A Christmas tree lit up at night on a rainy streetfront.

Explore our signature holiday events, wander through our historic streets, and shop for everyone on your list at one of our charming shopping districts! There is so much to see and do when you plan your winter getaway to Annapolis & Anne Arundel County!

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There is a lot to see and do in our beautiful Chesapeake Bay region, the only question is, what are you looking to experience?

Where Adventure


Adventure comes in many forms... From the historic charm of Annapolis along the shores of the Chesapeake Bay to the entertainment district of BWI and Arundel Mills, discover all that Annapolis and Anne Arundel County have to offer. Plan your adventure today!

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Major Events

Eastport Yacht Club Lights Parade

The magical Eastport Yacht Club Lights Parade takes place along the Annapolis Harbor and Spa Creek on the second Saturday in December every year. This annual tradition has been delighting holiday revelers for 40 years!

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Military Bowl

The Military Bowl, presented by Peraton, benefiting USO of Metropolitan Washington-Baltimore, is a post-season National Collegiate Athletic Association-sanctioned Division I college football bowl game. The game has been played annually in...

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  • Visitors Center
  • Arts District
  • City Dock & Ego Alley
  • Eastport
  • Main Street
  • Maryland State House
  • Navy-Marine Corps Memorial Stadium
  • St. John's College
  • State Circle & Maryland Avenue
  • United States Naval Academy
View All Walkable Points of Interest
Chesapeake Bay Severn River Spa Creek Annapolis Eastport WestAnnapolis 50 70 450 450 450 450 United States Naval Academy Eastport City Dock& Ego Alley Arts District Main Street St. John's College State Circle & Maryland Avenue Navy-Marine Corps Memorial Stadium Visitors Center Maryland State House
  • Anne Arundel County Fairgrounds
  • Annapolis Harbour Center
  • Annapolis Town Center
  • Historic London Town & Gardens
  • Quiet Waters Park
  • Westfield Annapolis
View All Driveable Points of Interest
  • Live! Casino & Hotel
  • Arundel Mills Mall
  • BWI Airport
View All BWI Airport & Arundel Mills Points of Interest
  • Waugh Chapel
  • Bowie Baysox Stadium
  • Laurel Park
View All West County Points of Interest
  • Herrington Harbor
  • Galesville Historical Society
  • Chesapeake Beach Resort & Spa
View All South County Points of Interest


A Christmas Carol

Classic Theatre of Maryland Details

Annapolis Holiday Market

Downtown Annapolis Partnership Details

Anne Arundel County Farmers Market (Sundays)

Anne Arundel County Farmers' Market Details
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