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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

September 9, 2025 by Piper Langenfeld

Week of 9/11-9/17

Presented by

Thursday, September 11 – Sunday, September 14 | Anne Arundel County Fair | Anne Arundel County Fairgrounds 

Thursday, September 11 – Sunday, September 14 | Annapolis Songwriters Festival | Annapolis

Thursday, September 11 | Black & White Gala | The Atreeum at Soaring Timbers 

Friday, September 12 | Small Business Owner/Entrepreneur Support Group | Betty Center

Friday, September 12 | Dirty Heads with BALLYHOO! & Wheeland Brothers | Calvert Street Stage

Saturday, September 13 | Second Saturday Divorce Workshop | CovingtonAlsina: Virtual

Saturday, September 13 | An Introduction To Your Human Design | Annapolis Crystals 

Saturday, September 13 | Watermark’s Weird, Wacky, & Unusual History of Annapolis Tour | 188 Main Street

Saturday, September 13 | Naptown Pop Up Market | Annapolis Town Center

Saturday, September 13 | Kunta Kinte Heritage Festival | Navy-Marine Corps Memorial Stadium

Saturday, September 13 & Sunday, September 14 | MD Corn Maze | Gambrills Road 

Saturday, September 13 | Tunes Through Time: The Sounds of Early Annapolis | Hogshead Trades Museum

Saturday, September 13 | Hunger Action Month Food Drive Event | Himmel’s Landscape and Garden Center

Saturday, September 13 & Sunday, September 14 | Maryland Seafood Festival | Sandy Point State Park

Saturday, September 13 | Live Music from Alex Peters | O’Loughlin’s Restaurant

Saturday, September 13 | Watermark’s Songwriters on the Severn | Annapolis City Dock

Sunday, September 14 | Annapolis RUN for The Light House | Quiet Waters Park  

Sunday, September 14 | Mrs. Howard’s Coffee House | Hogshead Trades Museum

Sunday, September 14 | Annapolis Vintage Market | Vintage Vibe Finds

Monday, September 15 & Tuesday, September 16 | 1920s Cabaret: The Speakeasy | Classic Theatre of Maryland 

Monday, September 15 | Casey Abrams & Friends featuring Dylan Chambers and Hunter | Rams Head On Stage

Tuesday, September 16 | Women, Wine & Wisdom: Aging in Place | Federal House 

Wednesday, September 17 | FarmUnity Harvest Festival | Crofton Library

Wednesday, September 17 | The Constitution: Promises and Challenges | 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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🍕 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!

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Let's see those BOO-tiful decorations, Annapolis! 🎃👻

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