Labor Day weekend is the perfect time to soak up those final summer days in Coastal Delaware.
The beaches are alive with music, markets, and community gatherings, while local bookstores and theaters add culture and fun to the mix.
Whether you’re spending your time in Lewes, Rehoboth, Bethany, or Fenwick Island, there’s something happening that will make your weekend unforgettable.
West Side Creative Market
Creativity shines at the West Side Creative Market, where local artists and makers come together to share their work.
This Labor Day weekend, the market is open Friday, August 29th, with Julie Derrick performing live, and again on Monday, September 1st, with Bryan Scar bringing the music.
It’s a laid-back evening event where you can browse art, enjoy music, and connect with the local creative scene.
- Dates: August 29th and September 1st
- Time: 5pm – 9pm
- Location: 19826 Central Street, Rehoboth Beach
Fenwick Island Farmers Market
While the Fenwick Island Farmers Market officially runs through the end of August, it sets the tone for the long weekend with its celebration of local agriculture.
Held on Fridays at The Station, the market is a true gathering place for the community.
Even as the season winds down, it captures the spirit of summer with homegrown flavors and friendly faces.
- Date: August, 29th
- Time: 8am – 12pm
- Location: 1406 Coastal Highway, Fenwick Island
Saturday Summer Market at George H.P. Smith Park
Start your Saturday morning with a stroll through the market at George H.P. Smith Park in Lewes.
From 8 a.m. to noon, the park fills with fresh produce, flowers, and locally made goods that highlight the best of Delaware’s coastal community.
It’s the kind of place where you can sip coffee, chat with neighbors, and stock up on everything you need for a weekend feast.
- Date: August 30th
- Time: 8am – 12pm
- Location: Johnson & Dupont Aves, Lewes
Bethany Beach Farmers’ Market
On Sunday morning, the Bethany Beach Farmers’ Market brings together local farmers and makers for a market filled with coastal charm.
Open from 8 a.m. to noon, it’s a relaxed and friendly stop before heading to the beach.
Fresh fruits, baked goods, and artisan items make it easy to pick up a few last tastes of summer.
- Date: August, 31st
- Time: 8am – 12pm
- Location: Garfield Parkway & Pennsylvania Avenue, Bethany Beach
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Nassau Valley Vineyards Farmers’ Market
Tucked among the vines in Lewes, Nassau Valley Vineyards hosts its Sunday farmers’ market from 12 to 3 p.m. all summer long through mid-October.
With over 20 vendors, the market is a treasure trove of local produce, baked goods, artisanal products, and, of course, wine.
It’s the kind of Sunday outing where you can sip, stroll, and shop, making it an ideal way to wrap up the weekend.
- Date: August, 31st
- Time: 12pm – 3pm
- Location: 32165 Winery Way, Lewes
Browseabout Books Events
Browseabout Books has a full lineup of events for Labor Day weekend.
On Saturday, August 30th, authors Will Freshwater and BJ Irons will be signing Rest Ashored from 11 a.m. to 1 p.m., followed by Darcy Coates signing How Bad Things Can Get from 1:30 to 3:30 p.m.
Then on Sunday, August 31st, comedian and author Zach Zimmerman will host a talk and signing at CAMP Rehoboth. It’s the perfect stop for book lovers who want to meet authors and discover new reads.
- Dates: August 30th and 31st
- Browseabout Books Location: 133 Rehoboth Avenue, Rehoboth Beach
- CAMP Rehoboth Atrium Location: 37 Baltimore Avenue, Rehoboth Beach
Bethany Beach Books Events
Bethany Beach Books is also celebrating the holiday weekend with something for readers of all ages.
On Saturday, August 30th, bestselling author Madeline Martin will be in store at 6:30 p.m. to meet fans and sign her newest book, The Secret Book Society.
Then, on Monday morning, the shop hosts its beloved Story Time, where kids can enjoy a lively reading and families receive a $5 coupon to use toward books.
It’s a great way to close out the weekend with a cozy community event.
- Dates: August 30th and 31st
- Location: 133 Rehoboth Avenue, Rehoboth Beach
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Freeman Arts Pavillion Events
Live entertainment takes center stage at the Freeman Arts Pavilion all weekend long.
On Friday night, August 29th, families can enjoy the incredible illusions of Bill Blagg at 7 p.m.
Saturday brings the high-energy tribute band Changes in Latitudes with all the Jimmy Buffett classics, while Sunday caps things off with a performance from Grammy-winning artist Maren Morris.
It’s an unbeatable lineup for music fans looking to make their holiday weekend unforgettable.
- Dates: August 29th — 31st
- Location: 31806 Lakeview Drive, Selbyville
Milton Theater Events
The historic Milton Theatre has a diverse schedule lined up for Labor Day weekend.
Friday, August 29th, audiences can step back in time with Rat Pack Together Again, offered at both 2 and 7 p.m.
Saturday afternoon brings the soulful sounds of Magic of Motown, while Sunday closes the weekend with an intimate evening featuring psychic medium Deanna Fitzpatrick.
It’s a mix of nostalgia, music, and mystique, all in the heart of Milton.
- Dates: August 29th — 31st
- Location: 110 Union Street, Milton
The Listening Booth
For a more intimate music experience, The Listening Booth in Rehoboth Beach is the perfect stop this Labor Day weekend.
On Friday night, Goldpine takes the stage with Cathy Jane from 7 to 9:30 p.m., filling the room with rich, soulful sounds.
Saturday keeps the momentum with Pierce Pettis and Eli Lev, blending folk and storytelling in a cozy setting.
On Sunday, the vibe shifts to a lively Social Jam Night, running from 8 p.m. until midnight, where local talent and music lovers come together to close out the weekend in true community style.
- Dates: August 29th — 31sh
- Location: 18388 Coastal Highway, Lewes
Paradise Grill Events
Paradise Grill is always a lively place on the bay, and Labor Day weekend promises non-stop entertainment.
From Friday through Monday, the stage will feature a wide range of performers including Kristen and the Noise, The Fabulous Greaseband, Gypsy Wisdom, and The Funsters.
With multiple shows each day, it’s easy to stop by for a drink, catch live music by the water, and soak up the summer atmosphere.
- Dates: August 29th — September 1st
- Location: 110 Union Street, Milton
- Check out all their events here
Big Chill Beach Club Events
The Big Chill Beach Club is the perfect spot to take in the sunset with live music.
On Friday night, Nick Kashmanian takes the stage, followed by Frazzlefit on Saturday, and Joe Esham on Sunday.
With a drink in hand and ocean views stretching out before you, it’s hard to imagine a better way to celebrate the season’s end.
- Dates: August 29th — 31st
- Time: 6 — 9pm
- Location: 27099 Coastal Highway, Bethany Beach
- Check out all their events here
Bottle & Cork Events
Known as the “Greatest Rock and Roll Bar in the World,” Bottle & Cork will be buzzing with energy all weekend.
Their signature Jam Sessions kick off each night at 5 p.m., featuring a mix of local favorites and well-known acts.
From The Gab Cinque Band and Love Seed Mama Jump to Triple Rail Turn and DJ Knappy, the shows keep the party going late into the night.
- Dates: August 29th — 31st
- Location: 18047 Highway One, Dewey Beach
- Check out all their events here
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The Starboard
The Starboard is one of Dewey Beach’s most legendary spots, and Labor Day weekend brings plenty of live music to keep the energy high.
On Friday night, the party kicks off with Just the Tip at 10 p.m., followed by Johnny Phatt taking the stage on Saturday afternoon.
Sunday doubles the fun with The 19th Street Band in the afternoon and Kristen Acoustic rounding out the night.
With its lively atmosphere and packed schedule, The Starboard is the place to be for holiday weekend fun.
- Dates: August 29th — 31st
- Location: 2009 Coastal Highway, Dewey Beach
- Check out all their events here
Rusty Rudder Events
Another Dewey Beach classic, the Rusty Rudder has a full lineup of live music over the holiday weekend.
Acts include Stealing Savanah, The Gab Cinque Band, Carley Twigg Duo, and Love Seed Mama Jump.
With its unbeatable bayside views and back-to-back performances, the Rudder is a must-visit spot for anyone looking to enjoy music and summer vibes.
- Dates: August 29th — 31st
- Location: Dickinson Avenue and the Bay, Dewey Beach
- Check out all their events here
Bethany Beach Bandstand
The Bethany Beach Bandstand tradition continues with free concerts every night of the holiday weekend.
On Friday, Love Seed Mama Jump will get the crowd dancing, followed by Still Surfin’ on Saturday and Jesse Garron on Sunday.
With music starting at 7:30 p.m., it’s the perfect way to end a beach day with family and friends.
- Dates: August 29th — 31sh
- Location: Boardwalk, Bethany Beach
Rehoboth Beach Bandstand
Rehoboth’s iconic Bandstand also has a festive lineup. Still Surfin’ kicks off the weekend on Friday night, and on Saturday, Parrotbeach brings Jimmy Buffett’s tropical sound to the stage.
Concerts begin at 8 p.m. and offer a classic boardwalk experience that’s full of energy and community spirit.
- Dates: August 29th and 30th
- Location: Rehoboth Ave, Rehoboth Beach
Labor Day weekend is always a special time in Coastal Delaware, filled with music, food, and gatherings that capture the heart of summer.
Which of these events are you most excited about? Share your plans in the comments below, and if you’re thinking about making Coastal Delaware your permanent getaway, our team is here to help you find the perfect home by the beach.