Looking for something fun to do this weekend in Coastal Delaware? From food and art to nature walks and local history, there’s a little something for everyone this weekend here at the Coastal Delaware beaches!
Here is everything noteworthy happening this weekend across Coastal Delaware from May 16th to the 18th!
Dogfish Head PickleBrawl! Fest
Dogfish Head's PickleBrawl Fest at the Milton Brewery promises a high-energy blend of pickleball, exclusive brews, and flavorful bites for all of the local pickleball enthusiasts!
The brewery’s parking lot transforms into playful courts where beginners and seasoned players alike can enjoy a day of friendly competition.
Highlights include a limited-release PickleBrawl lager crafted with a medley of unique spices and vinegars, along with food vendors serving up pickle-themed treats. Vendors will include Uncle B’s Kitchen, Hula Bowls, Mommom's Cheesecakes, Drizzle's Pickles, GC Pickling Co., & MF Heat Co. with delicious options for everyone!
Visitors can browse pickleball gear from 302 Pickleball or catch an exhibition match featuring expert players at 1pm from First State Pickleball.
Make sure to bring your own paddles and gear if you plan to play, though they will have plenty available for sale! Additionally, if you would like to sit and watch, they highly encourage bringing a lawn chair to enjoy the games!
- Date: Saturday, May 17th
- Time: 11am to 6pm
- Location: 6 Cannery Village Center, Milton
- Cost: Book a pickleball court for $25 per hour & this comes with four drink tickets for the featured Picklebrawl beer
Lower Case Blues and Friends
Lower Case Blues, a very popular staple in this area as one of the favorite local bands this area has to offer, brings their high-energy blend of traditional blues and modern funk to The Listening Booth for an unforgettable live show. Known for their improvisational style and soulful grooves, this blues/jam trio has been captivating audiences since 2003.
Joining them for this show is special guest and friend of the band, Gabe Stillman, adding even more fire to an already dynamic lineup.
- Date: Friday, May 16th
- Time: 7pm to 9:30pm
- Location: 18388 Coastal Highway #11, Lewes
- Cost: $15 — $45
Launch Party for her New Book w/ Anne Colwell
Celebrate the launch of “Broken Heart Syndrome,” with local author Anne Colwell in an engaging event that blends literature, memory, and community. This collection of interconnected short stories explores life, loss, and emotional recovery with first hand experiences shared from a small beachside hospital in Lewes within this short story collection.
She will be joined in conversation by Maribeth Fischer of the Rehoboth Beach Writers Guild.
Attendees can participate online or in person and have the opportunity to purchase signed copies of the book.
- Date: Friday, May 16th
- Time: 5pm to 6:30pm
- Location: Lewes Public Library
- Cost: Event is free & open to the public
Lilith Fest
Lilith Fest brings the spirit of the Lilith Fair back to life with a powerful celebration of women in music. This tribute event features a lineup of performances that honor the groundbreaking artists who defined the original festival.
Held at the lively Bottle & Cork venue in Dewey Beach, the show promises an evening of nostalgia and empowerment. Fans of '90s alternative, folk, and rock will find plenty to love in this tribute to musical trailblazers.
- Date: Friday, May 16th
- Time: 8:30pm to 11:45pm
- Location: Bottle & Cork in Dewey Beach
- Cost: $24.75
Pour it On : A fluid acrylic class
“Pour It ON” is a hands-on fluid art class where you’ll dive into the world of acrylic pouring and create two unique paintings with the help of the brilliant teachers at Raye of Light Studio. Participants will explore the science behind fluid movement in paint, and choose from a vibrant color bar to design their own pieces.
The class covers two pouring methods (the dirty cup and the direct pour) each producing distinct effects in the resulting canvases.
All materials are provided, and your finished artwork will cure at the studio before pickup.
- Date: Friday, May 16th
- Time: 4pm to 6pm
- Location: 117 Atlantic Avenue, Ocean View
- Cost: $50.00
Don’t Tell Comedy
Get ready for a one-of-a-kind comedy experience at a secret location near you! This exclusive 21+ show promises a hilarious evening with a rotating lineup of 4-7 talented comedians, each kept a surprise until they hit the stage.
The best part? You’ll receive the exact location on the morning of the show, making it a true hidden gem. No drink minimums here, just good vibes and great laughs.
- Date: Saturday, May 17th
- Time: Doors open at 7pm; Show starts at 8pm
- Location: Secret locations; this date is somewhere in Rehoboth Beach
- Cost: $27
Villages of Five Points Plant and Bake
The Villages of Five Points Butterfly Club is hosting a charming plant and bake sale filled with nature-friendly finds and homemade treats. Shoppers can choose from a variety of flowering plants that attract butterflies, hummingbirds, and other pollinators, including milkweed, zinnias, and coneflowers.
Delicious baked goods like cookies, brownies, and small cakes will also be available, along with a selection of handmade items such as pet bandanas, garden-themed cozies, and Lewes-themed totes.
All proceeds support the club’s efforts to maintain butterfly-friendly habitats in the community.
- Date: Saturday, May 17th (severe weather date, May 18th)
- Time: 9am to 12pm
- Location: Old Orchard Road and West Edgemoor Road in the Villages of Five Points, Lewes
Lewes Maritime Day
The annual Lewes Maritime Day is a vibrant celebration of America’s rich maritime legacy, set along the scenic waterfront at Canalfront Park.
Guests can explore engaging exhibits and hands-on demonstrations that showcase the region’s deep-rooted nautical traditions. Enjoy live music, storytelling, and even a historical boat cruise to truly immerse yourself in the maritime spirit.
- Date: Saturday, May 17th
- Time: 11am to 3pm
- Location: 219 Pilottown Road, Lewes
- Cost: Event is free & open to the public ; $15 for add on ticket if interested for the Maritime Day History Cruise
Shanty Fest
Join Historic Lewes for their first annual Shanty Fest, a vibrant festival celebrating the maritime traditions of this historic town! The event will showcase small town Lewes and its deep connection to the sea through a dynamic mix of music, art, and history.
Highlights include everything from scrimshaw to tattoos, fascinating historical demonstrations, and artisanal crafts. Plus, enjoy live performances of sea-themed music, with the headliner being the renowned band, The Dreadnoughts.
- Date: Saturday, May 17th
- Time: 1pm to 7pm
- Location: 110 Shipcarpenter Street, Lewes
- Cost: $15
Rehoboth Arts Festival
The Rehoboth Art League returns to Grove Park with its annual outdoor arts festival, celebrating creativity in the heart of downtown.
This juried event showcases original works by RAL member artists, offering a unique opportunity to explore and purchase fine art in a relaxed, coastal setting.
The festival attracts art lovers from across the region, including visitors from major East Coast cities. In the event’s fifth year, they are looking forward to seeing everyone enjoy this beautiful day in Rehoboth Beach!
- Date: Saturday, May 17th, rain or shine!
- Time: 10am to 5pm
- Location: Grove Park, Rehoboth Beach
Don Fulano Tequila Dinner
Enjoy an unforgettable evening of flavor and festivity at the well loved SoDel restaurant, Papa Grandes, with a special cocktail dinner in the vibrant tequila room. Chef Emeley presents a thoughtfully crafted four-course menu designed to pair perfectly with selections from the Don Fulano tequila portfolio.
Each course highlights the bold and nuanced flavors of premium tequila, offering a unique culinary experience.
- Date: Saturday, May 17th
- Time: 6pm to 9pm
- Location: 38929 Madison Avenue, Selbyville
- Cost: $95 with gratuity included
St. Supery Estate Vineyards & Winery at Fish On
Fish On invites you to a memorable evening of fine dining and exceptional wine with winemaker Brooke Shenk from St. Supéry Estate Vineyards & Winery.
Guests will enjoy a curated selection of wines from this renowned Napa Valley estate, each introduced and explained by Brooke herself. Chef Ian has crafted a five-course menu that perfectly complements the wines, enhancing each flavor and pairing.
This is a unique opportunity to learn from a seasoned winemaker while savoring a gourmet culinary experience.
- Date: Friday, May 16th
- Time: 6pm to 9pm
- Location: 17300 North Village Main Boulevard, Lewes
- Cost: $114 with gratuity included
Sound Bath Meditation
Step into a peaceful oasis with the Self-Compassion Sound Bath at Dimitra Yoga.
This immersive experience blends guided meditation, intention-setting, and the healing vibrations of sound to support emotional release and deep relaxation. Participants are encouraged to bring a yoga mat, journal, and an open heart as they explore practices designed to promote inner peace and self-kindness.
Open to all levels, the session creates a welcoming space for reflection, clarity, and calm.
- Date: Sunday, May 18th
- Time: 2:00pm to 3:30pm
- Location: 17437 Ocean One Plaza (Suite 1), Lewes
- Cost: $40
Bethany Beach Books Welcomes Author Jeanine Cummins
Join bestselling author Jeanine Cummins for an intimate literary event, where guests will receive a copy of her latest novel “Speak to Me of Home,” along with entry to the event and a commemorative bookmark exclusive to attendees.
Jeanine will sit down for a conversation with Coastal Point editor, Darin McCann, offering insights into her writing and inspiration. Following the discussion, attendees will have the opportunity to meet the author and have their books signed to take home.
Grab a ticket to this one of a kind experience and meet a best selling New York Times author!
- Date: Sunday, May 18th
- Time: 1pm to 3pm
- Location: Dickens Parlour Theatre
- Cost: $35
Putt-Putt Tournament
Enjoy a day of mini-golf, food, and family fun at Jungle Jim’s while supporting a great cause. This spirited fundraiser helps provide memberships and programs for children and families through the Sussex Family YMCA.
With dedicated time slots for family and adult play, as well as lunch and drinks, there’s something for everyone to enjoy.
- Date: Sunday, May 18th
- Time: 12pm to 5pm
- Location: Jungle Jims in Rehoboth Beach
- Cost: $30 (Individual) $100 (Team)
Wheels for Meals
Enjoy beautiful rural Sussex County while riding in the 2025 Wheels for Meals event!
This fully supported ride to accommodate all….10 mile family ride, 25, 40, 50 & metric century, begins & ends at Hudson Field where you’ll enjoy a delicious barbeque chicken lunch, tasty beverages, great live music & incredible door prizes.
- Date: Saturday, May 17th
- Time: Various times
- Location: 29763 Eagle Crest Road, Milton
- Cost: $30 — $65
Spring Awakening
Clear Space Theatre brings a bold and electrifying production of Spring Awakening to the stage, capturing the raw intensity of youth, rebellion, and self-discovery.
Set in 19th-century Germany but pulsing with a modern rock score, this Tony Award-winning musical dives into the struggles of young people facing the weight of repression and desire.
With music by Grammy winner Duncan Sheik and lyrics by Steven Slater, the show challenges conventions and resonates deeply with contemporary audiences. Powerful, provocative, and emotionally charged, it redefines what a coming-of-age story can be.
- Date: May 16th — 18th
- Time: Friday & Saturday shows at 7pm, Sunday at 2pm
- Location: 20 Baltimore Avenue, Rehoboth Beach
- Cost: $21.50 — $38.50 per ticket
Bare: A Pop Opera
Experience the powerful and moving musical bare: A Pop Opera at the Milton Theatre, a show that explores love, identity, and the struggles of growing up in a world filled with societal expectations.
Set in a Catholic boarding school, this contemporary rock opera follows a group of students as they navigate their emotions, relationships, and the complexities of self-discovery. With its electrifying pop-rock score, stunning choreography, and heartfelt storytelling, bare promises to captivate and leave a lasting impact.
- Date: May 16th — 18th
- Time: Friday’s show at 7:30pm, Saturday’s shows at 2pm and 7:30pm, and Sunday’s show at 2pm
- Location: 110 Union Street, Milton
- Cost: $32.65 — $51.19
The Starboard
Join the fun at The Starboard for an exciting weekend of live music and great vibes! On Friday, enjoy the energetic sounds of Decade 80, bringing back the best hits of the '80s.
Saturday features the lively 19th Street Band, setting the perfect mood for an unforgettable night.
Wrap up the weekend on Sunday with Kristen & the Noise Acoustic, offering a relaxed, acoustic performance.
- Date: May 16th — 18th
- Time: Various
- Location: 2009 Coastal Highway, Dewey Beach
Summer Market at George H.P. Smith Park
The Historic Lewes Farmers Market (HLFM), which is a nonprofit organization committed to nurturing a vibrant local food system in Delmarva that is sustainable and socially responsible, is a hit for every farmer’s market lover.
It offers everything from fresh baked goods to home decor to fresh produce and homemade goodies.
- Date: Every Saturday from May 3rd to September 27th
- Time: 8am to 12pm
- Location: Johnson & Dupont Aves, Lewes
Steel Magnolias
We highly recommend making time to enjoy a new live play at the Second Street Players's Riverfront Theater in Milford!
The action is set in Truvy’s beauty salon in Chinquapin, Louisiana, where all the ladies who are “anybody” come to have their hair done. Helped by her eager new assistant, Annelle, the outspoken, wise-cracking Truvy dispenses shampoos and free advice to the town’s rich curmudgeon, Ouiser; an eccentric millionaire, Miss Clairee, who has a raging sweet tooth; and the local social leader, M’Lynn.
Filled with many laughs and seeing special qualities in these characters across the stage to make this production truly touching, this is being labelled as a must-see show!
- Dates & Times: May 16th at 7pm, May 17th at 7pm, and May 18th at 2pm
- Location: 2 South Walnut Street, Milford
- Cost: $27
Sussex County Habitat for Humanity Annual Golf Outing
Support a great cause at the 2025 Annual Golf Outing, hosted by Sussex County Habitat for Humanity!
Though participant tickets are sold out, you can still make an impact by becoming a sponsor for this exciting event if interested.
Sponsorships offer fantastic visibility for your business while supporting the mission to build affordable homes in Sussex County.
- Date: Friday, May 16th
- Location: Midway Par 3, Lewes
Make the most of your weekend by exploring all that Coastal Delaware has to offer. Check out weekly event highlights and be sure to follow our blog to stay in the loop on everything happening around the area!