Events and Things to Do in Highland, MD

Saturday, October 10

Featured

Frederick Ski Swap

OCT

10

9:00 AM

Frederick Fairgrounds - Home of The Great Frederick Fair, 797 E Patrick St, Frederick, MD

SnowRiders get ready for winter fun!! A consignment sale of ski & snowboard equipment, brand name winter clothing, accessories,...

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Sunday, October 11

Featured

Harbor City Music Company Presents: The Show Must Go On!

OCT

11

3:00 PM

Jim Rouse Theatre for the Performing Arts, 5460 Trumpeter Rd, Columbia, MD

Harbor City Music Company presents “The Show Must Go On!” a bi-annual theatrical-inspired performance that transforms music,...

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Thursday, October 15

Featured

MURDER MYSTERY - Midnight Masquerade

OCT

15

5:45 PM

5430 Vantage Point Rd, Columbia, MD

Mystery and murder at Oakland Manor.  Join in on the fun to enjoy friends, family, appetizers and cocktails!  REGISTER TODAY! ...

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Friday, October 16

Featured

Howard Community College Presents Fall for All!

OCT

16

11:00 AM

Howard Community College, 10901 Little Patuxent Pkwy, Columbia, MD

It’s fall, y’all! Grab your family, round up your friends, and head to Howard Community College for Fall for All—a fun-filled...

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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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Saturday, October 10

• Frederick Ski Swap 9:00 am

  Frederick Fairgrounds - Home of The Great Frederick Fair, 797 E Patrick St, Frederick

  
  
• Beginner's Bird Walk at Schooley Mill Park

  8:00 am

  Schooley Mill Park, 12975 Hall Shop Road, Highland

  
  

Sunday, October 11

• Harbor City Music Company Presents: The Show Must Go On! 3:00 pm

  Jim Rouse Theatre for the Performing Arts, 5460 Trumpeter Rd, Columbia

  
  
• U.S. Marine Band Chamber Music Ensemble 4:00 pm

  St John's Episcopal Church, 9202 Frederick Rd, Ellicott City

  
  

Thursday, October 15

• MURDER MYSTERY - Midnight Masquerade 5:45 pm

  5430 Vantage Point Rd, Columbia

  
  

Friday, October 16

• Howard Community College Presents Fall for All! 11:00 am

  Howard Community College, 10901 Little Patuxent Pkwy, Columbia

  
  

Sunday, October 18

• Family Goat Yoga 10:00 am

  Strohmer's Farm, 3501 Hernwood Rd

  
  
• Howard Lions Pride Athletic Boosters 2026 Fall Arts, Crafts, & More Show 10:00 am

  Howard High School, 8700 Old Annapolis Rd, Ellicott City

  
  

Thursday, October 22

• Chesapeake Bay Blues Quilt Show 10:00 am

  First Presbyterian Church of Howard County (PCUSA), 9325 Presbyterian Cir, Columbia

  
  

Saturday, October 24

• Frightreads Book Festival 6 12:00 pm

  Howard County Fairgrounds

  
  

Saturday, November 7

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

  Adventist HealthCare Fieldhouse, 18031 Central Park Cir

  
  

Sunday, November 8

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

  Adventist HealthCare Fieldhouse, 18031 Central Park Cir

  
  

Friday, December 4

• Annapolis Holiday Market 11:00 am

  2040 Annapolis Mall Rd, Annapolis, MD, 21401