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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

October 7, 2025 by Piper Langenfeld

Week of 10/9-10/14

Presented by

Thursday, October 9

Bring a Friend Week with Chesapeake Youth Symphony Orchestra | Maryland Hall

Annapolis Sailboat Show | Annapolis City Dock (Oct. 9-12)

Watermark’s and Historic Annapolis’ Special Historic Hauntings | 188 Main Street (Oct. 9-11)

Crystal Sale | Annapolis Crystals’ Instagram Live 

Friday, October 10 

iDance4aCure | Creative Force Dance Center

Field Work Fridays | Jug Bay Wetlands Sanctuary 

Social Bridge | Captain Avery Museum 

A New World | Maryland Hall (Oct. 10 & 11)

Kristen DeBruycker Jiu-Jitsu Classes | Kogen Severna Park 

Saturday, October 11

Art @ the Park | Quiet Waters Park (Oct. 11 & 12)

Bird Watching 101: Heading South for the Winter | Historic London Town & Gardens

The Climb with Postpartum Support International | Annapolis Mall

Second Saturday Divorce Workshop | CovingtonAlsina: Virtual

Fall Fun Day | Kinder Farm Park 

Storytime at Hogshead: Tales of a Tradesperson | Hogshead Trades Museum

Naptown Vinyl Record Show & Vintage Market | Maryland Hall

Sacred Spaces Artist Talk | Banneker-Douglass-Tubman Museum 

Party in the ‘Port | Eastport Yacht Club

Watermark’s Weird, Wacky, & Unusual History of Annapolis Tour | 188 Main Street

Close Enemies featuring Tom Hamilton of Aerosmith | Rams Head On Stage

Sunday, October 12

Chestertown Challenge Half Marathon Run & 5K Run/Walk | Wilmer Park

Fall Harvest Festival + War of 1812 | Historic Hancock’s Resolution 

Cantori Presents: Wildflowers | Maryland Hall

A Conversation with Abby Phillip | Maryland Hall

Steven Page (Formerly of Barenaked Ladies) | Rams Head On Stage

Monday, October 13 

Social Security Webinar | CovingtonAlsina: Virtual 

Tuesday, October 14 

Birds of a Feather | Historic London Town & Gardens

National Dessert Day | Federal House 

Northern Slavery in Colonial America | Historic Annapolis: Virtual 

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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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Annapolis is going GREEN and we’ve got your full St. Patrick’s guide ready. 🍀✨

From the St. Patrick’s Day Parade (March 8!) to Shamrock the Lot, live Irish music, dance performances, pub parties, family storytimes, trivia nights, and so much more, there’s something happening all month long.

Whether you’re celebrating with the kids, meeting friends for a pint, or making a full day of it downtown, we rounded up everything you need in one place.

Grab your green, plan your crew, and start mapping out your month. 🍻
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