From theater productions and well-known musicals to live concert performances, Coastal Delaware has a variety of shows coming up for anyone looking to plan a fun outing in the weeks ahead. 

With performances scheduled in places like Rehoboth Beach, Georgetown, Milton, Lewes, and Selbyville, this roundup is a good place to start if you want to see what is coming up around the area.

The Legend of Georgia McBride at Clear Space Theatre

The Legend of Georgia McBride brings a bold, funny, and surprisingly heartfelt story to the stage at Clear Space Theatre. 

Written by Tony Award winner Matthew Lopez, the show follows an Elvis impersonator working at a run-down Florida bar who suddenly finds himself out of options just as life is about to get more complicated, with a baby on the way. 

What starts as a desperate situation quickly turns into something completely unexpected when he steps into the world of drag, trading his blue suede shoes for wigs, heels, and a whole new persona. 

With sequins, stilettos, and a lot of humor along the way, the story explores identity, self-discovery, and what it really means to find your voice. 

It is a comedy at its core, but one that leans into deeper themes about acceptance, chosen family, and breaking past expectations, all while delivering a fun and energetic performance that keeps the audience engaged from start to finish.

• Dates: May 4th-20th
• Address: 20 Baltimore Avenue, Rehoboth Beach

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Dear Evan Hansen at Clear Space Theatre

Dear Evan Hansen is one of those productions that resonates on a much deeper level, and seeing it live at Clear Space Theatre brings that experience even closer to home. 

This Tony Award-winning musical, with a book by Steven Levenson and music and lyrics by Benj Pasek and Justin Paul, tells the story of Evan, a high schooler struggling with anxiety and a strong desire to feel seen and understood. 

When a single lie spirals into something much bigger, Evan finds himself navigating a complicated situation that forces him to question who he is and who he wants to be. 

The show captures both the emotional highs and lows that come with connection, loneliness, and the pressure to belong, all set against a powerful and recognizable soundtrack. 

It is a story that has connected with audiences across generations, offering moments that feel personal, honest, and, at times, difficult in the best way, while also reminding viewers that even in the darkest moments, no one is truly alone.

• Dates: May 1st-23rd
• Address: 20 Baltimore Avenue, Rehoboth Beach

Mary Poppins at Possum Point Players

Mary Poppins at Possum Point Players brings a familiar and beloved story to the stage, combining the magic of the original tales by P.L. Travers with the charm of the classic Disney film. 

Set in London in 1910, the production follows the Banks family and their two children, Jane and Michael, who have already driven away several nannies before Mary Poppins arrives at their doorstep. 

With her unique mix of magic and practicality, she sets out to restore balance in the household and help the family reconnect in ways they did not expect. 

Along the way, the show introduces memorable characters like Bert, a jack-of-all-trades who guides the audience through the story, and features well-known songs such as “A Spoonful of Sugar,” “Let’s Go Fly a Kite,” and “Chim Chim Cher-ee.” 

With its mix of music, storytelling, and visual charm, this production captures the sense of wonder that has made Mary Poppins a favorite for generations, while still carrying a message that resonates just as much with adults as it does with kids.

• Dates: May 29th-June 7th
• Address: 441 Old Laurel Road, Georgetown

Rehoboth Concert Band - America at 250: Our Shared Soundtrack 

The Rehoboth Concert Band brings a meaningful and community-driven performance to Coastal Delaware with America at 250: Our Shared Soundtrack, a concert series celebrating the 250th anniversary of the United States. 

Made up of instrumentalists of all ages and skill levels, including both adults and talented youth from surrounding communities, the band creates a collaborative and inclusive musical experience that reflects the spirit of the area. 

Their repertoire spans a wide range of styles, from classical and contemporary pieces to show tunes, film scores, marches, and traditional concert band favorites, making each performance feel both familiar and dynamic. 

Beyond the music itself, the group is known for its commitment to artistic growth and community enrichment, often partnering with local organizations and participating in events that support charitable causes. 

These outdoor performances, set in locations like the Rehoboth Beach Bandstand and Stango Park in Lewes, offer a relaxed and accessible way to experience live music while also taking part in a larger celebration tied to the country’s history.

• Dates: May 27th-June 2nd
• Locations: Milton Memorial Park, Rehoboth Beach Bandstand & Lewes Stango Park

Image courtesy of Milton Theatre

Nunsense II: The Second Coming at Milton Theatre

Nunsense II: The Second Coming brings the Little Sisters of Hoboken back to the stage at Milton Theatre with even more energy, humor, and theatrical flair. 

Set just six weeks after their original benefit show, the sisters return to put on a “thank-you” performance for their supporters, but this time, they are a little more polished after catching the theater bug. 

Of course, things do not stay simple for long, as the show quickly turns into a series of hilarious and chaotic moments, from unexpected visitors arriving to claim one of the sisters to the added pressure of performing in front of a talent scout. 

With music, comedy, and plenty of over-the-top antics, the production includes standout moments like a lively bingo game led by Sister Mary Amnesia, playful musical numbers such as “What Would Elvis Do?”, and a high-energy finale that ties everything together. 

It is a lighthearted and entertaining show that leans fully into its humor while still delivering a fun, engaging experience for the audience.

• Dates: April 30th-May 17th
• Address: 110 Union Street, Milton

Matteo Bocelli - Falling In Love World Tour at Freeman Arts Pavilion

Matteo Bocelli’s Falling In Love World Tour makes a stop at Freeman Arts Pavilion as part of the venue’s grand opening of its new permanent home, bringing an internationally recognized artist to Coastal Delaware for a standout live performance. 

As the son of legendary tenor Andrea Bocelli, Matteo steps into the spotlight with a unique balance of honoring his musical roots while carving out his own identity as a modern artist. 

His second album, Falling In Love, showcases that evolution, blending classical influence with contemporary pop through songs that focus on emotion, vulnerability, and storytelling. 

Rather than relying on fast trends, his music leans into themes of longing, romance, and personal reflection, with tracks that range from intimate ballads to more upbeat, expressive pieces. 

Matteo has collaborated with well-known songwriters and brings a strong sense of musicianship to his work, not only as a vocalist but also as a pianist and songwriter. 

His live performance offers a mix of that emotional depth and polished stage presence, creating a concert experience that feels both personal and elevated, while also marking an exciting moment for the Freeman Arts Pavilion as it opens its new space.

• Date: July 8th
• Address: 31806 Lake View Drive, Selbyville

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There is always something new happening across Coastal Delaware, so make sure to keep checking back with us for more updates on upcoming shows, events, and everything happening around the area!

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