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Festive Annapolis Holiday Hotel Events

Celebrate the season with heartwarming attractions that are fun for the whole family. Let the kids take their photos with Santa, participate in a dockside candlelight stroll, and don't miss the popular Eastport Yacht Club Lights Parade. Sign up for a tour of the city, savor delectable dining, and enjoy exciting Annapolis holiday hotel events.

Upcoming Holiday Events

  • Annapolis by Candlelight
    November 4 - 5
    5:00 -9:00 pm
    Historic Annapolis
 
  • First Sunday Arts Festival - Holiday Edition 
    November 6
    12:00 -5:00 pm
    Sandy Point State Park
 
  • Lights on the Bay
    November 21 - January 2, 2016
    5:00 -10:00 pm
    Sandy Point State Park
 
  • Small Business Saturday
    November 26
    Begins 10:00 am
    Stores in Downtown Annapolis, Annapolis & Chesapeake Bay Region

  
  • Annapolis Christmas Tree Lighting
    November 27
    5:30 pm - 8pm 
    City Dock
 
  • Midnight Madness
    December 1, 8, 15
    6:00 pm - 12:00 am
    Downtown Annapolis
 
  • Chocolate Binge Festival
    TBA
    TBA
    First Block of West Street
 
  • Holiday Candlelight Stroll
    December 2-3, 9, 16-17
    7:00 pm - 8:30 pm
    City Dock
 
 
 
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  • Jolly Express Cruise
    Weekends in December
    7:00 pm and 8:00 pm
    City Dock
 
  • Parade of Lights Cruise
    December 10
    4:45 pm and 8:00 pm
    Severn Inn
 
  • Eastport Yacht Club Lights Parade
    December 10
    6:00 pm - 8:00 pm
    Annapolis Harbor and Spa Creek
   
  • 11th Hour Shopping Event
    December 15
    6:00 pm - 11:00 pm
    Downtown Annapolis
 
  • Annapolis New Year's Eve
    December 31
    3:00 pm - 12:00 am
    Downtown Annapolis
 
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