The holiday season is one of the most exciting times of the year at Milton Theatre, where the lineup is packed with performances that bring cheer, nostalgia, and plenty of local talent to the stage. 

Whether you love timeless holiday music, immersive family experiences, or festive shows with a creative twist, the theater offers something for every age and interest!

Joseph & the Amazing Technicolor Dreamcoat

A vibrant, song-filled retelling of the biblical story of Joseph, this beloved musical bursts with humor, heart, and an unforgettable mix of musical styles, from country-western to calypso to sweeping ballads. 

Guided by the Narrator, audiences follow Joseph through betrayal, adventure, and triumph as he discovers his gift for interpreting dreams and changes the fate of an entire nation. 

Full of iconic numbers like “Any Dream Will Do” and “Close Every Door,” this production brings timeless storytelling to life with color, energy, and family-friendly magic.

• Dates: December 10th-14th
• Hours: Shows at 2pm and 7:30pm

Polar Express Pajama Party & Film Screening

This cozy holiday experience invites guests to arrive in pajamas and enjoy a heartwarming screening of The Polar Express, complete with festive treats available for purchase. 

The beloved animated film follows a skeptical young boy on a magical journey to the North Pole, discovering the true spirit of Christmas along the way. 

With two screening times, at 10am and at 6pm, this event creates a warm, nostalgic atmosphere perfect for families and believers of all ages.

• Date: Sunday, December 14th
• Hours: Screenings at 10am and 6pm

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Cartoon Christmas Trio

Celebrate the nostalgia of classic holiday cartoons with the Cartoon Christmas Trio, performing the iconic Vince Guaraldi Peanuts score note-for-note using the original instrumentation. 

Joined by the Milton Theatre’s Musical Theatre Ensemble, the trio also features music from favorite cartoons like Rudolph, The Grinch, and Frosty. 

This cherished jazz tradition blends expert musicianship with the warmth and whimsy of childhood holiday memories.

• Date: Wednesday, December 17th
• Hours: Starts at 7pm

Slay Belles: A Holiday Drag Show

A fabulous and festive night of drag entertainment, Slay Belles brings glitter, comedy, and fierce holiday performances to the stage under the sparkling guidance of Magnolia Applebottom. 

Featuring Alondra Sanchez and Roxy Overbrooke, this show mixes powerhouse vocals, dazzling looks, and playful holiday sass. 

It’s a joyful, high-energy celebration designed to make spirits bright and audiences cheer. 

With its blend of glamorous theatrics and hilarious holiday twists, it’s a beloved Milton Theatre tradition audiences return to year after year.

• Date: Friday, December 19th
• Hours: Starts at 7:30pm

Front Porch Orchestra’s Bluegrass Nutcracker

Tchaikovsky’s iconic Nutcracker suite gets a lively bluegrass makeover in this inventive performance by Front Porch Orchestra. 

With rich acoustic instrumentation and virtuosic arrangements, the group transforms familiar holiday melodies into something fresh, warm, and irresistibly rhythmic. 

It’s a charming fusion of classical tradition and bluegrass soul that delights music lovers of all kinds. 

Each movement is performed bar-for-bar from the original score, offering a faithful yet refreshingly imaginative take on a timeless holiday classic.

• Date: Saturday, December 20th
• Hours: Starts at 1pm

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Sinatra’s Christmas with Tony Sands

Step into a world of elegance and nostalgia as Tony Sands channels the legendary Frank Sinatra, serenading audiences with smooth, iconic hits from the Chairman of the Board.

Backed by the full band SWINGTOPIA, this performance captures the essence of the Swing Era, transporting listeners to a bygone era of sophistication and style. 

With over 30 years perfecting his craft and acclaimed as the #1 Sinatra vocalist in the country, Sands delivers a show that is both heartfelt and unforgettable.

• Date: Saturday, December 20th
• Hours: Starts at 7:30pm

Holiday Tea: Interactive Live Show

Enjoy a magical holiday experience with tea, cookies, and live entertainment from your favorite holiday characters! 

With morning and afternoon sessions, this interactive show brings singing, dancing, and storytelling to life, pulling the entire audience into the fun. 

Afterward, kids can meet the characters and snap photos during a special meet-and-greet.

Presented by the Milton Theatre’s “Triple Threat” musical theatre students, this festive event is perfect for little ones and families seeking a charming, hands-on holiday celebration.

• Date: Sunday, December 21st
• Hours: Shows at 11am and 2pm

Chesapeake Silver Cornet Brass Band Holiday Concert

Experience the grandeur of the holiday season with Delaware’s only 35-piece all-brass concert band, performing in the historic British Brass Band tradition. 

The Chesapeake Silver Cornet Brass Band delivers a captivating mix of light classics, marches, swing, big band, and blues, steeped in both musical excellence and community spirit. 

This all-volunteer ensemble from the Mid-Atlantic region brings joyous energy, humor, and education to a festive concert that appeals to music lovers of all ages.

• Date: Sunday, December 21st
• Hours: Starts at 7pm

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Milton’s Merry Melodies: A Hometown Holiday Cabaret

Celebrate the season with cherished local performers in a heartwarming cabaret full of music, joy, and nostalgia. 

Milton’s Merry Melodies blends classic holiday songs with fresh interpretations, performed by an ensemble whose voices capture the spirit of the season. 

This community-centered show invites audiences to share in festive cheer and create lasting holiday memories, with two performances, one at 2pm and the other one at 7pm, for maximum enjoyment.

• Date: Monday, December 22nd
• Hours: Shows at 2pm and 7pm 

Duke Ellington’s The Nutcracker Suite by Delmarva Big Band

Witness the magic of Duke Ellington’s jazz interpretation of The Nutcracker Suite, performed live by the 18-piece Delmarva Big Band. 

Combining brass, woodwinds, and a full rhythm section, this performance blends breathtaking solos, intricate harmonies, and irresistible rhythms that will make audiences move and groove. 

Experience the passion, skill, and joyous energy of this world-class ensemble as they bring Ellington and Strayhorn’s iconic arrangements to life.

• Date: Tuesday, December 23rd
• Hours: Starts at 7pm

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