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Arts & Entertainment, Community, Do Not Miss

Save The Date List

August 16, 2026 by Piper Langenfeld

Wednesday, September 16

Anne Arundel County Fair | Anne Arundel County Fairgrounds (Sept. 16-20)

Friday, September 18

For the Love of the Library | Busch Annapolis Library 

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

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

Saturday, September 19

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

21st Annual Boatyard Beach Bash | Annapolis Maritime Museum

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

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

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 

Cyril Neville | Rams Head On Stage

Thursday, September 24

Historic Annapolis Presents Blazers . Bourbon . Cigars | William Paca House & Garden 

Brett Dennen | Rams Head On Stage 

Friday, September 25

All Things Go Music Festival | Merriweather Post Pavilion (Sept. 25-27)

Saturday, September 26 

Greater Crofton Chamber of Commerce Presents the Fall Festival on the Green | Crofton Country Club 

Navy Women’s Soccer vs. Colgate | United States Naval Academy 

Kunta Kinte Heritage Festival | Navy-Marine Corps Memorial Stadium

Sunday, September 27

Inner West Street Association Presents Oktoberfest | West Street, Annapolis

Ballet Theatre of Maryland and Historic Annapolis Present a La Sylphide Storytime | William Paca House & Garden 

Monday, September 28

Annapolis Area Christian School Athletic Golf Classic | The Golf Club at South River

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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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💙 Community Supporter: A Team Family Law, LLC

Divorce can be emotionally challenging—and financial decisions can add another layer of stress. When emotions are high, it’s easy to make financial choices that may have long-term consequences.

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8 WAYS TO SPEND YOUR WEEKEND AROUND ANNAPOLIS 👀
Live music, Halloween events, fall festivals, and a classic spooky tale on stage, there’s plenty happening around Annapolis from October 22–25!

Here’s what’s on the list:

🎶 The Live Spill at 49 West
🎃 KMA Law Office’s Halloween Spooktacular
🍬 Blue Crab Cupcakes’ 5th Annual Trunk or Treat
🎭 The Legend of Sleepy Hollow at The Colonial Players
🌽 Fall Fest at Greenstreet Gardens
🎸 Porchfest around Annapolis
🐾 Trick or Treat Trail at the SPCA
🎻 Naptown Philharmonic Orchestra’s Halloween Spooktacular

Plus, there’s more to explore throughout the weekend!

👉 See the full list here:
annapolismomsmedia.com/do-not-miss-list-oct-22/

#AnnapolisMoms #DoNotMissList #AnnapolisEvents #FallFun #WeekendPlans

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