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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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☕️🌊 Looking for your next local coffee obsession? We may have found the perfect summer morning spot.

Nestled right on the water in Eastport, Oscar’s Coffee is serving up coastal vibes, incredible coffee, and some of the best waterfront views around. From the iced pistachio latte (a definite must-try) to seasonal favorites and refreshing summer sips, this charming little coffee trailer is quickly becoming a local favorite.

Whether you’re taking a morning walk, meeting a friend, or just looking for a peaceful spot to start your day, Oscar’s delivers the kind of laid-back Eastport experience that summer is all about.

✨ Read our full Local Food Finds feature on Oscar’s Coffee, linked in our bio and below!
annapolismomsmedia.com/oscars-coffee-brings-waterfront-charm-to-eastport/

#LocalFoodFinds #EastportMD #AnnapolisMoms #MarylandEats #CoffeeLovers SupportLocal SummerInAnnapolis
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BACKYARD BOBBY’S W

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