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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

September 23, 2025 by Piper Langenfeld

Week of 9/25-10/1

Presented by

Thursday, September 25

Smithsonian SPARK! Places of Innovation Exhibit | Captain Avery Museum (September 25-October 5)

Blazers . Bourbon . Cigars | William Paca House & Garden

WAR: 50th Anniversary Tour of Why Can’t We Be Friends? | Rams Head On Stage (September 25-26)

FY27 Grant Application Training Series | Virtual

Women With Scars: Strength in the Storm | Betty Center

Friday, September 26

Social Bridge | Captain Avery Museum 

Ballet Storytime and Preview | Eastport-Annapolis Neck Library

The Galbani Maryland Italian Festival | Ripken Stadium (September 26-28)

Brigadoon | Maryland Hall (September 26-27)

Watermark’s Colonial Annapolis & Maryland State House Walking Tour + USNA Option | 188 Main Street (September 26-28)

Saturday, September 27 

Anne Arundel County Literacy Council Book Fair | Annapolis Mall 

The Crabtown Frolic | Downtown Annapolis (September 27-28)

Autumn Light Reiki, Sound Bath & Meditation | 158 West Lake Drive

AACS Fall Festival | Annapolis Area Christian School 

First Rhode Island Regiment with a Living Historian | Hogshead Trades Museum

Navy Football vs Rice | Navy-Marine Corps Memorial Stadium 

Live Music from Guava Jelly | O’Loughlin’s Restaurant

Watermark’s Annapolis Sunset Cruise with Sister Midnight Band | Annapolis City Dock

Freedom on the Horizon | Historic London Town & Gardens

Sunday, September 28

Spar A Thon | Kogen Dojo Annapolis

World Rivers Day | Historic London Town & Gardens

Anchors & Artisans | Annapolis Town Center

Oktoberfest | Annapolis Street

National Drink Beer Day | Federal House 

Kent Island Fall Picnic | The Kirwan House 

Monday, September 29

National Coffee Day | Federal House 

Tuesday, September 30 

Quickstart Mahjong | BD Provisions (September 30 & October 2)

Major Developments in American Constitutional History | Historic Annapolis: Virtual

Tom Sandoval & The Most Extras | Rams Head On Stage

Wednesday, October 1 

BD Provisions Book Club | BD Provisions

Navy Women’s Soccer vs Lehigh Game | Navy-Marine Corps Memorial Stadium

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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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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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