Baby, it’s cold outside! Why not stay in and enjoy a show?! Annapolis has a vibrant performing arts scene that draws talent from our own community to Broadway. The holidays are one of the best times of year to enjoy theatre, concerts, dance and even nationally touring shows. Here we round up the best of what’s ahead for the festive season, including a few free finds! 

Annapolis Shakespeare Company: A Christmas Carol 

Multiple Dates through December 29

Join the ghosts of Christmas Past, Present, and Future as they lead the miserly Ebenezer Scrooge on a journey of transformation and redemption, designed for the whole family to celebrate and enjoy. This annual holiday tradition, updated for the 2019/20 season, captures the magic and joy of Dickens' Yuletide classic with Annapolis Shakespeare Company's signature flair.


Annapolis Shakespeare Company: A Broadway Holiday 

Multiple Dates through December 28

This original evening of music and dance includes Holiday favorites from the stage and silver screen. With live accompaniment and our popular Broadway performers, audiences enjoy a confection of toe-tapping musical numbers sure to delight young and old(er) alike especially since all the festivities are set as a live radio broadcast in 1946. Don't miss the chance to celebrate the Holidays Broadway-Style!


Colonial Players: The Best Christmas Pageant Ever 

December 5-15

In this hilarious holiday classic put on by the Colonial Players, a couple struggling to put on a church Christmas pageant is faced with casting the Herdman kids – probably the most inventively awful kids in history. You won't believe the mayhem – and the fun – when the Herdmans collide with the Christmas story head on! Based on the book by Barbara Robinson, this festive and funny tale is about the meaning of Christmas.

Holiday Performances

Annapolis Symphony Orchestra: Broadway Pops

 December 13

‘Tis the Season! Three of Broadway’s leading men join Music Director José-Luis Novo and the orchestra the greatest holiday songs to life. From holiday classics to new favorites, this concert is the perfect way to make your spirit bright! Musical selections include Sleigh Ride, Jingle Bell Rock, Santa Claus is Coming to Town, A Holly Jolly Sing-A-Long and much more!


United States Naval Academy Band: Holiday By the Bay

December 13

Celebrate the season with the Naval Academy Band! Their annual "Holiday by the Bay" concert will take place at the Main Chapel on the grounds of the United States Naval Academy. Under the direction of Lieutenant Commander Patrick K.Sweeten, USNA Band will feature multiple ensembles performing a variety of multicultural holiday favorites, from traditional to modern. Santa Claus will pay a special visit! Free and open to the public.


Ballet Theatre of Maryland: The Nutcracker

December 14 & 15

Experience the wonder of this timeless holiday tradition. Allow yourself to be magically swept away by the tale of the young heroine Clara and her adventures to rescue her beloved Nutcracker from the Rat Queen’s evil spell. Travel with Clara through the whirling Kingdoms of Snow and Sweets to the place where the possibility of dreams, the magic of Christmas, and the wonder of the child merge to reveal her destiny through the powerful language of dance and theater. 

Holiday Performances

Christmas Carols at United States Naval Academy Chapel

December 15

Led by Mr. Monte Maxwell, USNA's Chapel Organist and Director of Chapel Music, come usher in the Christmas Season in the beautiful Naval Academy Chapel. Bring a list of your favorite carols and get ready to sing your heart out! Free, no tickets required.

Holiday Performances

CeeLo Green Holiday Hits

December 16

Grammy Award winning singer, songwriter, and producer CeeLo Green brings his “Holiday Hits Tour” to Annapolis. CeeLo will be performing fan favorites from his critically acclaimed and Grammy Award-winning album, "CeeLo’s Magic Moment", including What Christmas Means to Me, This Christmas, All I Want and more. Rams Head Presents at Maryland Hall.


AMFM Presents An Annapolis Christmas at Rams Head On Stage

 December 17

Join us along with the Annapolis Musicians Fund for Musicians at this annual favorite! We’ve got a great lineup of talented local artists that will be performing a mix of original and classic holiday songs. This show was inspired by the release of the popular holiday album, "An Annapolis Christmas" 21 years ago, and is now an annual tradition for many local music lovers.


ENCORE Rocks Holiday Concert

December 21

Encore ROCKS Annapolis and the Anne Arundel Community College Encore Chorale will perform a free holiday concert at Maryland Hall. Perfect for all ages, enjoy holiday classics and seasonal favorites sure to get you in the holiday spirit, including Santa Claus is Coming to Town, Blue Velvet, Last Christmas, and Good Vibrations  Led by professional conductor Jeffrey Dokken, the singers are all aged 55 and up. Free, no tickets required.

Annapolis Chorale: Handel’s Messiah

December 20 & 21

The Annapolis Chorale's annual performances of "Messiah" have become a regional holiday tradition! World-class soloists, the Annapolis Chamber Orchestra and, of course, the Annapolis Chorale all come together in historic St. Anne's Church for a powerful presentation of this iconic work.