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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

September 14, 2025 by Piper Langenfeld

Week of 9/18-9/22

Presented by

Thursday, September 18 – Sunday, September 21 | PopUp! Inflatable Art Festival | Pikesville Armory

Thursday, September 18 | National Cheeseburger Day | Federal House

Thursday, September 18 | TNF Bills vs Miami and Live Music from Tim & Katie | O’Loughlin’s Restaurant 

Thursday, September 18 | Colonial Cocktails: Medicinal Mixers | Historic London Town & Gardens

Friday, September 19 | Women in Business Networking Event | Trendy Tides Boutique & Annapolis Crystals

Friday, September 19 | For the Love of the Library | Busch Annapolis Library

Friday, September 19 | Calm for a Cure Launch Party | Pherm Brewing Company 

Friday, September 19 | Baygrass Kickoff Party | Maryland Hall

Friday, September 19 | Watermark’s Annapolis Sunset Cruise with Chris Sacks (Duo) | Annapolis City Dock

Saturday, September 20 & Sunday, September 21 | Gun and Knife Show | Anne Arundel County Fairgrounds 

Saturday, September 20 | Solar Eclipse in Virgo Past Life Regression | 158 West Lake Drive 

Saturday, September 20 | Mr. Paca’s Garden Storytime: Library Girl | William Paca House & Garden

Saturday, September 20 & Sunday, September 21 | Women’s Work Weekend | Historic London Town & Gardens

Saturday, September 20 | March to Revolution | Pinkney Street

Saturday, September 20 & Sunday, September 21 | Annapolis Baygrass Music Festival | Sandy Point State Park 

Saturday, September 20 | Navy Women’s Soccer vs Boston University Game | Navy-Marine Corps Memorial Stadium

Saturday, September 20 | Boatyard Beach Bash | Annapolis Maritime Museum

Saturday, September 20 | Maysa | Rams Head On Stage

Saturday, September 20 | Watermark’s African American Heritage Tour | Market House Park 

Sunday, September 21 | Muaythai Development League | Benfield Sportscenter

Sunday, September 21 | Together in Teal | Annapolis Mall

Sunday, September 21 | Annapolis Italian Fall Festa | Sons and Daughters of Italy

Sunday, September 21 | Inaugural Corn-Hooley & Shamrock Shenanigans | Earleigh Heights Fire Station

Sunday, September 21 | Music of the Americas | Maryland Hall 

Sunday, September 21 | Ballet in the Garden | Hammond-Harwood House 

Sunday, September 21 | Comedian Michael Yo | Rams Head On Stage

Sunday, September 21 | Priddy Music Academy Performance | Market Space at Federal House

Monday, September 22 | Retire on Purpose | CovingtonAlsina: Virtual

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Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

About Piper Langenfeld

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