The City of Annapolis wants residents and visitors to enjoy a festive season of events and activities throughout the city. Here’s a list of the top events happening in Annapolis this month!
Midnight Madness: On three Thursdays in December – December 1 and 8 (4:00 p.m. to 12:00 p.m.) and December 15 (4:00 p.m. to 11:00 p.m.). More than 90 downtown shops and 80 restaurants, including Main Street, Maryland Avenue, State Circle, West Street and City Dock, will be open late for this Annapolis tradition. Snap a selfie in Snowflake Alley, listen to 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 (December 1 and 8). For more information, contact the organizers of Midnight Madness – Downtown Annapolis Partnership.
Holiday Open House at the Town Hall: Thursday, December 1 (from 4:00 p.m. to 6:00 p.m.). Town Hall Chambers at the Town Hall, 160 Duke of Gloucester. Join Mayor Gavin Buckley, City Council members, City staff and neighbors for refreshments and entertainment before heading off to Midnight Madness.
West Annapolis Holiday Market: December 3rd (11:00 a.m. to 8:00 p.m.) and December 4th (11:00 a.m. to 5:00 p.m.). Corner of Annapolis Street and Gidding Avenue.
Chocolate Binge Festival: Sunday, December 4 (from 10:00 a.m. to 5:00 p.m.). First block of West Street (road closure: First block of West Street will begin at 7:30 a.m. on December 4 until the festival closes). Chocolate, chocolate and more chocolate, holiday shopping and family entertainment all take place under the holiday lights at the West Street Festival. $5 tickets are available here.
Central Holiday Market: Thursday, December 8 (from 4:00 p.m. to 10:00 p.m.); Friday, December 9 and Saturday, December 10 (11:00 a.m. to 9:00 p.m.); and Sunday in December. 11 (from 11:00 a.m. to 5:00 p.m.). Dock Street 1. Road closure along Dock Street. Between the Harbourmaster’s office and Susan Campbell Park. Arts, crafts, food and handmade items. Details at www.annapolisholidaymarket.com
Eastport Yacht Club Parade of Lights: Saturday, December 10 (6:00 p.m. to 8:00 p.m.). With viewing locations in historic downtown Spa Creek and Eastport. Magic happens at Spa Creek as illuminated boats suddenly appear on a cold winter’s night. Details at eastportyc.org/lights-parade.
Annapolis Santa Corrika: Sunday, December 11 (from 15:15 to 19:30). Firefighters from Annapolis and Anne Arundel County will be driving through neighborhoods in vintage fire trucks (with Santa) to collect unwrapped toys for distribution. Get pickup directions and schedule at: annapolissantarun.com.
Naptown Half Marathon: Sunday, December 11 (from 7:30 to 12:30). The Naptown Half Marathon will close downtown roads. Taylor Ave. Between Rowe Blvd. and King George Street will be closed from 7:00 a.m. to 9:30 a.m. Please follow Annapolis Police direction.
SoFo Ho-Ho: The South Forest (SoFo) Business Alliance is hosting a toy drive. “SoFo HO-HO” runs until December 13th, with giveaways on December 17th. Check www.SoFoAnnapolis.com for drop-off locations.
Annapolis Santa Speedo Run: Saturday, December 17 (11:00 a.m.), starting at O’Brien’s Oyster Bar (113 Main Street). Spreading holiday cheer since 2006 with a toy drive and running 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 its annual lighting of the City Dock Menorah after a caravan that begins at the Safeway on Housley Road.
Military ball Tail and Parade: Wednesday, December 28 (from 10:00 to 11:30). Road closures: Dock Street to Main Street to West Street to Taylor Avenue to Navy-Marine Corps Memorial Stadium. Follow the direction of Annapolis Police.
Free on the street: The city of Annapolis will continue its holiday tradition by offering three-hour parking in 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 lots in the historic district have migrated to paid parking via the ParkMobile app. Residents with a parking permit are exempt from hourly payment and time limits.
Garage: Gott’s Garage is the closest parking lot to the city center. Reserve parking at AnnapolisParking.com. The State Garage (Calvert St. John’s Sts.) is free after 6pm on weekdays and every day on weekends. Whitmore Garage is a $4 flat rate after 4:00 p.m. Garages in the West Street corridor at Knighton (1a Colonial Ave.), Park Place (One Park Place) and Graduate Hotel (126 West St.) are serviced by free downtown magenta. colored shuttle that runs every 5 to 8 minutes. The Magenta shuttle will run late in Midnight Madness.
Alternative mobility options
Bird electric bikes and scooters: Download the Bird app to find the nearest electric bike or scooter.
Annapolis GO: Operated by VIA, Annapolis GO is the City’s on-demand, ride-sharing service. Hop-on and hop-off to most locations in the city for $2 for the first passenger and $1 for each additional passenger in your group.