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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

September 15, 2026 by Piper Langenfeld

Week of 9/17-21

Thursday, September 17

Historic Annapolis Book Club: The Rediscovery of America: Native Peoples and the Unmaking of U.S. History | Museum of Historic Annapolis

K-12 Information Night | Annapolis Area Christian School

Friday, September 18

Anne Arundel County Public Library Foundation Presents For the Love of the Library | Busch Annapolis Library 

A fundraiser for AACPL with an author event, an auction, and food.

Official Baygrass Kick-Off Party with Jammy Buffet | Maryland Hall 

Compass Rose Theater Presents You’re a Good Man, Charlie Brown | Live Arts Studio (Sep. 18-Oct. 4)

Davy Knowles Band | Rams Head on Stage

Saturday, September 19

Annapolis Baygrass Music Festival | Sandy Point State Park (Sep. 19-20)

Oktoberfest Kickoff Party | Garten 

A Stein holding competition and a live polka band. 

Adopt a Homeless Animal Rescue Inc. Presents Yappy Hour | Severna Park Taphouse 

Meet adoptable dogs. 

Navy Men’s Soccer vs Boston U. | United States Naval Academy: Glenn Warner Soccer Facility 

Pickle Fest | Glen Burnie Elks Lodge #2266

21st Annual Boatyard Beach Bash | Annapolis Maritime Museum & Park 

Ballet Theatre of Maryland Presents Ballet in the Garden | Hammond-Harwood House 

Parents’ Night Out | Center Lane Swim School

Swimming, food, and games for kids. 

Ladies Night Out | Hansel Hill Farm

Yoga and flower arranging. 

Naptown Philharmonic Orchestra Presents ¡Viva La Música! A Night of Fire & Flair | Maryland Hall 

Sam Grisman Project | Rams Head on Stage

Sunday, September 20

Annapolis RUN for The Light House | Quiet Waters Park 

Makers of Maryland Presents the Anchors & Artisans Pop-Up Market | Annapolis Town Center 

Naptown Vinyl Record Market | Maryland Hall 

Emerald Society Presents The Corn-Hooley & Shamrock Shenanigans Festival | Earleigh Heights Fire Department 

Monday, September 21

Generational Wealth Transfer | CovingtonAlsina: Virtual

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Related posts:

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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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Football season is here, and our Community Supporter KISS MY GLASS Window Cleaners is proud to be part of getting Navy-Marine Corps Memorial Stadium ready for kickoff!

One of their favorite jobs of the summer is making sure this iconic stadium is looking its best before the Midshipmen take the field.

From glass to game day, Kiss My Glass is proud to be a Veteran-owned business serving our community!

️ GO NAVY! BEAT ARMY!

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Our community supporter Angel Care Network provides compassionate in-home care that goes beyond helping with everyday tasks. Their caregivers also provide the conversation, connection, and companionship that can help seniors feel engaged, supported, and less alone.

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