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Annapolis Holiday Lineup: Saturday Spooky Drive-In; Midnight Madness dates; No 12/31 fireworks

Updated: Jan 14, 2021

City Announces 2020 Holiday Schedule of Events

ANNAPOLIS, MD (October 27, 2020) – The cit's Halloween Drive_in is now on Halloween (Saturday, October 31) Annapolis Recreation and Parks is hosting the Halloween Drive-In Movie--Disney's "Hocus Pocus!"

There is a maximum allowed for this event so sign up soon!

Attendees are encouraged to decorate their vehicles – the best one will receive a prize!

Every child attendee will receive a premade goody bag and pre-packaged popcorn bag (staff will drop off bags to each car wearing masks and gloves prior to the movie starting).

All families must remain in their own vehicle space (no seats or sitting in the parking lot.)

Truck beds may be used as sitting space, but families must remain inside of them.

Outside bathrooms will be available (staff will clean after each use.)

Cost:is $10 per car; Attendees MUST BE pre-registered (no on-site registration)

Register with code #1929 online (existing customers) or in-person at Pip Moyer Recreation Center.

For more information, email or


The City of Annapolis also announced partnerships and schedules for the 2020 holiday season. All visitors, residents, and business owners are asked to be responsible for their own behavior and COVID-19 protocols to slow the spread of  coronavirus: wear a mask; practice physical distancing and wash hands or use hand sanitizer frequently. 

Parking: From Thanksgiving until January 2, 2021, parking in downtown Annapolis will include two hours free at metered spaces. Users of the ParkMobile app will get an additional hour free by using the PARKDTA.  There will be a flat $5 flat rate available in the Knighton and Gotts Garages for those who PREPAY via

Holiday Shopping and Decorations: The Annapolis Jaycees will receive a grant from the City for $17,000 to decorate storefronts in downtown and Eastport with greens and garland during the last weeks of November. 

The Downtown Annapolis partnership will also be chipping in from CARES Act funding and City grants to decorate City streets with holiday themed flags and banners, a Christmas Tree at Market Space, a Menorah at City Dock and decorative street lighting throughout downtown.

Snowflake Alley will be lit and decorated for socially-distanced selfies and romantic strolling. 

There will be three “Midnight Madness” events, with restaurants and retail stores in the downtown area open late. Both Main Street and Maryland Avenue will be closed to vehicles to allow patrons more space to socially distance. This space will also be used for tents for outdoor dining and some outdoor retail.

Shopping hours will also start two hours earlier this year at 4 p.m.  During Midnight Madness, the City is permitting businesses in the City’s Recovery Zones to continue expanded outdoor operations until midnight.   

The dates of Midnight Madness 2020 are: 

  • December 3 until midnight

  • December 10 until midnight 

  • December 17 until the Eleventh Hour (11pm).


Additional Free Parking for Midnight Madness:

  • Knighton Parking Garage: Free parking 4 p.m. to midnight during Midnight Madness

  • Gotts Court Parking Garage: Free parking Thursday to Sunday 4 p.m. to Midnight now through the winter

  • Hillman Parking Garage: Free parking Thursday and Friday 4 p.m. to midnight, Saturday noon to midnight and Sunday 10 a.m. to midnight now through the winter.


The Eastport Yacht Club will hold their annual Lights Parade, visible from City Dock and Eastport on December 12.

Chabad of Anne Arundel County will have a Menorah Lighting for Hanukkah at 5:45 p.m. on Sunday, December 13 on City Dock.   

New Year’s Eve: The City-sponsored tent party and fireworks festivities have been canceled this year due to the pandemic.

City Offices will be closed on November 26, 2020 for Thanksgiving; December 25, 2020 for Christmas and January 1, 2021 for New Year’s. 

--From Annapolis press releases