Get ready for an action-packed first weekend of May in Coastal Delaware!
Whether you're looking for family fun, unique culinary experiences, or a chance to snag some great deals, this weekend promises a diverse array of exciting events across the area.
Spring Sidewalk Sale
Explore downtown Rehoboth Beach, Dewey Beach, and Route One for fantastic deals and unique finds. Participating businesses will be showcasing their offerings outdoors.
It's the perfect opportunity to shop local while enjoying fresh air and spring vibes!
- Date and Time: Friday, May 2nd through the 4th | Various times
- Locations: Downtown Rehoboth Beach, Dewey Beach, and Route One
Ocean to Bay Bike Tour
Kick off the beach season with a scenic bike ride. Join cyclists of all levels in the Quiet Resorts for a cycling tour through Sussex County’s beautiful beaches, bays, and more. Take part of the 10-mile Coastal Cruise up to Big Chill Beach Club and back to downtown Bethany.
- Date: May 2nd and 3rd
- Check all the information about schedule, registration, and location here.
Free Comic Book Day at Ogre's Grove
Celebrate comics with a free giveaway of various titles. This annual event offers a chance to discover new series and enjoy the world of comic books.
There will also be additional free comics for people in costumes.
- Date and Time: Saturday, May 3rd | 11 a.m. to 4 p.m.
- Location: 129 Union St., Milton
Southern Delaware Wine, Food, & Music Festival
Discover the culinary scene of Southern Delaware with wine tastings, delicious food vendors, and live musical performances.
This festival offers a vibrant taste of the region & this anticipated festival by many locals is going to be a showstopper this year.
- Date and Time: Saturday, May 3rd | 12 p.m. to 3:30 p.m.
- Location: Schellville, Rehoboth Beach
- Tickets available online.
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Water Family Fest and Native Plant Sale
Enjoy family-friendly activities focused on local water resources and the importance of native plants. You can also purchase native plants to enhance your own garden.
It’s a great way to connect with nature and learn more about sustainable landscaping.
- Date and Time: Saturday, May 3rd | 10 a.m. to 2 p.m.
- Location: 30048 Cedar Neck Rd., Ocean View
Kono Nation at Rusty Rudder
Get ready for a lively night of music as Kono Nation takes the stage. Expect a high-energy performance to kick off your Saturday night.
Go with your friends and dance the night away by the bay!
- Date and Time: Saturday, May 3rd | starts at 9 p.m.
- Location: 113 Dickinson Street, Dewey Beach
The Cork Jam
Experience an evening filled with live music from various cover bands. This event promises a diverse range of popular tunes to enjoy at Bottle & Cork.
The lively atmosphere makes it a favorite weekend stop for locals and visitors alike.
- Date and Time: Saturday, May 3rd | starts at 5 p.m.
- Location: 1807 Highway One, Dewey Beach
Milford Historical Society Spring Antique Show
Explore antiques, garden treasures, and local history at the Parson Thorne Mansion. This beloved spring event features antique vendors, a Milford Garden Club plant sale, light refreshments, and guided tours of the historic mansion led by costumed volunteers.
Date and Time: Saturday, May 3 | 9 a.m. to 3 p.m.
Location: Parson Thorne Mansion, Milford
Live Music with Kenny Riggs in Rehoboth
Enjoy an evening of great food and live music with Kenny Riggs. Head to Zogg’s Raw Bar & Grill for good vibes and amazing tunes by this talented local performer.
- Date and Time: Saturday, May 3 | 6 to 9 p.m.
- Location: Zogg’s Raw Bar & Grill, Rehoboth Beach
Lewes Farmers Market Opens for the Season
Celebrate the opening of the 20th season of the Historic Lewes Farmers Market with fresh local produce, meats, flowers, and more.
Hours and Locations:
Saturday Summer Market at George H.P. Smith Park
- May 3 – September 27, 2025
- 8am – 12pm
- Johnson & Dupont Aves
Wednesday Summer Market at Crooked Hammock Brewery
- June 4 – September 3, 2025
- 8am – 11:30am
- Crooked Hammock Way and Kings Highway
Saturday Fall Market at Lewes Elementary School
- October 4 – November 22, 2025
- 9am – 12pm
- 820 Savannah Rd
Saturday Holiday Market at Lewes Elementary School
- December 6, 2025
- 9am – 12pm
- 820 Savannah Rd
Author Book Signing at Browseabout Books
Meet author Thomas Guay and get a signed copy of his colonial-era novel, Chesapeake Bound: An Annapolis Novel. Discover a historical mystery filled with adventure, intrigue, and rich storytelling.
- Date and Time: Saturday, May 3 | 1 to 3 p.m.
- Location: 133 Rehoboth Ave., Rehoboth Beach
Mead, Merchants & Music at Brimming Horn
Celebrate the first Sunday of the month with craft vendors, live music, and mead at Brimming Horn Meadery. Shop local goods, enjoy food from La Pinkeria, and catch live sets including an open mic featuring local talent.
- Date and Time: Sunday, May 4 | 11 a.m. to 6 p.m.
- Location: 28615 Lewes Georgetown Hwy, Milton
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Jazz Brunch 5th Avenue Brunch
Indulge in a delightful brunch experience accompanied by the smooth sounds of live jazz music. The 5th Avenue Brunch provides a relaxing Sunday atmosphere.
Enjoy curated flavors, craft cocktails, and great company in a stylish setting.
- Date and Time: Sunday, May 4th | 11 a.m. to 1 p.m.
- Location: 32882 Cedar Grove Road, Lewes
- Ticket: $42
Cinco Days of Cinco
Big Chill Surf Cantina is celebrating 5 days and 5 nights of full on Cinco De Mayo festival fun.
Day 1: Hot Nights With Hot Sauce
Shake your maracas and hop in the conga line from 7-10 pm as local band Hot Sauce kicks off our Cinco De Mayo Celebration!
Enjoy $4 Modelos while the music is flowing!
Day 2: Margarita Contest
Join them from 4-6 pm for Cantina's first ever margarita contest featuring all the La Vida Hospitality brands including Big Chill Beach Club, Taco Reho, and Crooked Hammock Brewery.
Tasting tickets can be purchased the day of at the event so you can sample each marg and vote who you think should be crowned the winner.
Mama's Black Sheep will be performing from 6-9pm.
Day 3: The Big Fiesta!
The party starts at 2pm with an action packed day!
Festivities Include:
- Mechanical Bull | Available to ride for free from 2-6 PM
- DJ Magellan | 2-6 PM
- Live Music by: Mister VCR | 3-6 PM
- Mechanical Bull Contest | 5 PM
- $100 Cash prize
- Live Music by: Frazzlefit | 7-10 PM
- Taco Reho Food Truck | 1-10 PM
- Surfgimp Beneficiary | Donating 10% of sales
Day 4: Sunday Beach Daze Kickoff With LCB
What better way to celebrate Cinco eve than kicking off Sunday Beach Daze with Lower Case Blues from 4-7pm!
The outdoor bar will be open for service, and they'll be serving up some ice-cold drinks all night long.
Day 5: 5 de Mayo Marg Monday
No better way to close out this epic celebration than enjoying their $6 house margaritas all day long!
- Location: 19406 Coastal Hwy., Rehoboth Beach
Litzenberg to sign books at Historic Lewes
Meet local author Corinne Litzenberg and get a signed copy of her historical fiction book.
This is a great opportunity to learn about Lewes' past, and chat with the author about her inspirations!
- Date and Time: Friday, May 2nd | 4 p.m. to 7 p.m.
- Location: 110 Shipcarpenter Street, Lewes
4th Annual Kentucky Derby Day
Don your best hat and join the excitement of the Kentucky Derby. Enjoy watching the races, themed beverages, and perhaps even participate in some friendly competitions.
- Date and Time: Saturday, May 3rd | 4:30 p.m. to 7:30 p.m.
- Location: 17170 Harbeson Rd., Milton
- Ticket: $75
Shabbaton Weekend
Engage in a weekend of community, reflection, and learning through songs, stories, and teachings. Each gathering offers a welcoming space to connect, recharge, and celebrate tradition.
Check the schedule for locations and more details for individual events.
- Date and Time: From May 2nd to May 4th | Various times
- Location: Various locations
- Check each event to see if registration is needed!
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Long Meadow Ranch Wine Dinner
Savor a specially curated multi-course meal expertly paired with wines from Long Meadow Ranch.
This will be an elegant and flavorful dining experience. Wine lovers and foodies alike won’t want to miss it!
- Date and Time: Friday, May 2nd | 6 p.m. to 9 p.m.
- Location: 30115 Veterans Way, Rehoboth Beach
Brinner! - It's Breakfast, for Dinner
Experience a creative culinary event where breakfast dishes are reimagined for a dinner setting and paired with craft beers from Dogfish Head.
This promises a unique and tasty evening. Expect bold flavors, playful dishes, and a relaxed, foodie-friendly vibe.
- Date and Time: Friday, May 2nd | 6 p.m. to 8:30 p.m.
- Location: 320 Rehoboth Avenue, Rehoboth Beach
- Ticket: $75
With such a diverse range of activities happening throughout Coastal Delaware this weekend, you're sure to find something that sparks your interest.
Check back for more local event updates every week in our local area of Coastal Delaware by reading about them here on our blog!