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Music, Theater, and Film: Exploring the Cultural Side of Annapolis

From prestigious symphonies and opera on the hallowed stage at Maryland Hall to world-class community theater and a film festival that could rival Cannes, Annapolis cultural attractions will entertain, dazzle, and impress – and they’re all just a few minutes from our Annapolis bed and breakfast.

Maryland Hall – Where the Annapolis Symphony and Opera Gloriously Resound

conductor leading the orchestra

On almost any weekend of the year, Maryland Hall is where the cultural conversation is happening, as it’s the home stage for both the Annapolis Symphony Orchestra and Annapolis Opera. Since the late 1970s, when the Hall converted a former high school into a stunning performance space – including the main theater, with its massive windows, fantastic views from every seat, and world-class sound; a smaller black box theater; and outdoor spaces for summer shows – their mission has been to share “art for all” and lift the community, exemplified by their Academy program which trains and supports local high-schoolers learning classical music.

The symphony performs in the main theater at Maryland Hall a few times monthly, alternating between different classical styles and eras, under the brilliant direction of Musical Director Jose-Luis Novo, who has held the baton for almost 20 years. Catch their March 1-2, 2024, Masterworks performance, which features a Romantic era piece from Berlioz, the famous Enigma Variations by Elgar, and Schumann’s passionate Cello Concerto. On April 12-13, the next edition of their Masterworks series includes Italian composer Respighi’s sprawling Roman Festival piece, Beethoven’s final piano concerto, and a newly commissioned world premiere from modern composer Nicky Sohn, demonstrating the symphony’s desire to highlight both classical and contemporary music.

The Annapolis Opera, the first resident company to settle in Maryland Hall over four decades ago, has several unique shows in the coming months. They will perform the Elixir of Love, an early 19th-century opera with a lighthearted romantic theme, on the evening of March 15th and a matinee on March 17th, 2024. To take a deeper dive into the musical history of the opera, attend their “Opera Insights” event on Feb 24th, when the opera’s artistic director leads a free lecture about Italian composer Donizetti and how he crafted his career-defining score. In the spring, don’t miss the always-popular Opera Vocal Competition on May 5th, which celebrates its 36th year of showcasing the country’s finest opera voices. It’s free, open to the public, and quite fun for the audience, as you’ll get to vote for your favorite singer in the audience choice award. Last year’s winner, Winona Martin, became the lead mezzo-soprano for the Washington National Opera soon after. Other recent winners have gone on to sing with the Chattanooga Opera and the New York Metropolitan Opera and amaze the audience at Carnegie Hall, speaking to the quality of Annapolis cultural attractions and the range of performers who regularly grace the stage at Maryland Hall.

Annapolis Cultural Attractions: Where the Masks of Tragedy and Comedy Take a Bow in Theater

One of the touchstones of the Annapolis cultural space is just a couple blocks away, where the Colonial Players have been performing top-tier community theater for decades. A non-profit and volunteer-driven outfit, they celebrate their 75th anniversary in 2024, having converted an old car garage into an intimate 180-seat theater space. Every seat is near the stage, designed in the round, and even the front-row tickets are very reasonable at less than $30 each. The Players’ production calendar is impressive, ranging from zany comedies to intense dramas and their always-anticipated holiday performance of The Christmas Carol every December. 

Their season, a highlight of Annapolis cultural attractions, consists of 6 plays yearly, beginning in September and wrapping up in the spring, after which they take a summer break from the stage. They will perform two plays in the coming months, each running for 3-4 weeks, Thurs-Sun. From March 1-30, 2024, check out their performance of the romantic musical The Baker’s Wife, a charming story about a French village that comes together to reunite the town baker and his wife. Later in the spring, from April 26th through May 18th, they will perform the theatrical adaptation of the award-winning novel The Curious Incident of the Dog in the Nighttime, a detective story told from the perspective of a 15-year-old math savant trying to solve the mystery of the fate of a neighbor’s beloved dog.

In addition to the Colonial Players, several other local theater companies will bring productions to nearby stages in the coming months. Although a relative newcomer on the scene, having formed just over a decade ago, the Compass Rose Theatre has quickly established itself as one of the most respected stage outfits in the city. With a guiding motto to “inspire and enlighten,” their mission is to perform masterfully and bring up the next generation of Annapolis talent through their Young Actor’s Studio. During March and April of 2024, catch their upcoming performance of the 25th Annual Putnam County Spelling Bee, a Tony Award-winning story about teens vying for a spelling championship and the ensuing hilarity. As of 2022, their theatrical home is at Maryland Hall, where they share the stage with the symphony and opera. 

Every summer, the stage comes alive under the stars at the Annapolis Summer Garden Theatre’s outdoor performance space at City Dock. Just two blocks from our location and right on the waters of Spa Creek, attending one of their captivating musical theater productions on a warm Maryland summer night is a dream for theater enthusiasts. Their 2024 season kicks off on May 23rd with the Prom, about Broadway stars commanding a small-town school dance, followed in June and July by Escape to Margaritaville, a touching tribute to Jimmy Buffet, and finishing the summer with Big Fish, a larger-than-life tale made famous by the beloved Tim Burton film adaptation.

comedy and tragedy masks on the stage

Like the Compass Rose and Summer Garden Theater, the Children’s Theatre of Annapolis is a non-profit operation driven to create community and foster local theater arts. Their theater workshops and productions initially occurred in local elementary schools, growing over the past 60 years. Since 2008, their home stage has been a top-notch modern performance space in Yorktown’s Bay Head Park, just a 15-minute drive east of downtown Annapolis. From May 3-19, 2024, bring the whole family to their musical production of The Descendants, a wildly entertaining story of the teenage kids of Disney villains going to school alongside the offspring of beloved Disney heroes and heroines.

Following a memorable evening of local theater, stroll a block over on State Circle – a historic landmark in downtown Annapolis, as it surrounds the Maryland State House, which is nearly 250 years old – and onto Maryland Ave for some late-night food and drinks at the classic Galway Bay Irish Pub. Local musicians perform every Friday and Saturday night until 11 pm, and it’s a lively atmosphere, much like stepping into a neighborhood spot in Dublin. Share some Irish curry fries and cream chocolate mousse while sipping one of their 20+ rare whiskeys, a perfect nightcap after an entertaining evening.

movie theater

Annapolis Film Festival – A Celebration of Moviemaking Throughout the City

With films like Patriot Games and Syriana shot on location at the US Naval Academy and actors such as Edward Norton, Robert Mitchum, Jada Pinkett Smith, and John Waters cutting their teeth in Maryland, it’s no surprise that our city has a rich film heritage. Movie buffs will love the upcoming 12th year of the Annapolis Film Festival, from April 4 to April 7, 2024, with a program of over 70 films, ranging from short films to documentary and narrative features.

The festival starts with an opening night screening and late-night party where you can hobnob with film industry folks and fellow festival attendees. The buzz continues through the weekend with filmmaker panels, Q and A sessions, and an awards show on the final day, all included with a festival general pass. 

After a festive day of downtown screenings and film events, head around the block from your Annapolis Inn suite to the upstairs lounge at Harry Browne’s, where the classy ambiance is lovely for sharing a bottle of wine and discussing your favorite scenes from the day’s films.

Although exact feature film programming and screening times are still in flux, check in the coming weeks for updated info on their selections. Leading up to the festival weekend, don’t miss the monthly movie screenings at Maryland Hall’s tiny black box theater space, put on by the Annapolis Film Society. These films align with their goal of “igniting, inspiring, and entertaining” while promoting diverse viewpoints and challenging the viewer to think deeply.

Stay with us, where the finest Annapolis cultural attractions await!