Upcoming Winter Holiday Events In Annapolis

ANNAPOLIS, Md. – The City of Annapolis invites residents and visitors to enjoy a festive season of events and activities across the City.  Please note: there will be road closures for some downtown activities including West Street this Sunday (Dec. 4) for the Chocolate Binge Festival and Francis Street during the first two (of three) Thursdays (Dec. 1 and 8) for Midnight Madness. Details of events and closures below: 

Midnight Madness: Three Thursdays in December – Dec. 1 and 8 (4 p.m. to 12 p.m.), and Dec. 15 (4 to 11 p.m.). More than 90 stores and 80 restaurants in the downtown area, including Main Street, Maryland Avenue, State Circle, West Street, and City Dock will be open late for this Annapolis tradition. Get a selfie in Snowflake Alley, hear carolers, visit the alpacas on Main Street and enjoy hot cocoa along the way. Francis Street from Main Street to State Circle will be closed the first two Thursdays (Dec. 1 and 8). For more information, contact the organizers of Midnight Madness – Downtown Annapolis Partnership

Holiday Open House at City Hall:  Thursday, Dec. 1 (4 to 6 p.m.). City Council Chambers at City Hall, 160 Duke of Gloucester. Join Mayor Gavin Buckley, City Council members, City staff and neighbors for refreshments and entertainment before heading out to Midnight Madness. 

West Annapolis Holiday Market: Dec. 3 (11 a.m. to 8 p.m.) and on Dec. 4 (11 a.m. to 5 p.m.). Corner of Annapolis Street and Gidding Avenue. 

Chocolate Binge Festival: Sun., Dec. 4 (10 a.m. to 5 p.m.). First block of West Street (road closure: First block of West Street beginning at 7:30 a.m. on Dec. 4 until the close of the festival).  Chocolate, chocolate and more chocolate, plus holiday shopping, family-friendly entertainment, all taking place underneath the festive West Street holiday light canopy. $5 tickets available HERE.

Downtown Holiday Market: Thurs., Dec. 8 (4 to 10 p.m.); Fri., Dec. 9 and Sat., Dec. 10 (11 a.m. to 9 p.m.); and on Sun., Dec. 11 (11 a.m. to 5 p.m.). 1 Dock Street. Road closures along Dock Street. Between the Harbormaster’s office and Susan Campbell Park. Arts, crafts, food and handmade items. Details at www.annapolisholidaymarket.com

Eastport Yacht Club Lights Parade: Saturday, Dec. 10 (6 to 8 p.m.). Spa Creek with viewing locations in historic downtown and Eastport. Magic happens on Spa Creek as lighted boats suddenly appear on a cold winter night. Details at eastportyc.org/lights-parade.

Annapolis Santa Run: Sunday, Dec. 11 (3:15 to 7:30 p.m.). Annapolis and Anne Arundel County firefighters will ride through neighborhoods on antique fire trucks (with Santa) to collect unwrapped toys for distribution. Get the pickup routes and schedule at: annapolissantarun.com.

Naptown Half Marathon: Sun., Dec. 11 (7:30 to 12:30 a.m.). The Naptown Half Marathon will include rolling road closures in downtown. Taylor Ave. between Rowe Blvd. and King George St. will be closed from 7 a.m. until 9:30 a.m. follow Annapolis Police direction. 

SoFo Ho-Ho: The South Forest (SoFo) Business Alliance is hosting a toy drive. The “SoFo HO-HO” will run though Dec. 13 with the distribution of gifts on Dec. 17. Check www.SoFoAnnapolis.com for drop-off locations. 

Downtown Speedo Run: Sat., Dec. 17 (11 a.m.), starting at O’Brien’s Oyster Bar (113 Main Street). Spreading holiday cheer since 2006 with a toy drive and a run through downtown Annapolis in a Speedo. Details: Santa Speedo Run

City Dock Menorah Lighting: Sun., Dec. 18 (5:30 p.m.). Chabad of Anne Arundel County will host the annual lighting of the City Dock Menorah after a caravan that begins at the Safeway on Housley Road.   

Military Bowl Tailgate and Parade: Wed., Dec. 28 (10 a.m. to 11:30 a.m.). Rolling road closures: Dock Street to Main Street to West Street to Taylor Avenue to Navy Marine Corps Memorial Stadium. Follow Annapolis Police direction. 

Getting Around

Parking

  • Free on-street: The City of Annapolis will continue the holiday tradition of offering three hours of free parking at metered spaces between Thanksgiving and New Year’s Day. The three-hour limit is enforced, so if you need a longer stay, consider migrating to a garage.
  • Residential parking in the historic district has migrated to paid parking through the ParkMobile app. Residents with a parking permit are exempted from hourly payments and time limits. 
  • Garage parking: Gott’s Garage is the closest parking to downtown. Reserve parking at AnnapolisParking.com. The State Garage (Calvert at St. John’s Sts.) is free after 6 p.m. on weekdays and all days on weekends. Whitmore Garage is a flat rate of $4 after 4 p.m. Knighton (1a Colonial Ave.), Park Place (One Park Place), and Graduate Hotel (126 West St.) garages along the West Street corridor are served by the free downtown magenta shuttle, which runs every 5 to 8 minutes. The magenta shuttle will operate late during Midnight Madness. 

Alternative Mobility Options

  • Bird e-bikes and scooters: Download the Bird app to find the nearest available e-bike or scooter.  
  • Annapolis GO: Operated by VIA, Annapolis GO is the City’s on-demand, shared-ride service.  Get to and from most locations in the City for $2 for the first passenger and $1 for each additional passenger in your group. 

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