Events and Things to Do in Annapolis, MD

Tuesday, October 27

Featured

City of Baltimore: John Legend's Dec 28th Link to Colts vs Giants '58 NFL Championship, Jay-Z SB LXI

OCT

27

11:00 AM

Baltimore, MD

City of Baltimore: John Legend's Dec 28th Link to Colts vs Giants '58 NFL Championship, Jay-Z SB LXIOctober 27, 2026 - The...

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Thursday, October 29

Featured

Real Estate Online Auction | Annapolis, MD

OCT

29

6:30 PM

721 Fairway Dr, Annapolis, MD

🏡 ONLINE AUCTION • 721 FAIRWAY DRIVE, ANNAPOLIS, MD 21409 Original list price: $585,000 Opening bid: $250,000 Auction ends...

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Saturday, November 7

Featured

DMV Chocolate and Coffee Festival ~ Maryland Edition

NOV

7

10:00 AM

Adventist HealthCare Fieldhouse, 18031 Central Park Cir, MD

Saturday November 7, 2026VIP Hour = 9am-10amGeneral Admission = 10am-5pmBringing together artisan chocolatiers, specialty...

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Tuesday, October 27

• City of Baltimore: John Legend's Dec 28th Link to Colts vs Giants '58 NFL Championship, Jay-Z SB LXI 11:00 am

  Baltimore

  
  

Wednesday, October 28

• FREE Tai Chi Class 10:30 am

  Severna Park Community Center, 623 Baltimore Annapolis Blvd, Severna Park

  
  

Thursday, October 29

• Real Estate Online Auction | Annapolis, MD 6:30 pm

  721 Fairway Dr, Annapolis

  
  

Saturday, October 31

• Community Vaccine Clinic 9:00 am

  Cecil Memorial, 15 Parole St, Annapolis

  
  
• Harvest Festival Sponsors, Donors and Volunteers Needed! 9:00 am

  Cecil Memorial Umc, 15 Parole St, Annapolis

  
  
• Tavern Talk: Inside Annapolis’s Revolutionary-Era Taverns 11:00 am

  Hogshead Trades Museum, Historic Annapolis, 43 Pinkney St, Annapolis

  
  
• Community Harvest Festival 2026 1:00 pm

  Cecil Memorial, 15 Parole St, Annapolis

  
  
• Trunk Or Treat 1:00 pm

  Cecil Memorial, 15 Parole St, Annapolis

  
  

Sunday, November 1

• Navy Classic - Wrestling 10:00 am

  Wesley Brown Fieldhouse, Annapolis

  
  
• Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis 11:30 am

  Museum of Historic Annapolis, 99 Main St, Annapolis

  
  

Tuesday, November 3

• Navy Men’s Soccer vs American University 7:00 pm

  Glenn Warner Soccer Facility, Naval Academy

  
  

Wednesday, November 4

• Navy Women’s Soccer vs Loyola 8:00 pm

  Glenn Warner Soccer Facility, Naval Academy

  
  

Thursday, November 5

• Visit Brandywine Museum of Art and N.C. Wyeth House & Studio – A Bus Tour with Historic Annapolis 7:30 am

  Historic Annapolis

  
  
• Green Drinks Annapolis ~ Post-Election Edition 5:00 pm

  Graduate by Hilton Annapolis, 126 West St, Annapolis

  
  
• Men's Basketball vs Delaware State 7:00 pm

  Decatur Avenue, Decatur Ave, Annapolis

  
  

Friday, November 6

• Navy Women's Volleyball vs American 6:00 pm

  Wesley Brown Fieldhouse, Annapolis

  
  

Saturday, November 7

• DMV Chocolate and Coffee Festival ~ Maryland Edition 10:00 am

  Adventist HealthCare Fieldhouse, 18031 Central Park Cir

  
  
• Baltimore Ski Swap, 9am-2pm 9:00 am

  Roland Park Community Center, 5802 Roland Ave, Baltimore

  
  
• Navy versus Temple Football Game 3:30 pm

  550 Taylor Ave, Annapolis

  
  

Sunday, November 8

• DMV Chocolate and Coffee Festival ~ Maryland Edition 10:00 am

  Adventist HealthCare Fieldhouse, 18031 Central Park Cir