5 events worth checking out in Annapolis as we approach the holidays


Grand Illumination – City Tree Lighting

When: Sunday November 25 : 5:30-7:15pm

Where: Market Space at the Market House, 25 Market Street Annapolis, MD

Tell me more: The Annapolis Jaycees (Junior Chamber of Commerce), with the support of the Annapolis business community, will host the Lighting of the Tree in Annapolis during the city’s Grand Illumination event for another year running. During this event, Santa’s arrival surprises the crowd and many enjoy the singing and dance performances by area youth. The Jaycees contribute refreshments and ornaments children can use to decorate the tree. Viewers are encouraged to bring nonperishable food items and new, unwrapped toys for the Jaycees’ annual Angel Tree Project.


Chocolate Binge Festival

When: December 2nd

Where: First Block of West Street Downtown, Annapolis

Tell me more: Specialty restaurant candy events include a chocolate fountain, candy apples, candy floss, “chocolate sushi”, and more. Attendees can revel in live music, a marshmallow roast, an ugly sweater contest, as well as a moon bounce and other kids’ activities. The evening concludes with an illumination of the sky above the first block of West Street. This event is given by the Annapolis Arts District and Inner West Street Association.


Midnight Madness Holiday Shopping

When: December 6, 13, & 20th

Where: Downtown Annapolis

Tell me more: Historic Annapolis shops welcome all interested in a magical night of browsing, purchasing and gifting. Participants may walk the streets while enjoying musical performances as well as food and refreshments. The participating stores are along Main StreetState Circle/Maryland Avenue, and the Arts District. Presented by the Downtown Annapolis Partnership.

Parade of Lights Cruise

When: Saturday December 8th, 4:45- 8pm

Where: Begins and ends at the Severn Inn

Tell me more: If you are interested, dinner can be booked at the Severn Inn followed by a dessert cruise on the stately Catherine Marie to watch the decorated boats coasting along Spa Creek in the Eastport Yacht Club Lights Parade. Visit www.watermarkjourney.com for more information.


Military Bowl

When: Monday December 31st ; beginning at 12pm

Where: Navy- Marine Corps Memorial Stadium

Tell me more: The Military Bowl® presented by Northrop Grumman, benefiting the USO, will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC). Visit www.militarybowl.org for more information.

Tickets for events and more information can be found at www.visitannapolis.org

Other Winter/Holiday Annapolis Events:

State House by Candlelight

Illuminated London Town

Lights on the Bay

Holiday Candlelight Stroll

Jolly Express Cruise

Annual Eastport Yacht Club Lights Parade

City of Annapolis New Year’s Celebration