Annapolis Holiday Events are Diverse, Affordable, and Community-Wide

The winter holidays represent family traditions, love, community, and gratefulness. Very appropriately, the holiday themed entertainment in and around Annapolis reflect these ideals. We catalog the best and brightest things to do this holiday season, starting as early as ! Take a peek at the community events, music, and musicals below and enhance your end-of-the-year activities.

Downtown Community Events

What better way to welcome the holiday season than with a community-wide illumination downtown? This year’s Grand Illumination takes place the first of December, a Sunday, at Market Space. The illumination begins around 5:30 p.m.

December 5 and 19 , mark another year of Midnight Madness in downtown Annapolis, Eastport, and West Annapolis. Businesses stay open later and many offer great deals and discounts on gifts. Nearly all of downtown shops participate in this event in their own way–visit each to learn more.

Tuesday, December 10, welcomes two of our favorite things: eco-friendliness and holiday cheer. Annapolis Green puts on Holiday Green Drinks at Metropolitan Kitchen & Lounge off West Street from 5:30-7:30 p.m. In the spirit of Christmas, pledge to do something good for others–the environment included! This event is free and all are invited. Visit Annapolis Green to learn more.

Lights are somehow an integral part of the holiday season, and when those lights come in the form of a parade, we know the holidays are truly here. Eastport Yacht Club puts on their annual Parade of Lights on December 14, from 6 to 8 p.m. Boats travel around the downtown harbor and around Spa Creek lit up with fancy floats and vivid colors. Enjoy this free event with the entire family. To learn more, head to EYC’s website.

Holiday Music Performances

Maryland Hall for the Creative Arts lights up around this time of year, full of sparkling entertainers and joyous music to match the occasion. Thursday, December 5, Annapolis local Rob Levit performs alongside other local musicians in a holiday show. Levit will perform classic holiday tunes and carols. Tickets cost $20 for the general public and $15 for Maryland Hall members. All–including children–are invited this show. The show begins at 7 p.m. This event and the others below (unless stated otherwise) take place at Maryland Hall. Learn more information at Maryland Hall for the Creative Arts.

Sunday, December 8, The Annapolis Opera teams up with Calvary Methodist Church to provide a spectacular opera. Calvary hosts this holiday opera at 3 p.m. Guests can expect to hear impressive vocals and powerful instrumentals. The price for this show is $45 for the general public. Students and Maryland Hall members receive a discount–$15 for students and $40 for members, respectively.

December 8 also gets a dose of sweet soul, blues, spiritual chants, and gospel hymns interwoven with African flair thanks to Sweet Honey in the Rock. This eclectic and powerful women group brings a special “Holydays” celebration to the Maryland Hall stage at 7 p.m. Enjoy this multifaceted show by Grammy winning performers. Tickets for this event cost $58 for the general public and $53 for Maryland Hall members.

The Annapolis Chorale hosts a holiday celebration on Friday, December 13, at Maryland Hall. J. Ernest Green, Jenny Oaks Baker, and Alex Sharpe join musical forces with the Chorale to present an explosive Christmas-themed performance. All are invited to celebrate the season with this event. Tickets for most will cost $48. Students receive a $15 ticket price. The entertainment begins at 8 p.m.

Annapolis Symphony Orchestra celebrates all seasons effortlessly, but does an exceptional Christmas performance. “Holiday Pops” is the title of this year’s show that is scheduled for Friday, December 10, at 8 p.m. Maestro Jose-Luis Novo will direct the show that features special guests Five By Design. The show will be anything but mundane–the upbeat tunes and thrilling instrumentals will excite. Tickets cost $43 for the general public and $13 for students.

The Annapolis Chorale continues to entertain on December 20, 21, and 22 for a show entitled “Messiah at St. Anne’s,” which takes place at the church downtown. Not only will guests be treated to the sounds of the orchestra, but special performers will also entertain at the show. Friday and Saturday’s performances begin at 8 p.m.; Sunday’s performance starts at 3 p.m. Tickets for this downtown event cost $40 for the public, $15 for students, and $35 for MHCA members. Visit Maryland Hall’s site linked above for more.

Rams Head provides their own holiday celebration at the beginning of December. December 3rd brings “Christmas with The Celts” to Rams Head, a show that originated in Ireland but is replicated in downtown Annapolis. The pop/instrumental/Celtic Christmas music will awaken your holiday spirit. The show begins at 8 p.m. and costs $35. The next day, Peter White, Mindi Abair, and Rick Braun perform a Christmas show at 6:30 and again at 9:30 p.m. Each performance shows off jazzy pop Christmas favorites and costs $49.50. Friday and Saturday, December 6 and 7, Carbon Leaf performs holiday shows. Friday, Carbon Leaf joins with Logan Brill at 8 p.m. Saturday, the first holiday show is good for all ages and begins at 3 p.m. Later, Carbon Leaf plays again with Brill at 8 p.m. All three shows cost $29.50 individually. December 8, Motown & More present their own holiday celebration at 7:30 p.m. for $25. December 16 and 17, local Annapolis artists collaborate for a Christmas performance that benefits the Annapolis Musicians Fund. Approximately seven artists perform each night at 7 p.m. Tickets cost $32.50. The final Christmas performance is a true show-stopper: “Burlesque a Pades,” a holiday-themed burlesque show. Dinner is also available with this show. The show begins at 8 p.m. and costs $22.50. For more on these musical events, head to Rams Head.

Rams Head and Maryland Hall present Michael Bolton’s holiday show on December 17, scheduled at Maryland Hall. Bolton will perform his own holiday hits, beginning at 8 p.m. Tickets range from $59.50-$79.50. Head to the Rams Head link above to reserve your tickets.

If you enjoy a more intimate holiday experience, try out the live holiday performances at 49 West Coffeehouse. On Saturday, December 14, Redd Brothers present their Christmas show that features jazzy holiday favorites. The cost is $20. The performance begins at 7 p.m. See 49 West’s site for additional information.

Holiday Musicals and Plays

The Nutcracker–either in play, musical, or ballet form–is one of those obligatory holiday performances. This year, Ballet Theatre of Maryland puts on a series of ballet performance spanning two weekends. The Nutcracker in ballet form is arguably the most beautiful representation of this classic story. Tap into your childlike curiosity with this show acted out in front of you! December 14, December 15, December 21, and December 22 are the dates for this can’t-miss performance. Saturdays, the performance begins at 7 p.m.; Sundays, the two shows begin at 1 and 4:30 p.m. Tickets for adults cost $34.50; tickets for 10-year-olds and below cost $15.50. MHCA members get a discount. This performance takes place at Maryland Hall. More info can be found at the Maryland Hall link at the top.