Looking for something different to do this fall? From Broadway musicals and classic plays to stand-up comedy and live music, there are plenty of performances worth adding to your calendar. Whether you’re planning a family outing, date night or evening with friends, check out these upcoming fall shows in Annapolis and the surrounding area.
Hamlet
Oct. 15-18 | Classic Theatre of Maryland, Annapolis
Shakespeare’s classic tragedy follows Prince Hamlet as he seeks revenge for his father’s murder. Filled with betrayal, family drama and suspense, this timeless production explores the consequences of revenge and the struggle between right and wrong.
Josh Blue
Oct. 15 | Rams Head on Stage, Annapolis
Comedian Josh Blue, winner of NBC’s Last Comic Standing and finalist on America’s Got Talent, brings his quick wit, improvisation and personal stories to Annapolis for a night of stand-up comedy. Stephen Agyei joins him for the show.
La Sylphide
Oct. 16-18 | Maryland Hall, Annapolis
Ballet Theatre of Maryland presents this romantic ballet set in the Scottish Highlands. When a young man falls under the spell of a mysterious woodland spirit, he abandons his wedding plans to follow her into an enchanted world. Expect beautiful choreography, supernatural twists and a story of love and longing.
Boney James
Oct. 17 | Rams Head on Stage, Annapolis
Four-time Grammy-nominated saxophonist Boney James brings his signature blend of smooth jazz, R&B and soul to the stage. Known for his melodic sound and energetic performances, James offers an evening of music for jazz lovers.
Moms Unhinged
Oct. 18 | M&T Bank Exchange, Baltimore
Motherhood is hilarious, exhausting and sometimes completely unhinged. This stand-up comedy show tackles everything from raising kids and marriage to midlife crises and dating. It’s a night of relatable humor for moms who could use a good laugh. For ages 18 and older.
Ignite Annapolis #7
Oct. 20 | Maryland Hall, Annapolis
Get inspired by local speakers sharing big ideas in just five minutes each! This fast-paced event features 15 speakers covering a variety of topics, with only 20 slides per presentation. Expect thought-provoking stories, fresh perspectives and plenty of inspiration.
James Austin Johnson
Oct. 21 | Rams Head on Stage, Annapolis
Saturday Night Live cast member James Austin Johnson brings his comedy and celebrity impressions to Annapolis. Known for his impersonations and memorable sketches, Johnson promises a night of laughs.
The Legend of Sleepy Hollow
Oct. 23-Nov. 8 | The Colonial Players, Annapolis
Just in time for Halloween, Washington Irving’s classic tale comes to life with a mix of spooky suspense and humor. Follow schoolteacher Ichabod Crane as he navigates romance, small-town gossip and the terrifying legend of the Headless Horseman.
SIX: The Musical
Oct. 25-Nov. 1 | Hippodrome Theatre, Baltimore
The six wives of Henry VIII take the microphone in this high-energy Broadway musical that turns Tudor history into a pop concert. Featuring catchy songs, dazzling costumes and plenty of attitude, SIX gives these famous queens a chance to tell their own stories.
Halloween Whodunit 3
Oct. 29 | Rams Head on Stage, Annapolis
Part murder mystery, part comedy show, this interactive Halloween performance invites audiences to enjoy an evening of laughs and mystery. Follow the clues, meet the suspicious characters and see if you can figure out whodunit!
Disney’s Frozen
Oct. 30-Nov. 15 | Children’s Theatre of Annapolis, Annapolis
The beloved Disney movie comes to life onstage with Anna, Elsa, Olaf and all your favorite characters. Featuring familiar songs such as “Let It Go” alongside new music written for the Broadway production, this family-friendly musical celebrates sisterhood, love and finding the courage to be yourself.
Gaelic Storm
Nov. 4-5 | Rams Head on Stage, Annapolis
Get ready for a lively mix of Celtic rock, traditional Irish music and energetic storytelling. Known for their appearance in the movie Titanic, Gaelic Storm brings infectious rhythms and spirited performances that will have audiences tapping their feet.
Makaya McCraven
Nov. 8 | Maryland Hall, Annapolis
Jazz drummer, composer and producer Makaya McCraven brings his innovative sound to Annapolis as part of the Annapolis Jazz & Roots Festival. Blending jazz with hip-hop influences, improvisation and modern rhythms, McCraven offers a fresh take on traditional jazz.
Jesse Cook
Nov. 17 | Rams Head on Stage, Annapolis
Acclaimed guitarist Jesse Cook brings his blend of flamenco, jazz and world music to the stage. Known for his impressive guitar skills and rhythmic performances, Cook delivers an evening of instrumental music with international influences.
Hell’s Kitchen
Nov. 17-22 | Hippodrome Theatre, Baltimore
Inspired by the life and music of Alicia Keys, this Broadway musical follows a 17-year-old girl growing up in New York City as she discovers her passion for music and searches for independence. Featuring Alicia Keys’ biggest hits and original songs, Hell’s Kitchen is a coming-of-age story about family, dreams and finding your voice.
The Nutcracker
Nov. 22 and Dec. 12-20 | Ballet Theatre of Maryland, Annapolis
Celebrate the holiday season with this beloved ballet featuring Clara, the Sugar Plum Fairy and the magical Land of Sweets. With festive costumes, beautiful dancing and Tchaikovsky’s familiar score, The Nutcracker is a holiday tradition for the whole family.
Looking for even more live entertainment? Check out the full Rams Head on Stage calendar for additional concerts, comedians and performances throughout the season. Stay tuned for our holiday performances next month!
Annapolis Moms Deal Drop | Oct. 15, 2026