Small Business Saturday and Grand Illumination Kick Start Holiday Season in Annapolis

City of Annapolis Offices Closed for Thanksgiving and Black Friday

ANNAPOLIS, MD - The City of Annapolis will close City offices on Thursday, November 27 and Friday, November 28 for the Thanksgiving holiday. 

  • Annapolis Transit: On Thanksgiving Day, November 27, Annapolis Transit will not operate. On Friday, transit services will operate on a normal schedule. 
  • Refuse and Recycling: Thursday collections will be moved to Friday; Friday collections will take place on Saturday. 
  • Annapolis Recreation and Parks: the Roger “Pip” Moyer Recreation Center and Stanton Community Center will both be closed on Thanksgiving Day (Thursday). The Stanton Center will be closed on Friday while the Pip Moyer Recreation Center will reopen at 6 a.m. on Friday.

“Each holiday season in Annapolis feels special and the winter holidays especially sparkle: the twinkling lights downtown, the scores of holiday events and festivals, and an overall sense of togetherness fills our city,” said Annapolis Mayor Gavin Buckley. “This is my last holiday season as Mayor of our wonderful capital city, and I am especially grateful for the spirit of community that defines Annapolis. Let’s celebrate what makes this city so extraordinary and carry that spirit with us into the new year.”

Additional Annapolis and community holiday updates:

Free Parking in Downtown: The City of Annapolis will continue the annual tradition of offering two hours of free parking at metered spaces between Thanksgiving and New Year's. To get two free hours, customers must use ParkMobile (web or app). The City is again offering the first hour free at the downtown Hillman Garage. More details on holiday parking.  

Annapolis Holiday events:

  • 19th Annual Annapolis Turkey Trot will take place on sidewalks around the Historic District at 9 a.m. on Thursday, November 27.
  • Watermark’s Jolly Express Cruises depart from the end of Prince George Street multiple days a week now through New Year's Eve.
  • Classic Theatre of Maryland will perform White Christmas from November 28 to December 28.
  • Small Business Saturday will take place at local shopping districts on Saturday, November 29.
  • The Downtown Annapolis Partnership will host the "Grand Illumination" tree lighting ceremony at Market Space from 3 to 5:15 pm. on Sunday, November 30.
  • Colonial Players performs a Christmas Carol December 3-14
  • The United States Naval Academy Men’s Glee Club and Women’s Glee Club will perform Handel’s Messiah on December 6-7 at the USNA Chapel
  • Live Arts MD will perform Handel’s Messiah at St Anne’s Episcopal Church from December 13 to 15
  • The Chocolate Binge Festival is from 11 a.m. to 5 p.m. on Sunday, December 7, with the first block of West Street closed to traffic.
  • Midnight Madness is back with retail stores staying open late on Dec. 4, 11 and 18 in downtown. The first block of West Street will be closed to traffic on December 11 and 18 and Maryland Avenue between Prince George Street to Cumberland Court will be closed to traffic. For more information, contact Downtown Annapolis Partnership, Inner West Street Association (www.iwsannapolis.com/), Maryland Avenue and State Circle Association (www.mascma.com).
  • The Mayor and Annapolis City Council will host an Open House in Annapolis City Council Chambers on from 4:30 to 6 p.m. on Thursday, December 4.
  • The West Annapolis Holiday Market will take place from 11 a.m. to 5 p.m. on Saturday, December 6. 
  • The Annapolis Holiday Market will take place on the campus of St. John’s College on Saturday, December 13 and Thursday to Sunday, Dec. 18-21. Hours vary.
  • The Eastport Yacht Club’s Lights Parade is scheduled from 6 to 8 p.m. on Saturday, Dec. 13. 
  • The downtown Santa Speedo Run is scheduled for Dec. 13 from O’Brien’s Oyster Bar & Seafood Tavern on Main Street. 
  • Chabad of Anne Arundel County’s lighting of the City Dock Menorah is set for December 14.
  • The Ballet Theatre of Maryland will perform The Nutcracker from December 13 to 21 at Maryland Hall. 
  • Annapolis Symphony Orchestra presents Holiday Pops on December 19 at Maryland Hall
  • Annual Kwanza Celebration is at the Banneker Douglas Tubman Museum on December 13 from 10 am to 4 pm
  • The Annapolis Fire Santa Run will take place in neighborhoods throughout Annapolis on Sunday, Dec. 14
  • The United States Naval Academy Brigade Christmas Carols will take place at the USNA Chapel on Dec. 14.  
  • The Naptown Half Marathon is set for the morning of Saturday, December 20 and will include rolling road closures in downtown.
  • City offices will be closed on Thursday, December 25. 
  • The Budweiser Clydesdales will parade on West Street during the Military Bowl Parade on Friday, December 26. The Miracle in Annapolis event will be at Maryland Hall following the parade. 
  • The Military Bowl will take place at Navy-Marine Corps Memorial Stadium on Saturday, December 27. 
  • The City will host New Year’s Eve fireworks over Spa Creek at 9 p.m. on Tuesday, December 31, 2025. 
  • City offices will be closed on Wednesday, January 1, 2026