May 4)
Catch this dynamic performance blending soulful melodies and energetic rhythms.
???? Water Family Fest & Native Plant Sale (May 3)
Lewes, DE
Join the Water Family Fest for a day of environmental education, family activities, and a native plant sale to support local ecosystems.
????? Art Exhibitions to Explore
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Doors of Fame
Rehoboth Art League (Through October 31)
Discover artistic interpretations of iconic doors and their stories. -
In Line | Out of Line
Agora Gallery (Through May 23)
An exhibition exploring the boundaries of artistic expression.
????? The Market at the Center for the Creative Arts (May 4)
Hockessin, DE
Browse handmade goods, art, and crafts from local vendors at this vibrant market.
