Coolest Upcoming Coastal Delaware Events: Handpicked by Our Team Pt. 3

There is no slowing down when it comes to events in Coastal Delaware, and this next round proves it. 

From creative workshops and live music to community festivals, comedy shows, and day trips, there are so many ways to get out and enjoy the area. 

This list has a lot of fun things to do in Coastal Delaware, whether you're planning your weekends ahead of time or just looking for something new to do:

Raye of Light Studio: Watercolor on Yupo

Raye of Light Studio’s Watercolor on Yupo class is a great opportunity for anyone who has struggled with traditional watercolor or is simply curious to try something new. 

Using Yupo, a synthetic paper that doesn’t absorb paint, this class gives beginners more time to work, adjust, and experiment without the pressure of quick drying. 

You will learn the fundamentals of color mixing and lifting techniques in a more forgiving and freeing way, creating a completely different watercolor experience. 

All materials and instruction are provided, making it an easy and approachable way to explore a new creative process from start to finish.

  • Date: March 31, 2026
  • Hours: From 6pm to 8:30pm
  • Address: 117 Atlantic Avenue #3F, Ocean View
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Rehoboth Art League’s Bus Trip: Baltimore Museum of Art

The Rehoboth Art League’s bus trip to the Baltimore Museum of Art offers a full day of art, culture, and exploration centered around the special exhibition “Amy Sherald: American Sublime.” 

The exhibition features 38 paintings spanning from 2007 to the present, highlighting Sherald’s evolution as an artist and including her well-known portrait of former First Lady Michelle Obama. 

In addition to the featured exhibit, visitors can explore an impressive range of collections throughout the museum, from modern masterpieces in the Cone Collection to works from Native North America, African art from more than 200 states and societies, and European pieces from the 15th through 19th centuries. 

Guests will also have time to explore the Sculpture Gardens if weather allows and enjoy lunch on their own at nearby dining options or Gertrude’s Chesapeake Kitchen.

  • Date: April 1, 2026
  • Hours: Bus leaves at 8am for the trip!

2026 Lewes Tulip Celebration

The Lewes Tulip Celebration is a beloved annual tradition that brings a burst of color and a nod to the town’s Dutch heritage, with more than 31,000 tulips and 5,000 spring bulbs planted throughout Lewes. 

Spread across multiple weekends, the celebration invites visitors to explore over 20 locations using the Tiptoe To The Tulips Map, available at the Lewes Chamber of Commerce’s Visitor Center in the historic Fisher Martin House at Zwaanendael Park and at brochure boxes around the historic district. 

In addition to strolling through vibrant displays, visitors can enjoy special events like the tulip sale at Bank Street Plaza and guided “History in Bloom” walking tours that combine Lewes’ maritime history with insights into the many tulip varieties planted throughout town.

  • Dates: April 1-19, 2026

The Listening Booth: Claudia Hoyser

The Listening Booth welcomes Claudia Hoyser for an intimate live music experience featuring one of today’s rising voices in Americana and indie country. 

Known for her smoky tone and distinctive style, Hoyser has built a strong independent following with over 120 million organic views, charting singles, and appearances in national campaigns and international films. 

Having shared the stage with artists like Keith Urban, Miranda Lambert, and Little Big Town, she brings both talent and experience to this performance, along with music from her recently released sophomore album “Before The Dawn,” making it a must for fans of modern country and singer-songwriter sounds.

  • Date: April 3, 2026
  • Hours: From 7pm to 9:30pm
  • Address: 18388 Coastal Hwy #11, Lewes

Mama's Black Sheep Live at Crooked Hammock

Mama’s Black Sheep live at Crooked Hammock offers a laid-back night of music paired with the easygoing atmosphere the brewery is known for. 

With craft beer brewed on site, the smell of freshly grilled food in the air, and outdoor games like cornhole and ping pong, it is the kind of place where you can settle in and stay awhile. 

Add in live music from Mama’s Black Sheep and you have a relaxed, social setting that is perfect for gathering with friends, enjoying good food and drinks, and making the most of a casual night out.

  • Date: April 11, 2026
  • Hours: From 5pm to 8pm
  • Address: 36707 Crooked Hammock Way, Lewes

Don’t Tell Comedy 

Don’t Tell Comedy offers a completely different kind of night out, built around surprise, spontaneity, and seriously good stand-up. 

With secret locations revealed the morning of the show and a lineup of comedians that stays under wraps until they hit the stage, every event feels like a one-of-a-kind experience.

Each show features a curated mix of four to seven performers, blending local talent with nationally touring comedians, so you might discover your new favorite comic or catch someone you already love. 

  • Date: April 11, 2026
  • Hours: Doors open at 6pm
  • Location: Lewes

It’s A Bloomin’ Dance Party 2026—A Benefit Event for Rehoboth In Bloom

It’s a Bloomin’ Dance Party brings the community together for a lively night of music, dancing, and giving back. 

With live tunes from The Funsters setting the tone, the dance floor is sure to stay full as guests celebrate while supporting Rehoboth in Bloom’s ongoing beautification efforts. 

Every ticket purchased helps fund projects that keep the town looking its best year round, from public spaces to local business areas, making this an event where you can have fun and make a meaningful impact at the same time.

  • Date: April 17, 2026
  • Hours: From 7pm to 10pm
  • Address: 229 Rehoboth Avenue, Rehoboth Beach

Wilmington Ballet at the Milton Theatre

Wilmington Ballet takes the stage at the Milton Theatre with AXIS, a powerful and contemporary performance that blends ballet and modern dance into an emotional exploration of self-discovery and connection. 

Featuring original works by choreographers Kamani Abu, Miguel Quinones, Rachelle Rafailedes, and Benjamin Sterling Cannon, along with a live vocal element from Fred Reed, the production moves beyond traditional storytelling to create a deeply personal and reflective experience. 

Through striking choreography and expressive movement, AXIS invites the audience to consider the balance between self, love, and life’s direction in a visually compelling and thought-provoking way.

  • Date: April 19, 2026
  • Hours: Doors open at 6pm
  • Address: 110 Union Street, Milton
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Doodles in Dewey to Benefit PAWS for People

Doodles in Dewey to benefit PAWS for People is a joyful, multi-day celebration that brings together doodle dogs of all kinds and their humans for a weekend full of community, fun, and giving back. 

From the lively costume parade along the Rehoboth Boardwalk to beachside gatherings, yoga sessions, and a series of “yappy hours” at local spots, the event offers something for everyone while supporting a nonprofit dedicated to providing meaningful pet therapy services. 

With hundreds of participants and pups joining each year, it is a heartwarming and energetic experience that welcomes both returning attendees and new friends to be part of a growing tradition.

  • Dates: April 24-26, 2026
  • Hours: Various
  • Location: Various 

Rehoboth Art League’s Bus Trip: Hillwood Estate, Museum & Gardens

The Rehoboth Art League’s bus trip to Hillwood Estate, Museum & Gardens offers a full day immersed in art, history, and beautifully designed landscapes at one of Washington, D.C.’s most elegant house museums. 

Founded by Marjorie Merriweather Post, Hillwood showcases an extraordinary collection that includes Russian imperial art and refined French decorative pieces, all displayed throughout a stunning mansion that reflects her passion for collecting. 

Beyond the interiors, guests can explore thirteen acres of formal gardens, from a French parterre and rose garden to a Japanese-style garden and greenhouse spaces.

The experience also includes a docent-led tour of the estate and museum collections, along with time to explore at your own pace and enjoy lunch at the onsite Merriweather Café.

  • Date: May 5, 2026
  • Hours: Bus leaves at 8am
  • Address: 511 Rehoboth Avenue, Rehoboth Beach
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Want to stay in the loop on everything happening around Coastal Delaware? Keep following our blog for more event roundups, local guides, and insider tips on what to do across the area!

Have any questions about our blog(s), the Coastal Delaware real estate market, or local life in our beautiful beach towns? Do you think there is something we should write about? Did you see an event coming up that we should know about? Shoot us an email at [email protected] or give us a call at (302) 212-0074. We would love to hear from you!

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