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Do Not Miss List

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Week of 10/15-21

Thursday, October 15

Great Annapolis Pumpkins | Downtown Annapolis (Oct. 15-30)

Middle School Visit Day | Annapolis Area Christian School 

Annapolis Sailboat Show | Annapolis City Dock (Oct. 15-18)

ProMD Health’s 15th Birthday Party | ProMD Health: Various Locations

Aesthetic sale and a chance to win free Botox. 

Tractor Treat | Homestead Gardens: Davidsonville 

Farming-themed trick-or-treating.

Comedian Josh Blue | Rams Head on Stage 

Friday, October 16

Locally Gathered HERE. a pop-up shop | 110 Dock Street, Annapolis (Oct. 16-Nov. 8)

Colossal Cares Presents the #22FORYOU DAY | Navy-Marine Corps Memorial Stadium 

Supports veterans and their mental health. Contests, food, and inspiring stories.

Splash Club | Center Lane Swim School 

Water safety and playtime in the pool. 

Ballet Theatre of Maryland Presents La Sylphide | Maryland Hall (Oct. 16-18)

A classical ballet about a sylph, her human lover, and a witch with unknown intentions. 

Navy Women’s Soccer vs Bucknell | United States Naval Academy: Glenn Warner Soccer Facility 

Saturday, October 17

Elementary School Allowance Workshop | CovingtonAlsina

Annapolis Dragon Boat Club Presents DragonFest 2026 | Pier 4 Marina 

A family friendly festival that supports anyone impacted by breast cancer. Live music, food, and more.

Paws and Pumpkins Fall Fest | AmericanK9 Dog Ranch  

Bull & Oyster Roast | The Gunston School 

BBQ, oysters, cocktails. 21+.

Party in the ‘Port: Boat Show Edition | Eastport Yacht Club 

Sunday, October 18

Calm for a Cure | Even Keel Wellness Spa: All Locations 

Free care and wellness services for anyone impacted by cancer. 

Maryland Ave Fall Festival | Maryland Avenue, Annapolis 

Monday, October 19

Evan Honer | Rams Head on Stage 

Tuesday, October 20

Leadership Anne Arundel and Maryland Hall Present Ignite Annapolis | Maryland Hall 

Presentations by locals, five minutes each. 

Wednesday, October 21

Historic Annapolis Presents the Orlando Ridout V Memorial Lecture: Jobie Hill | Historic Inns of Annapolis

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About Ricky Hartford

Ricky Hartford is fueled by cold brew, Celtics highlights, pop culture, and a perfectly placed Oxford comma. By day, he works in marketing and communications at Anne Arundel Community College, where he helps shape the college’s voice through content and storytelling. With over a decade of experience and a Master of Science in Strategic Communications, he’s helped nonprofits and local publications sound sharper, look better, and connect more clearly with their audiences. When he’s not working, he’s probably at the movies, on the basketball court, planning his next vacation, or convincing someone (anyone) to talk about the latest trashy reality show. Annapolis is his happy place, especially if it involves a drink downtown and hanging out by the water.