January 29, 2023
Annapolis, US 42 F

A Re-Cap of Annapolis Holiday Events!

The City of Annapolis wants residents and visitors to enjoy a festive season of events and activities across the City.  Here is a list of the major events happening in Annapolis this month!

Midnight Madness: Three Thursdays in December – December 1 and 8 (4 p.m. to 12 p.m.) and December 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 for 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, December 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: December 3 (11 a.m. to 8 p.m.) and on December 4 (11 a.m. to 5 p.m.). Corner of Annapolis Street and Gidding Avenue.

Chocolate Binge Festival: Sunday, December 4 (10 a.m. to 5 p.m.). The first block of West Street (road closure: First block of West Street begins at 7:30 a.m. on December 4 until the festival’s close).  Chocolate, chocolate, and more chocolate, plus holiday shopping, and family-friendly entertainment, all take place underneath the festive West Street holiday light canopy. $5 tickets are available here.

Downtown Holiday Market: Thursday, December 8 (4 to 10 p.m.); Friday, December 9 and Saturday, December 10 (11 a.m. to 9 p.m.); and on Sunday, December. 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, December 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, December 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: Sunday, December 11 (7:30 to 12:30 a.m.). The Naptown Half Marathon will include rolling road closures downtown. Taylor Ave. between Rowe Blvd. and King George St. will be closed from 7 a.m. until 9:30 a.m. Please follow the Annapolis Police’s direction.

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

Annapolis Santa Speedo Run: Saturday, December 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: Sunday, December 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: Wednesday, December 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 the Annapolis Police’s direction.

Getting Around


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-colored 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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