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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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Fall is calling… and so is dance season 🍂💙
Enrollment for the Ballet Theatre of Maryland Conservatory of Dance is officially OPEN! From your tiniest twirlers to dedicated dancers ready to level up, there’s something for every age and experience level.
With classes in both Annapolis and Grasonville, it’s easy to find the perfect fit for your schedule. Plus, students learn from professional instructors in a fun, supportive environment that builds confidence, creativity, and discipline (and helps burn off that after-school energy ✨).
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