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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

May 19, 2026 by Piper Langenfeld

Week of 5/21-5/27

Presented by

Thursday, May 21

DelFest | Cumberland (May 21-24)

Color Parade | United States Naval Academy 

Historic Annapolis Book Club | Museum of Historic Annapolis 

Colonial Cocktails: Society Sippers | Historic London Town & Gardens

Die Laughing Productions Presents a “Hit Me 90s One More Time” Comedy Murder Mystery | Rams Head On Stage

Friday, May 22

United States Naval Academy Graduation | Navy-Marine Corps Memorial Stadium

Academy Ballet School of Annapolis Presents: The Little Mermaid | Maryland Hall (May 22-23)

Paul Cullen: Good Times with Bad Company | Live Arts Studio

Saturday, May 23

Artscape | Downtown Baltimore (May 23-24)

Arundel Bands Together | Arundel High School 

Dancing Stories with Kalanidhi Dance | Eastport-Annapolis Neck Library

Sunday, May 24

Oak Crest Farmers’ Market | Oak Crest Farm 

Monday, May 25

City of Annapolis Presents the Memorial Day Parade | Amos Garrett Boulevard and West Street, Annapolis

Memorial Day Celebration | Federal House 

Wednesday, May 27

Homeschool Lunch & Learn: Unlocking the Universe with NASA| Severna Park Library

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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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We hope everyone has an amazing day watching the Blue Angels soar over Annapolis! 💙✈️ There’s truly nothing like this week in our city.

And once the planes clear, the fun keeps going 🎉 Our latest Do Not Miss List is packed with concerts, festivals, comedy, parades, ballet, cocktails, markets, and so much more happening all week long around Annapolis and beyond.

Check out the full list at the link in our bio + below and start planning your next adventure! 🔗

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