• 1776: Yuletide in Revolutionary Annapolis

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

    Celebrate the Holiday Season Through the Spirit of America 250 with Historic Annapolis! As America commemorates its 250th anniversary, step back to the holiday season of 1776 and experience Yuletide […]

    $3. – $17.
  • Bay Winds Band Winter Concert 2026

    Bay Winds Band Winter Concert 2026
    Unity by the Bay 4 Pointless Forest Trail, Annapolis, MD, United States

    Join the Bay Winds Band for our 2026 Winter Concert Series "What's in a Word" "What's in a Word."  Half-and-half program. The non-holiday half explores works that capture one-word ideas.  […]

    $10
  • Transform Your Photos: Photo Editing & File Organizing Workshop

    AND Creative Gallery 1851 McGuckian Street, Suite B, Annapolis, MD, United States

    "I Took Some Pictures. Now What?" Whether you've just returned from an unforgettable trip, captured your kid's birthday celebration, or want to showcase the beauty of your garden, your camera […]

    $150
  • Annapolis Chocolate Binge Festival

    Inner West Street Annapolis, Maryland

    About This Event A festival celebrating chocolate! The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. On Sunday, December 6th […]

    $6 – $70
  • First Sunday Arts Festival

    First Sunday Arts Festival
    Annapolis, 60 West St, 60 West Street, Annapolia, Maryland

    First Sunday Arts Festivals - Where Community and Arts FuseA monthly (May to November) street festival on the first Sunday of the month featuring 130 local and regional artisans, live […]

    FREE
  • The Annapolis Holiday Market

    The Annapolis Holiday Market
    Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Annapolis Holiday Market http://www.annapolisholidaymarket.com 1040 Annapolis Mall Road, Annapolis, MD 21401 December 4-6 and December 11-13 Hours: Fri- Sat 11 am-9 pm, Sun 11 am - 7 pm Free admission […]

  • Elizabeth Cook (matinee)

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Elizabeth Cook is a Nashville-based singer songwriter from Wildwood, Florida. As a critically acclaimed live act and recording artist, The New York Times lauds her “a sharp and surprising country […]

  • Bay Winds Band Winter Concert 2026

    St. Martin's Lutheran Church 1120 Spa Road, Annapolis, MD, United States

    Join the Bay Winds Band for their 2026 Winter Concert Series "What's in a Word" "What's in a Word."  Half and half program.  Non-holiday explores works that capture one-word ideas.  […]

    Free
  • Mindi Abair: I Can’t Wait For Christmas

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Mindi Abair’s I Can’t Wait For Christmas Tour is bringing the spirit of the holidays to audiences across the U.S. for an exciting, heartfelt season of music—now in its third […]

  • Tab Benoit w/ Bonerama: Blues and Brass Winter Tour

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Tab Benoit is a 4x Grammy nominated singer, songwriter and guitarist who has built a remarkable 30+ year career on the foundation of his gritty and soulful Delta swamp blues, […]

  • Creative Movement for Young Dancers

    Creative Movement for Young Dancers
    Susan Ina Academy of Performing Arts 801 Barkwood Ct. Unit A-C, Linthicum Heights, MD, United States

    Through music, imagination, and play, children will explore movement while developing coordination, balance, rhythm, and listening skills. Dancers will enjoy creative games, obstacle courses, props, and simple dance activities that […]

    $12 – $45