Entertainment & Events in Annapolis, Maryland

Special Events

Anne Arundel County Fair 410-923-3400
1450 Generals Highway
Annapolis, MD 21032
Anne Arundel County Fairgrounds
This fairground is host to the county fair that features agricultural exhibits, farm and garden displays, home crafts, art, 4-H exhibits, and food booths, as well as other events such as Bluegrass festivals, crafts shows, demolition derbies, tractor pulls, and more. more
Christmas in Annapolis and Anne Arundel County 410-280-0445
26 West Street
Annapolis, MD 21401
One can experience the true holiday magic of Annapolis and Anne Arundel County each holiday season through this festival that includes caroling, tree lightings, the arrival of Santa Claus, the greening of the city, concerts, ballet, theatre, and other special holiday events throughout the month of December. more
Eastport Yacht Club Lights Parade 410-263-0415
Eastport Dock
Sponsored by the Eastport Yacht Club, this is Maryland’s oldest lighted boat parade, and features over seventy lighted sail and power boats; the event is held for the holiday season in December, and one should contact the organizers as to specific dates. more
First Night Annapolis 410-268-8553
100 Cathedral Street
Annapolis, MD 21401
City Dock
Each December thirty first, Annapolis is transformed into a theatre without walls or boundaries, as hundreds of performers practice their arts all throughout the downtown area; this bringing of people together through the arts begins early with programs geared towards the entertainment of children, and ends with a waterfront fireworks finale.
Fourth of July Celebration 410-263-1183
160 Duke of Gloucester Street
Annapolis, MD 21401
Annapolis celebrates Independence Day with an old fashioned parade that is followed by a concert performance from the United States Naval Band, which is accompanied by a spectacular waterfront fireworks display.
Annapolis Holiday Stroll 410-280-0445
26 West Street
Annapolis, MD 21401
The Annapolis Holiday Stroll consists of such activities as caroling, tree lightings, a visit from Santa Claus, historic house tours, ballet, concerts, theatre, and many other holiday events throughout the month of December. Special privileges are offered by participating shoppes, restaurants and hotels. more
Mid-Atlantic Wine Festival 410-280-3306
P.O.Box 2983
Annapolis, MD 21404
This festival features the best in wine, beer, food and music of the Mid-Atlantic region; continuous live entertainment and a plethora of arts and crafts booths are integral parts of the event. more

Concerts & Performances

Annapolis Chorale 410-263-1906
801 Chase Street
Annapolis, MD 21401
Maryland Hall for the Creative Arts
The Annapolis Chorale strives to strengthen and elevate the life and culture of the community through presenting a variety of first rate concerts, performances, and productions; also included under the aegis of the chorale are the Chamber Chorus, the Chamber Orchestra, and the Annapolis Youth Chorus. In addition to those performances that are of a more Classical nature, the organization at times presents musicals such as “The Music Man,” and other family oriented productions and concerts. more
Annapolis Symphony Orchestra 410-263-0907
801 Chase Street
Annapolis, MD 21401
Maryland Hall for the Creative Arts
The Annapolis Symphony presents the best in Classical concerts, as well as an annual Holiday Pops Concert in December; many of the best and brightest conductors and soloists are featured in the concerts presented by this fine organization. The orchestra is also known for its free Labor Day Weekend Concert in the Park.
Ballet Theatre of Maryland 410-263-8289
801 Chase Street
Annapolis, MD 21401
This prestigious ballet company presents the best in ballet productions and offers excellent educational and training courses. Seasonal productions for occasions such as Halloween and Christmas are offered, as well as other presentations that relate to certain themes, such as Latin romance, or the American Classics series that presents ballet adaptations of such literary works as “The Scarlet Letter.”
Maryland Hall for the Creative Arts 410-263-5544
801 Chase Street
Annapolis, MD 21401
The Maryland Hall For The Creative Arts presents productions and concerts that include such varied genres as Chorale, Symphony, Opera, and Ballet Theatre; classes in the performing and visual arts are offered, and the Air and Cardinal Galleries exhibit the finest in local and regional contemporary art. more
Annapolis Opera 401-267-8135
801 Chase Street
Annapolis, MD 21401
One can hear rising young stars signing the greatest operatic works at the concerts staged by this world-class opera company. more
Annapolis - Songs of the Sea - Concert Series 410-263-7837
80 Compromise Street
Annapolis, MD 21401
Listen to original Chesapeake Bay Music while sailing aboard a classic, wooden schooner on a fantastic sunset sail. This acoustic concert series is in conjunction with the Annapolis Maritime Museum and their Chesapeake Music Institute. Raise the sails, steer the boat or sit back and relax on a two-hour sail while enjoying a different musical guest every Thursday. See link under "Attractions - Tours & Cruises."

Plays & Productions

Annapolis Summer Garden Theatre,Inc 410-268-9212
143 Compromise Street
Annapolis, MD 21401
Historic District
This two-hundred-seat outdoor community theatre is located in the courtyard of the old city blacksmith shop in the City Dock area; three productions are offered between the last week in May and the first week in September. more
Colonial Players, Inc. 410-268-7373
108 East Street
Annapolis, MD 21401
A wide variety of dramatic productions are brought to the heart of downtown Annapolis by this theatre group that was founded in 1949 in order to bring fine theatre to Annapolis; the typical season, consisting of five productions, feature a variety of styles including classics, contemporary comedies, musicals, dramas, plays by new and upcoming playwrights, experimental theatre, and theatre for children. There is also a host of workshop options from which to choose, and the annual presentation of “A Christmas Carol” is a perennial favourite. more
Talent Machine Company, The 410-956-0512
P.O.Box 6418
Annapolis, MD 21401
This company produces three musicals each year and takes it as a mission to encourage young people to learn about the performing arts and take part in presenting high quality productions to the public. more

Art Exhibits

Annapolis Art Walk 410-267-7077
215 Main Street
Annapolis, MD 21401
This annual event allows one to take an artistic walk through Annapolis and visit over twenty art galleries, learn about different schools and styles of art, and watch over the shoulders of artists engaged in the creative process of creating art itself. more

Arts & Crafts Shows

Anne Arundel Country Fair Spring Craft Show 410-923-3400
1450 Generals Highway
Annapolis, MD 21032
Held at the Anne Arundel County Fairgrounds
This annual two-day event is held in late April and features over one hundred craftsmen, a variety of food and delicacies, and open admission and parking. more
First Sunday Arts Festival 410-741-3267
79 West Street
Annapolis, MD 21401
Calvert Street and West Street
Watch the streets in downtown Annapolis transform into an open air market. Enjoy arts, crafts, live entertainment and street-side cafe dining in an outdoor arts festival setting. This event takes place on the first Sunday of each month May through October and features Annapolis' finest artists and musicians. This event is fun, free, and family friendly. Each festival runs from 12 to 5 p.m. - weather permitting. more

Festivals & Fairs

Maryland Renaissance Festival 410-266-7304
Crownsville Road
Annapolis, MD 21032
Located in Crownsville in Anne Arundel County
Every weekend from the end of August to mid-October, enjoy an outdoor English Tudor village at the "second largest Renaissance Festival in the country." Step back to the times of the Renaissance and learn about the costumes, customs, foods, and arts and crafts of this time period. Witness dances and such spectacles as knights engaged in the ancient contest of jousting on horseback. more
Maryland Seafood Festival 410-353-9237
Sandy Point State Park
A variety of seafood, chef demonstrations, competitions, live musical entertainment, kids' activities, exhibits, contests, arts & crafts, and more can be enjoyed by the whole family on the shores of the Chesapeake Bay during the annual Maryland Seafood Festival, held each September. more

Sporting Events

Bay Bridge Boat Show 410-268-8828
Bay Bridge Marina, P.O. Box 4997
Annapolis, MD 21403
Kent Island
Usually held in late April, this annual and popular, premier boat show features new and used power boats and sailboats, as well as new boating equipment, accessories, services, and more. more
Naval Academy Athletic Association 410-268-6220
566 Brownson Road
Annapolis, MD 21402
Here one can enjoy Navy football, other sports, the majestic pageantry of the Brigade of Midshipman march, fly bys, parachuting Navy Seals, and much more. more

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