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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

About Piper Langenfeld

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Next Post:Eye on Annapolis: Top 5 in the News | October 6th, 2025 |

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🍕 TONIGHT’S DINNER? TAKEOUT, OF COURSE!

Too tired to cook? Too busy to meal prep? Annapolis has plenty of local spots where you can pick up dinner and bring it home to the family.

From pizza and tacos to family-friendly meals everyone can agree on, we rounded up local takeout options to make those busy weeknight dinners a little easier.

Because sometimes, getting dinner to go is the plan. 🙌

👉 Find your next family takeout spot here: annapolismomsmedia.com/dinners-covered-easy-family-takeout-meals-in-annapolis/

#AnnapolisMoms #LocalFoodFinds #AnnapolisEats #FamilyTakeout #DinnerToGo

The Lodge Annapolis Vivi's Chicken 'n Mac True Food Kitchen Red Hot & Blue Annapolis Whole Foods Market Ledo Pizza Cracker Barrel
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GIVEAWAY ALERT!!!

🎃 SHOW US YOUR SPOOKY SIDE! 👻

Have you decked out your porch with pumpkins, skeletons and spooky surprises? We want to see it!

Annapolis Moms is hosting an Outdoor Halloween Decorating Contest, and you could win a $100 Rams Head gift card, courtesy of Annapolis Moms community supporter Rams Head!

How to enter:

1. Snap a photo of your outdoor Halloween decorations.
2. Comment below and share your photos in the comments!

Make sure your house number or street address is NOT visible in your photo.

We'll select a winner and announce it in our Monday , November 2nd newsletter! So make sure you are subscribed!

Not subscribed? Sign up so you don't miss the big reveal:
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Let's see those BOO-tiful decorations, Annapolis! 🎃👻

#RamsHeadonstage #GreenstreetGardens #HomesteadGardens #AnnapolisHalloween
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