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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

November 3, 2025 by Piper Langenfeld

Week of 11/6-11/12

Presented by

Thursday, November 6

Share the Warmth at Annapolis Mall | Discoveries: Library at the Mall (Nov. 6-30)

Philadelphia’s Fairmount Park Historic Homes: Bus Tour with Historic Annapolis | Maryland Hall

Golden Gatherings are HERE. a pop-up shop | 6 Fleet Street, Annapolis (Nov. 6-9)

Dracula: A Comedy of Terrors | The Colonial Players (Nov. 6-9)

Friday, November 7 

Annapolis Jazz & Roots Festival | Annapolis (Nov. 7-9)

Santapolis: A Magical Holiday Experience | Annapolis Mall (Nov. 7-Dec. 24)

Veterans Classic: Navy Men’s Basketball vs Yale | United States Naval Academy: Alumni Hall 

Navy Men’s Ice Hockey vs TCNJ | Brigade Sports Complex (Nov. 7 & 8)

The Lion, the Witch, and the Wardrobe | Annapolis Area Christian School (Nov. 7 & 8)

West Side Story | Children’s Theatre of Annapolis (Nov. 7-9)

Annapolis Symphony Orchestra Presents Darkness to Light | Maryland Hall (Nov. 7 & 8)

The Diary of Anne Frank | Anne Arundel Community College (Nov. 7-9)

Saturday, November 8

A Native American Heritage Month Lecture & Hike | Jug Bay Wetlands Sanctuary 

Second Saturday Divorce Workshop | CovingtonAlsina: Virtual 

Annapolis Crystals Presents Programming a Master Crystal Through Shamanic Journey | 158 W Lake Drive, Annapolis 

Illuminate Annapolis | Anne Arundel Community College 

Comic & Music Fair | ArtFarm

Sip Happens: Fall Community Brunch | Twain’s Tavern 

Comedian Michael Kosta | Rams Head On Stage

Watermark Presents the Annapolis Sunset Cruise | Annapolis City Dock 

Watermark Presents the Weird, Wacky, & Unusual History of Annapolis Tour | 188 Main Street 

Painting Your Garden: Pumpkins | Homestead Gardens: Davidsonville

The Tug of War | Spa Creek Bridge

Sunday, November 9 

Bay Bridge Run | Chesapeake Bay Bridge 

Annapolis Crystals Presents Gathering of Light: An Akashic Records Circle | 158 W Lake Drive, Annapolis

Naptown Flea | Federal House 

Taste of Fall on West Street | 53 West Street, Annapolis

Monday, November 10 

Honoring the Legacy: Black Veterans from the Revolution to the Present | Banneker-Douglass-Tubman Museum: Virtual

1940s Cabaret: Stage Door Canteen | Classic Theatre of Maryland (Nov. 10 & 11)

Tuesday, November 11 

Deadgrass: Bluegrass Covers of The Grateful Dead | Live Arts Maryland Studio 

Homeschool STEAM: How Seeds Travel | Eastport-Annapolis Neck Library 

Rams Head Presents Colin Hay | St. John’s College 

Wednesday, November 12 

Kids’ Club Workshop: Fall Leaf Lantern Workshop | Homestead Gardens: Severna Park & Davidsonville Acoustic Alchemy | Rams Head On Stage

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Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

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Every September, new students and faculty arrive by boat for their first day at The Gunston School, stepping onto their docks to a shoreline lined with cheering peers, parents, and teachers. After stepping ashore, signing the Honor Code, and walking up the hill through a welcoming line of fist bumps and high fives, they officially become part of the Gunston family.

That deep sense of community and connection sets the foundation for everything they do—and they invite your family to experience it firsthand!

Join Them for a Fall Open House on Sunday, October 18. Tour their waterfront campus, meet students and faculty, explore their academic and leadership programs, and see how their vibrant community helps students thrive.

Click here to RSVP:
gunston.org/openhouse
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