Events and Things to Do in Annapolis, MD

Monday, October 19

Featured

Charm City Arts/Culture: 5-Day Countdown to 1-Year Anniv. of Baltimore-Edition MONOPOLY Launch

OCT

19

12:00 PM

Baltimore, MD

Charm City Arts/Culture: 5-Day Countdown to 1-Year Anniv. of Baltimore-Edition MONOPOLY Launch October 19, 2026 - The...

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Saturday, October 24

Featured

Frightreads Book Festival 6

OCT

24

12:00 PM

Glen Burnie, MD

We're back! We're shaking out the cobwebs and ready to deliver our SIXTH year of FRIGHTREADS! You NEED to be here! WHEN:...

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Featured

Pilates w/Sarita Allen: Former Alvin Ailey Dancer!

OCT

24

1:00 PM

Crofton, MD

Elevate your Pilates practice with Guest Instructor Sarita Allen! Join renowned Pilates educator, teacher, choreographer, and...

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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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Monday, October 19

• Charm City Arts/Culture: 5-Day Countdown to 1-Year Anniv. of Baltimore-Edition MONOPOLY Launch 12:00 pm

  Baltimore

  
  
• Annapolis Rotary Annual Golf Tournament 9:30 am

  The Golf Club at South River, 3451 Solomons Island Rd, Edgewater

  
  
• Social Security Workshop - Understanding the Ins and Outs of Social Security 6:00 pm

  Zoom

  
  

Tuesday, October 20

• CourtFit at SportFit 11:00 am

  100 White Marsh Pk Dr, Bowie

  
  
• Women, Wine, & Wisdom™ - Estate Planning 7:00 pm

  Rams Head Tavern, 33 West St, Annapolis

  
  

Friday, October 23

• Navy Women's Volleyball vs Holy Cross 6:00 pm

  Wesley Brown Fieldhouse, Annapolis

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

  Glenn Warner Soccer Facility, Naval Academy

  
  
• Bountiful Harvest 7:00 pm

  The Atreeum at Soaring Timbers, 610 N Bestgate Rd, Annapolis

  
  
• Third Annual Halloween Dance 7:00 pm

  4 Pointless Forest Trail, Annapolis

  
  
• CP presents The Legend of Sleepy Hollow 8:00 pm

  The Colonial Players, 108 East St, Annapolis

  
  

Saturday, October 24

• Frightreads Book Festival 6 12:00 pm

  Howard County Fairgrounds

  
  
• Pilates w/Sarita Allen: Former Alvin Ailey Dancer! 1:00 pm

  1166 MD-3, Suite 105, Gambrills, MD, 21054

  
  
• Wine Cellars of Annapolis 25th Anniversary Celebration 10:00 am

  1410 Forest Dr, Annapolis

  
  
• Navy Women's Volleyball vs Colgate 12:00 pm

  Wesley Brown Fieldhouse, Annapolis

  
  
• Navy versus North Texas Football Game 3:30 pm

  550 Taylor Ave, Annapolis

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

  Glenn Warner Soccer Facility, Naval Academy

  
  

Sunday, October 25

• CP Open Auditions for When the Hurlyburly's Done 2:00 pm

  Colonial Players, 2132 Renard Ct, Annapolis

  
  

Saturday, October 31

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

  Cecil Memorial Umc, 15 Parole St, Annapolis

  
  
• Community Vaccine Clinic 9:00 am

  Cecil Memorial, 15 Parole St, Annapolis

  
  
• Community Harvest Festival 2026 1:00 pm

  Cecil Memorial, 15 Parole St, Annapolis