• The Best Christmas Pageant Ever

    The Best Christmas Pageant Ever
    The Colonial Players, 108 East St, Annapolis, MD 21401, USA

    This beloved holiday tale brings the notorious Herdman kids crashing into the church Christmas pageant. Chaos turns into comedy and a little holiday magic. What starts as a disaster blossoms …

  • A Christmas Carol

    A Christmas Carol
    Classic Theatre of Maryland 1804 West Street, Suite 200, Annapolis, United States

    For years, A Christmas Carol has been the heart of Classic Theatre of Maryland's annual holiday celebration, welcoming generations of families to experience Charles Dickens' timeless story of hope, redemption, …

    $61.75 – $98.75
  • Holiday Sip & Shop at Wine Cellars and Grapes Wine Bar

    Wine Cellars of Annapolis 1410 Forest Dr, Annapolis, United States +1 more

    Holiday Sip & Shop at Wine Cellars of Annapolis and Grapes Wine Bar Join us for a fun evening sipping wine and shopping from local artisans and crafters Friday, December …

  • 1776: Yuletide in Revolutionary Annapolis

    Hogshead Trades Museum 43 Pinkney St, Annapolis, United States +1 more

    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 …

    Free – $15
  • The Nutcracker (Mini Show)

    The Nutcracker
    Maryland Hall 801 Chase Street, Annapolis, Maryland, United States

    Infused with historical detail and regional charm, BTM’s Nutcracker transports audiences to 19th-century Annapolis. From the exciting naval battle between the Nutcracker and the Rat King to delicate crabs and …

  • Annapolis’ Holiday Market

    Annapolis’ Holiday Market
    West Street, West St, Annapolis, MD 21401, USA +1 more

    Visit Annapolis' West Street this holiday season and enjoy a special outdoor Holiday Market on Thursday night, December 10 and 17 when the first block of West Street transforms into …