• 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
  • Williamsburg-Style Wreath Making Workshop

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

    Williamsburg Medallion Workshop with Maria from Beaver Creek Cottage Garden Celebrate the season with a touch of classic Southern charm! In this hands-on workshop, Maria of Beaver Creek Cottage Garden […]

    $95
  • Pilates

    Pilates
    Susan Ina Academy of Performing Arts 801 Barkwood Ct. Unit A-C, Linthicum Heights, MD, United States

    All ages, all levels welcome in this mat pilates class as we work on strengthening, lengthening and flexibility.  Make some time for yourself and your body this fall!

    $15 – $55
  • S. Carey (of Bon Iver) Solo + Strings w/ Hrishikesh Hirway

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

    S. Carey is the moniker of Eau Claire, Wisconsin-based multi-instrumentalist, songwriter, and producer Sean Carey, commonly recognized as the drummer, backing vocalist, and second longest serving member of Bon Iver. […]

  • Jane Austin Tour – December

    Hammond Harwood House 19 Maryland Ave, Annapolis, MD, United States

    Participants enjoy a 60-minute guided tour of the house that compares the customs and social graces of the Loockerman family, who lived in the Hammond-Harwood House in the early 19th […]

    $12
  • Dance With Me

    Dance With Me
    Susan Ina Academy of Performing Arts 801 Barkwood Ct. Unit A-C, Linthicum Heights, MD, United States

    Join your little mover in class as they learn the foundations of dance through stretching, fun dance exercises and simple routines.  Enjoy all the fun with them safe and happy […]

    $45
  • Mickey Guyton & Friends Holiday Tour w/ Special Guest Denitia

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

    Mickey Guyton is a 4-time, Grammy-nominated artist and country music trailblazer. With her debut studio album, Remember Her Name, Mickey made history as the first Black female artist to earn […]

  • Sketch Night 2026

    Sketch Night 2026
    ArtFarm Annapolis 111 Chinquapin Round Rd., Suite 200, Maryland

    Teens and Adults Welcome! Live figure drawing meets killer playlist. A unique life drawing experience featuring models ranging from burlesque performers to professional life models, in both costume and nude. […]

    $25 – $325