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Annapolis is a city of the arts. Few modest-sized cities in the United States can claim a symphony, an opera, live theater, dance, and more. To highlight the breadth of the city’s cultural offerings, we have created a synopsis of its rich artistic landscape, focusing primarily on those venues that engage professional performers.
There are, however, ongoing needs. One of the greatest, according to April Nyman, Executive Director of the Arts Council of Anne Arundel County, is space—space for performing, rehearsal, and storage. Such facilities require substantial funding, which is an investment in the city.
You will notice this list focuses primarily on the performing arts. The Mitchell Art Museum is increasingly bringing thought-provoking contemporary art to both the college and the city, a much-needed addition to the visual arts scene. With support from St. John’s College and Annapolis Home Magazine, poetry and the literary arts have also taken a big leap forward through “Poets in Conversation Room,” conceived by poets Grace Cavalieri and Kymberly Taylor and held at St. John’s.
A city of the arts requires many highly trained performers, skilled administrators, and audiences who fund and attend its events. We, the audience, do more than purchase tickets and attend performances; through our participation, we are, in effect, the stewards of the arts. Each generation is given this gift: to carry the arts forward and keep them alive. – Robert Haywood
Founded in 2013 by filmmakers K. Lee Anderson and Patti White, the Annapolis Film Festival was created to bring world-class independent cinema to the heart of Maryland’s capital city. What began as a grassroots effort has grown into one of the region’s most anticipated cultural events, welcoming more than 10,000 attendees annually and showcasing over 70 films from around the world. Over the years, AFF has hosted award-winning filmmakers, industry leaders, and emerging voices, while building a reputation for meaningful conversations, diverse storytelling, and community engagement. Today, the festival is recognized nationally and has been named one of the “25 Coolest Film Festivals in the World” by MovieMaker Magazine. Filmmakers have come from as far away as Iceland, Brazil, Romania, Kazakhstan, and the Australian Outback.
Annapolis Opera has been presenting critically acclaimed operas, concerts, and arts education programs for 54 years, leading the way in accessible performing arts in the community. With a rich history of artistically exceptional opera programming and offering enlightening educational experiences, the Opera continues to play a pivotal role in fostering the growth of emerging performing arts professionals. As a community cultural asset and collaborative partner, the Annapolis Opera is dedicated to promoting opera as an art form, making it a cherished source of both insight and appreciation for enthusiasts and newcomers alike.
Dates: October 30 and November 1, 2026 | Place: Maryland Hall, Annapolis, MD
For details, visit www.annapolisopera.org
Outdoors, under the stars, Annapolis Summer Garden Theatre has been entertaining the community with live theatre since 1966. This summer, they plan a season of three Broadway musicals and a special September show to celebrate their 60th anniversary.
At a time when other theatres were dark, ASGT was founded by a group of civic-minded Annapolitans with a dual purpose: to bring live theatre to the city and to provide college students coming home for the summer an opportunity to be involved in theatre. The first season was performed on a makeshift stage behind the Carvel Hall Hotel. Shortly after that season, when that stage was demolished to reveal the William Paca House, they relocated to their current home on Compromise Street. Because performances are outdoors across from the city dock, you might experience a duck flyover or a boat horn during a performance.
Dates: September 11–13 and September 17–19, 2026 | Place: Annapolis Summer Garden Theatre, Annapolis, MD
For details, visit www.summergarden.com
The Annapolis Symphony Orchestra (ASO), founded in 1962, is the premier professional orchestra serving Maryland’s capital region. The orchestra has a roster of 70+ professional tenured musicians, all of whom are union-represented. As the ASO embarks on its 65th season, concerts at Maryland Hall, The Music Center at Strathmore, and Joseph Meyerhoff Symphony Hall will showcase classical music, pops concerts, Holiday Pops, and performances designed for school-aged children. The ASO reaches thousands through concerts, education programs, and community partnerships across Anne Arundel County. Under the leadership of Music Director José-Luis Novo, now in his 21st year as artistic director, the orchestra brings world-class guest artists and a varied repertoire of iconic classical pieces and new composers to Annapolis audiences. Beyond the stage, the ASO is deeply committed to music education, serving students and families throughout the region through the Annapolis Symphony Academy. A little-known fact: the academy helps students overcome financial barriers by making participation in all ensembles tuition-free.
Date & Place: September 5, 2026, at Downs Park | Date & Place: September 6, 2026, at Quiet Waters Park
For details, visit www.annapolissymphony.org
Established in 1992, the Arts Council of Anne Arundel County is dedicated to cultivating and promoting a vibrant arts community. The Council’s grants, educational programs, exhibits, and events strengthen the county’s cultural fabric. With over $900,000 in funding distributed annually to nonprofit art organizations and schools, the Council nurtures the continued growth of the county’s creative sector.
Since 2000, the Annie Awards have celebrated individuals making meaningful contributions to arts and cultural organizations.
Date: October 5, 2026 | Place: Maryland Hall, Annapolis, MD
For details, visit www.acaac.org
Since 1978, Ballet Theatre of Maryland has established an Annapolis home for professional dancers drawn from across the country and around the world. As the state’s premier ballet company, BTM stages over 20 full-length performances each year while also cultivating the next generation of dancers and dance enthusiasts.
The impulsive young Scotsman James falls for an ethereal sylph on the morning of his wedding. James must choose between
the sylph and his human bride-to-be, drawing the ire of a vengeful witch.
Dates: October 16–18, 2026 | Place: Maryland Hall, Annapolis, MD
For details, visit www.balletmaryland.org
Since 1959, Children’s Theatre of Annapolis (CTA) has provided high-quality theatre arts education and productions for youth ages 5–18 across central Maryland. CTA is a community-based nonprofit grounded in creativity, teamwork, leadership development, and the belief that every child deserves the chance to shine onstage and behind the scenes. CTA serves both the child and the community by offering accessible, transformative arts experiences that foster confidence, collaboration, and connection. CTA believes in the power of the performing arts to bring people together and in providing meaningful opportunities for individuals of all backgrounds to participate, learn, and thrive.
Dates: October 30–November 15, 2026 | Place: Children’s Theatre of Annapolis, Annapolis, MD
For details, visit www.childrenstheatreofannapolis.org
In a city rich with maritime history and cultural charm, Classic Theatre of Maryland stands as a defining force in Annapolis’s arts scene. Known for pairing literary depth with polished production values, the company brings enduring works to life through nuanced performances and inventive staging. The professional talent—actors, directors, and designers—brings a level of artistry and precision that is unparalleled in the region, elevating every production. Its intimate setting invites audiences into the heart of the story while expanded cabarets, special events, and artist talkbacks create a vibrant theatrical community beyond the stage. With year-round programming and a clear commitment to excellence, it has become the destination where discerning theatergoers gather, season after season.
Revenge. Betrayal. Ghosts. Step into the shadows of Denmark in this thrilling new production of Shakespeare’s greatest tragedy. Prince Hamlet faces a corrupt court, unraveling secrets, and deadly loyalties—where the line between truth and illusion is razor-thin.
Dates: Oct 1–18, 2026 | Place: Classic Theatre of Maryland, Annapolis, MD
For details, visit www.classictheatremaryland.org
Compass Rose Theater, the award-winning professional teaching theater company in Annapolis, was recently honored with several Helen Hayes Award recommendations for its productions of Rent, Annie, Little Shop of Horrors, and Proof. Last year, Compass Rose Theater’s production of The 25th Annual Putnam County Spelling Bee earned seven Helen Hayes Award nominations. As part of its educational mission as a nonprofit theater, Compass Rose regularly includes youth- and family-oriented productions in its schedule. Recent examples include Annie, The Complete Works of William Shakespeare (Abridged), and Alice in Wonderland.
Dates: September 18–October 11, 2026 | Place: Live Arts Maryland in the Annapolis Mall, Annapolis, MD
For details, visit www.compassrosetheater.org
Are you curious and open-minded? Interested in expanding your understanding of art? Then you might check out the Elizabeth Myers Mitchell Art Museum at St. John’s College, Annapolis (also known simply as “/m”). There, you will find a snazzy micro-cinema for video art, as well as exhibitions that fill you with more questions than answers—which, if you think about it, is what good art should do.
Spurred by a 600-year-old Liberty Tree that once stood on St. John’s College’s front lawn, the community-driven exhibition will produce a prototype for an Annapolis Liberty Tree Monument.
Date: Fall 2026 | Place: Elizabeth Myers Mitchell Art Museum, Annapolis, MD
For details, visit www.sjc.edu/mitchell
Live Arts Maryland is a nonprofit performing arts organization dedicated to enriching the cultural life of Annapolis and the surrounding region through choral, orchestral, and innovative performance programming. Founded through the legacy of the Annapolis Chorale and later expanded to include the Annapolis Chamber Orchestra, Cantori, and the Bach+ Series, Live Arts Maryland brings together professional artists, community musicians, and emerging talent.
In addition to mainstage concerts at Maryland Hall, St. Anne’s Episcopal Church, and other venues, Live Arts Maryland operates the Live Arts Studio at the Annapolis Mall. There, it presents its own cabaret series and serves as a creative performance and rehearsal hub for artists and arts organizations throughout the region.
Live Arts Maryland’s popular Broadway in Annapolis concert celebrates the music of the Broadway stage with powerful performances by the Annapolis Chorale and the Annapolis Chamber Orchestra.
Dates: October 9–10, 2026 | Place: Maryland Hall, Annapolis, MD
For details, visit www.liveartsmd.com
MFA hosts 40+ professional exhibitions featuring works by local, national, and international living artists across all media. More than 2,600 works of art are shared with the public at MFA’s Circle Gallery in downtown Annapolis, online, and through other sites. Through Paint Annapolis, the city’s largest visual arts event, MFA brings artists and art lovers from North America and Europe to the city to celebrate the artistic practice of capturing the beauty of the Chesapeake area. Operating for almost 60 years, MFA connects the public with artists at all stages of their careers who are expanding community consciousness through their work.
Paint Annapolis is a week-long premier plein air painting event that puts more than 100 artists on the streets of Annapolis to interpret our historic town in watercolor, oil, acrylic, and pastel. The work is displayed and celebrated throughout the week, with MFA providing $18,500 in awards.
Date: May 31–June 7, 2026 | Place: Downtown Annapolis, Annapolis, MD
For details, visit www.mdfedart.com
Maryland Hall is where the arts become part of everyday life in Annapolis. From world-class performances and thought-provoking conversations to hands-on classes and rotating gallery exhibitions, the Hall offers something to return to again and again. You might spend an evening in the theatre, discover a new artist in our galleries, or try your hand at something creative for the first time. As a cornerstone of the region’s cultural landscape, Maryland Hall brings together artists, audiences, and ideas, creating a space where creativity feels elevated, personal, and at home.
This fall, Maryland Hall Presents brings Ailey II to Annapolis for an unforgettable evening of contemporary dance, blending rising talent with bold, expressive choreography rooted in the legacy of Alvin Ailey.
Date: October 11, 2026 | Place: Maryland Hall, Annapolis, MD
For details, visit www.marylandhall.org
The Naptown Philharmonic Orchestra has been a vibrant part of the Annapolis arts community for over 20 years. Founded as the Londontowne Symphony Orchestra with a passion for accessible, high-quality live music, it has grown into a dynamic cultural force, blending beloved masterworks with innovative contemporary programming. Today, the orchestra thrives through collaborations with local schools, arts groups, and community organizations, enriching audiences of all ages.
Through educational outreach and inspiring performances, the Naptown Philharmonic fosters a lifelong love of live symphonic music. It provides opportunities for professional, student, and community musicians to learn and grow under the guidance of experienced leaders.
Celebrate Hispanic Heritage Month with the Naptown Philharmonic Orchestra.
Date: September 19, 2026 | Place: Maryland Hall, Annapolis, MD
For details, visit www.naptownphil.org
The Colonial Players isn’t just a theatre—it’s a little slice of Annapolis magic. Tucked right downtown, it’s intimate, welcoming, and unlike anywhere else you’ve likely seen a show. With its in-the-round stage, you’re never more than a few feet from the action, which means you don’t just watch a play—you feel it alongside the actors.
Whether you’re a theatre regular or haven’t been in years, you’ll find something at CP to surprise you, challenge you, make you laugh, or move you. These are stories brought to life by your neighbors: teachers, students, veterans, artists, accountants—people who believe in the power of live theatre to connect us.
Date: September 2026 | Place: The Colonial Players, Annapolis, MD
For details, visit www.thecolonialplayers.org
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The Faces of Annapolis 2026