Anne Arundel County Fair 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., 410-923-3400

Christmas in Annapolis and Anne Arundel County 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. , 410-280-0445

Eastport Yacht Club Lights Parade 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. , 410-263-0415

First Night Annapolis 100 Cathedral Street, Annapolis, MD 21401, 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. , 410-268-8553

Fourth of July Celebration 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. , 410-263-1183

Annapolis Holiday Stroll 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. , 410-280-0445

Mid-Atlantic Wine Festival 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., 410-280-3306

Annapolis Chorale 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. , 410-263-1906

Annapolis Symphony Orchestra 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. , 410-263-0907

Ballet Theatre of Maryland 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.” , 410-263-8289

Maryland Hall for the Creative Arts 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. , 410-263-5544

Annapolis Opera 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., 401-267-8135

Annapolis - Songs of the Sea - Concert Series 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.", 410-263-7837

Annapolis Summer Garden Theatre,Inc 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. , 410-268-9212

Colonial Players, Inc. 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. , 410-268-7373

Chesapeake Arts Center 194 Hammonds Lane, Annapolis, MD 21225, Brooklyn Park, MD, This nine-hundred-four-seat facility presents the best in concerts, plays, productions, and other creative arts events, as well as classes in dance, music, drama, acting, visual arts, and other areas. , 410-636-6597

Talent Machine Company, The 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. , 410-956-0512

Annapolis Art Walk 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. , 410-267-7077

Anne Arundel Country Fair Spring Craft Show 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., 410-923-3400

Maryland Renaissance Festival 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., 410-266-7304, 800-296-7304

Bay Bridge Boat Show 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., 410-268-8828

Naval Academy Athletic Association 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., 410-268-6220