• Holiday Traditions Tour of the William Paca House

    William Paca House and Garden 186 Prince George Street, Annapolis, MD, United States

    Experience the joy of the holiday season with a festive tour of the William Paca House! Gather your family and friends and begin the holiday season amidst the charming decorations of our historic mansion. You’ll be guided through the home of a Signer of the Declaration of Independence by your knowledgeable docent on a one-hour […]

    $3 – $17
  • Greater Annapolis Ballet Presents : The Nutcracker 2025

    Pascal Center for the Performing Arts 101 College Parkway, Arnold, Maryland

    Experience the magic of the season with Greater Annapolis Ballet’s beloved annual production of The Nutcracker, a timeless holiday tradition for the whole family! ✨ Choose from four enchanting performances: Friday, December 12 at 7:30pm Saturday, December 13 at 12:00pm – Clara’s Dream (a special shortened performance, perfect for younger audiences) Saturday, December 13 at […]

    $35
  • The Nutcracker

    The Nutcracker

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Be a part of something new! This holiday season, experience the world premiere of Annapolis’s own Nutcracker with Ballet Theatre of Maryland. The familiar story takes on local significance through vibrant dancing, historic costumes, and festive sets. Beloved characters like Clara, her enigmatic Uncle Drosselmeier, and the brave Nutcracker Prince return with new depth as their stories […]

    $47 – $72
  • The Nutcracker at BTM

    The Nutcracker at BTM

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    The Nutcracker with all-new choreography by Artistic Director Nicole Kelsch November 23, 2025 at Coppermine Pantherplex December 13-21, 2025 at Maryland Hall An Annapolitan take on this beloved classic!​ Be a part of something new! This holiday season, experience the world premiere of Annapolis’s own Nutcracker with Ballet Theatre of Maryland.  The familiar story takes on local […]

    $41 – $75
  • The Talent Machine Co. Presents “A Merry Mix-Up” Holiday Spectacular!

    Indian Creek School 1130 Anne Chambers Way, Crownsville, MD, United States

    Don’t miss The Talent Machine Company’s annual Holiday Spectacular, Dec. 12 through 23! Evening and matinee performances available! This year’s show – A Merry Mix-Up – promises to be an exciting experience for kids of all ages, with all of your favorite holiday songs and dances, plus a special surprise! What could possibly get mixed […]

    $20.00
  • Celebration of Christmas

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Yes, we deck the halls. But we also flood them with sound. With snow-dusted harmonies and velvet brass, this Annapolis tradition is anything but ordinary. Think “White Christmas” meets “Sleigh Ride” — plus a full-throated sing-along led by Maestro J. Ernest Green. Additionally, purchases can be made at the door and start at 6:15 pm […]

    $50
  • Small Gems

    Small Gems at McBride Gallery

    McBride Gallery 215 Main Street, Annapolis, MD, United States

    ‘Tis the Season for tiny treasures! We are featuring an array of Small Gems pieces throughout December and into the New Year. We are also featuring new work by Victor Nizovstev. The McBride Gallery is brimming with holiday spirit, and the artists are excited to share what they have made.

    Free
  • Holiday Artisan Market at The Galleries at Quiet Waters

    The Galleries at Quiet Waters Park 600 Quiet Waters Park Road, Annapolis, Maryland

    The Galleries of Quiet Waters Park is proud to present its 14th annual show/sale, “Holiday Artisan Market, Artistic Gifts of the Season,” which runs fro November 19, 2025 to January 4, 2026. Ten artists will be displaying and selling their work:  Joanne Bast (textiles),  Val Bembenek (paper boxes), Chesapeake Woodworkers (wooden artworks), Firelight Glass (fused […]

    Free
  • “Gifts from the Arts” Art Show and Sale

    “Gifts from the Arts” Art Show and Sale

    Hitching Post 5078 Solomons Island Rd, Lothian, MD, United States

    The Muddy Creek Artist Guild is thrilled to announce our ever popular Holiday Art Show and Sale .... and it starts on Black Friday! We have extended the weekends this year to give you more time to shop and browse. And that's not all. We are popping up at a new, bigger location in the […]

  • DIY Wrapping Paper: Monoprinting Workshop

    ArtFarm Annapolis 111 Chinquapin Round Rd., Suite 200, Maryland

    Mono Printing Magic: Create Your Own Wrapping Paper Join ArtFarm instructor Hailey Hagan for a fun, hands-on introduction to the colorful world of mono printing! Perfect for families and creative spirits of all ages, this workshop will teach you the exciting techniques of printing with Gelli plates. Discover how to design and create your own […]

    $65
  • Greater Annapolis Ballet Presents : The Nutcracker 2025

    Pascal Center for the Performing Arts 101 College Parkway, Arnold, Maryland

    Experience the magic of the season with Greater Annapolis Ballet’s beloved annual production of The Nutcracker, a timeless holiday tradition for the whole family! ✨ Choose from four enchanting performances: Friday, December 12 at 7:30pm Saturday, December 13 at 12:00pm – Clara’s Dream (a special shortened performance, perfect for younger audiences) Saturday, December 13 at […]

    $35
  • Silver in the Golden Age of Annapolis at Hammond-Harwood House

    19 Maryland Avenue, Annapolis 19 Maryland Avenue, Annapolis, MD, United States

    The decade prior to the American Revolutionary War (1760s-1770s) is considered the “Golden Age of Annapolis” because the city was regarded as the “genteelest town in North America,” and was a distinguished center for commerce, cultural pursuits, social events, and Georgian architecture. Hammond-Harwood House, 19 Maryland Avenue, is recognizing this description of our fair city […]

  • The Nutcracker

    The Nutcracker

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Be a part of something new! This holiday season, experience the world premiere of Annapolis’s own Nutcracker with Ballet Theatre of Maryland. The familiar story takes on local significance through vibrant dancing, historic costumes, and festive sets. Beloved characters like Clara, her enigmatic Uncle Drosselmeier, and the brave Nutcracker Prince return with new depth as their stories […]

    $47 – $72
  • The Nutcracker at BTM

    The Nutcracker at BTM

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    The Nutcracker with all-new choreography by Artistic Director Nicole Kelsch November 23, 2025 at Coppermine Pantherplex December 13-21, 2025 at Maryland Hall An Annapolitan take on this beloved classic!​ Be a part of something new! This holiday season, experience the world premiere of Annapolis’s own Nutcracker with Ballet Theatre of Maryland.  The familiar story takes on local […]

    $41 – $75
  • The Talent Machine Co. Presents “A Merry Mix-Up” Holiday Spectacular!

    Indian Creek School 1130 Anne Chambers Way, Crownsville, MD, United States

    Don’t miss The Talent Machine Company’s annual Holiday Spectacular, Dec. 12 through 23! Evening and matinee performances available! This year’s show – A Merry Mix-Up – promises to be an exciting experience for kids of all ages, with all of your favorite holiday songs and dances, plus a special surprise! What could possibly get mixed […]

    $20.00
  • The Nutcracker

    The Nutcracker

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Be a part of something new! This holiday season, experience the world premiere of Annapolis’s own Nutcracker with Ballet Theatre of Maryland. The familiar story takes on local significance through vibrant dancing, historic costumes, and festive sets. Beloved characters like Clara, her enigmatic Uncle Drosselmeier, and the brave Nutcracker Prince return with new depth as their stories […]

    $47 – $72
  • The Nutcracker at BTM

    The Nutcracker at BTM

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    The Nutcracker with all-new choreography by Artistic Director Nicole Kelsch November 23, 2025 at Coppermine Pantherplex December 13-21, 2025 at Maryland Hall An Annapolitan take on this beloved classic!​ Be a part of something new! This holiday season, experience the world premiere of Annapolis’s own Nutcracker with Ballet Theatre of Maryland.  The familiar story takes on local […]

    $41 – $75
  • Songs of the Season by Naptown Philharmonic Orchestra Chorus

    Eastport United Methodist Church 926 Bay Ridge Ave, Annapolis, MD, United States

    Naptown Philharmonic Orchestra Chorus Presents Songs of the Season Sunday, December 14, 7 pm Eastport United Methodist Church 926 Bay Ridge Avenue, Annapolis The Naptown Philharmonic Orchestra (NPO) invites everyone to the debut concert of its chorus, just in time for the holidays. Songs of the Season will feature holiday favorites, and there will be […]

    Free – $12