Events
May Events at the Delaware Beaches
Sussex County Beach Living | May 2026
Farmers Markets
- May 2, 9, 16, 23, 30 — Historic Lewes Farmers Market — George H.P. Smith Park, Lewes — 8am–12pm — Learn More
- May 5, 12, 19, 26 — Rehoboth Beach Farmers Market — Grove Park, Rehoboth Beach — 10am–2pm — Learn More
- May 8, 15, 22, 29 — Milton Farmers & Artisan Market — Grace Church, 514 Union St., Milton — 3:30–6pm — Learn More
- May 31 — Bethany Beach Farmers' Market Opening Day — PNC Bank Parking Lot, Garfield & Pennsylvania Ave. — 8am–12pm — Learn More
Art Shows & Creative Events
- May 2–24 — "Shadow and Light" Exhibition — Peninsula Gallery, Lewes — Learn More
- May 8–June 28 — Rehoboth Art League Exhibitions — Rehoboth Art League, Rehoboth Beach — Learn More
- May 9 — Dewey Beach Arts & Fun Festival — Dickinson Street & Bay, Dewey Beach — 9am–3:30pm — Learn More
- May 16 — Rehoboth Beach Arts Festival — Grove Park, Rehoboth Beach — 10am–5pm — Learn More
- May 30–June 21 — "Abstract Construction" Exhibition — Peninsula Gallery, Lewes — Learn More
Free Outdoor Music & Beach Concerts
- May 23 — Soul Crackers — Rehoboth Beach Bandstand — 8pm — Learn More
- May 24 — Parrotbeach — Rehoboth Beach Bandstand — 8pm — Learn More
- May 28 — Matt Lafferty & The Pros from Dover — Lewes Canalfront Park — 6:30–8:30pm — Learn More
- May 31 — Bethany Beach Seaside Craft Show Begins Sundays — Bethany Beach Boardwalk/Bandstand Area — Learn More
Live Music at Restaurants & Venues
- May 1 — The Benderz, DJ Zip & DJ Scooter — Northbeach, Dewey Beach — Learn More
- May 8 — The Legwarmers — Bottle & Cork, Dewey Beach — 8:30pm — Learn More
- May 8 — Salty Soles — Dockside Marina Bar & Grill, Lewes — 5–8pm — Learn More
- May 9 — Angelee — Dockside Marina Bar & Grill, Lewes — 5–8pm — Learn More
- May 15 — Tommy Conwell & The Young Rumblers — Bottle & Cork, Dewey Beach — 8pm — Learn More
- May 16 — Backlash — Irish Eyes, Lewes — 8:30pm–12am — Learn More
- May 21 — moe. — Bottle & Cork, Dewey Beach — 8pm — Learn More
- May 22 — Julia Her, DJ Zip & DJ Scooter — Northbeach, Dewey Beach — 5–11pm — Learn More
- May 29 — Split Decision — Bottle & Cork, Dewey Beach — 8pm — Learn More
State Park & Outdoor Activities
- May 2 — Cape 75 Nature Challenge: Tracks and Trails — Cape Henlopen State Park — 10–11am — Learn More
- May 16 — Cape Nature 250 to Today Hike — Cape Henlopen State Park — 10–11am — Learn More
- May 30 — History Hike: The Seaside — Delaware Seashore/Fenwick Island Area — 1–2pm — Learn More
- May 31 — Night Hike: Once in a Blue Moon — Delaware State Parks Program — 8:30–10pm — Learn More
Family Fun, Festivals & Summer Openings
- May 1 — Historic Lewes First Friday Community Night — Historic Lewes Campus, 110 Shipcarpenter St. — 4–7pm — Learn More
- May 2 — British Motorcar Show — Cape May-Lewes Ferry Terminal — 11am–3pm — Learn More
- May 9 — Funland Opening Day — Rehoboth Beach Boardwalk — Learn More
- May 9 — Dogfish Head Dock Dogs — Milton/Lewes Area — Learn More
- May 9 — Historic Lewes 2nd Annual Shanty Fest — Historic Lewes Campus — 1–7pm — Learn More
- May 16 — Funland Haunted Mansion Opens — Rehoboth Beach Boardwalk — Learn More
- May 16 — Overfalls Museum Grand Opening / Maritime Day — Lewes Canalfront Park — 11am–3pm — Learn More
- May 21 & 23 — Walk to DeBraak — Zwaanendael Museum / Historic Lewes — Learn More
- May 22–25 — Bethany Beach Poseidon Festival — Bethany Beach — Learn More
- May 23–25 — Jungle Jim's Waterpark Opening Weekend — Rehoboth Beach — 10am–5pm — Learn More
- May 25 — Lewes Memorial Day Parade — Lewes — 11am — Learn More
- May 30 — Lewes in Bloom Plant Sale — 218 Schley Ave., Lewes — 9am–1pm — Learn More
Movies & Film
- May 9 — No Fun Films Roadshow with Filmmaker Q&A — Cinema Art Theater, Lewes — Learn More
- May 14–16 — Rehoboth Beach PRIDE Film Fest — Cinema Art Theater, Lewes — Learn More
- May 30 — The Met: Live in HD, El Último Sueño de Frida y Diego — Cinema Art Theater, Lewes — Learn More
Note: Many outdoor movie series and beach-town summer concert series begin in June, including Dewey Beach Monday Movies, Dewey Beach Summer Concert Series, Lewes Stango Park Concert Series, and Bethany Beach Seaside Concert Series.
Free Outdoor Music & Beach Concerts
- May 20 — Sounds of Summer Concert in the Park — Milton Memorial Park, Milton — 7pm — Learn More
- May 21 — Quayside @ Nite with Lower Case Blues — Milton Theatre Quayside, Milton — 6pm — Learn More
- May 28 — Quayside @ Nite with Girls Room — Milton Theatre Quayside, Milton — 6pm — Learn More
Live Music at Restaurants, Breweries & Wineries
- May 1 — Dogfish Head Events & Specials — Milton Brewery and Rehoboth locations — Learn More
- May 1 — R&R Line Dancing — Salted Vines Vineyard & Winery, Frankford — 5:30pm — Learn More
- May 2 — Rick Arzt — Salted Vines Vineyard & Winery, Frankford — 1pm — Learn More
- May 8 — Steve Bowers — Big Oyster Brewery, Lewes — 5–8pm — Learn More
- May 8 — Nate McCormick — The Wheelhouse, Lewes — 6–9pm — Learn More
- May 9 — Tim Jaudon — Big Oyster Brewery, Lewes — 5–8pm — Learn More
- May 9 — Troll Tribe — Big Chill Surf Cantina, Rehoboth Beach — 8–11pm — Learn More
- May 10 — Bryan Scar — Big Oyster Brewery, Lewes — 5–8pm — Learn More
- May 24 — Love Seed Mama Jump — Salted Vines Vineyard & Winery, Frankford — 6–9pm — Learn More
- May 29 — Troll Tribe — Big Chill Surf Cantina, Rehoboth Beach — 8pm — Learn More
- May 2026 — Rehoboth Ale House Live Music Calendar — Rehoboth Beach — Learn More
- May 2026 — Harpoon Hanna's Entertainment Calendar — Fenwick Island — Learn More
Theatre Shows
- May 1–23 — Dear Evan Hansen — Clear Space Theatre, Rehoboth Beach — Learn More
- May 2–17 — Nunsense II: The Second Coming — Milton Theatre, Milton — Learn More
- May 4–21 — The Legend of Georgia McBride — Clear Space Theatre, Rehoboth Beach — Learn More
- May 6 — Carole King Meets the Beatles — Milton Theatre, Milton — 7:30pm — Learn More
- May 10 — Dueling Pianos with Flying Ivories — Milton Theatre, Milton — 7pm — Learn More
- May 13 — Simply Streisand — Milton Theatre, Milton — 7:30pm — Learn More
- May 17 — Psychic Medium Deanna Fitzpatrick — Milton Theatre, Milton — 3pm — Learn More
- May 24 — Angry Young Band: Billy Joel Tribute — Milton Theatre, Milton — 7:30pm — Learn More
- May 27 & 29 — Movie Musicals: Musical Theatre Ensemble Spring Showcase — Milton Theatre, Milton — Learn More
Boat Tours & Cape Water Taxi
- May 2026 — Cape Water Tours & Taxi Season Begins — Lewes docks at Anglers Road and Cape Henlopen Drive — Learn More
- May 16 — Maritime Day History Cruise — Cape Water Tours, Lewes-Rehoboth Canal — Learn More
- May 2026 — Water Taxi to Rehoboth, Sunset Cruises, Lighthouse Cruises & Canal Cruises — Cape Water Tours, Lewes — Learn More
