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Arts & Entertainment, Community, Do Not Miss

Save The Date List

April 19, 2026 by Piper Langenfeld

Presented by:

Wednesday, May 20 

Dinner Under the Stars | 53 West Street, Annapolis

Blue Angels Show | Severn River and Annapolis

Thursday, May 21

DelFest | Cumberland (May 21-24)

Friday, May 22

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

Saturday, May 23

Artscape | Downtown Baltimore (May 23-24)

Historic Annapolis Presents the Paca Garden Guided Tour | William Paca House & Garden

Monday, May 25

Memorial Day Celebration | Federal House 

Tuesday, May 26

Andrew Duhon: Stop Motion Tour | Rams Head On Stage

Friday, May 29

Nico’s Golf 4 Hope Tournament | Queenstown Harbor Golf Course 

B.I.G. Book Sale | Books for International Goodwill Warehouse (May 29-30)

Annapolis Irish Festival | Anne Arundel County Fairgrounds (May 29-30)

Greater Annapolis Ballet Presents Playlist En Pointe | Maryland Hall 

Saturday, May 30

National Music Festival | Various Locations (May 30-June 13)

Annapolis Greek Festival | Sts. Constantine & Helen Greek Orthodox Church (May 30-31)

Annapolis Homebrew Club Presents Pints 4 Paws | Navy-Marine Corps Memorial Stadium 

Annapolis Blues vs. Charlottesville Blues FC (W) | Navy-Marine Corps Memorial Stadium

Annapolis Blues vs. Virginia Beach United (M) | Navy-Marine Corps Memorial Stadium 

jackrabbit. featuring Dermot Mulroney & Kieran Mulroney | Rams Head On Stage

Youth Chorus of Annapolis Spring Concert | Annapolis Area Christian School

Sunday, May 31

Anne Arundel Asian American Festival | Anne Arundel County Fairgrounds 

Maryland Federation of Art Presents Paint Annapolis | Downtown Annapolis (May 31-June 7)

Hot Wheels Monster Trucks Live Glow-N-Fire Tour | CFG Bank Arena  

Monday, June 1

Providence’s Moran Golf Classic | Queenstown Harbor Golf Course

Annapolis Symphony Academy and Orchestra Present Shostakovich Symphony No. 5 | Joseph Meyerhoff Symphony Hall 

Wednesday, June 3

Annapolis Blues vs Lionsbridge FC (M) | Navy-Marine Corps Memorial Stadium

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Related posts:

Save The Date List Eye on Annapolis: Weekly Round-Up Eye on Annapolis: Weekly Round-Up Eye on Annapolis: Weekly Round-Up
Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

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Previous Post:The Real Mom April Recap

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Rainy day plans = handled ☔️✨ From indoor play spots to creative escapes, this guide is packed with fun ways to keep the kids entertained no matter the weather.

Check out Rain or Shine Family Fun for 5 go-to spots to save your next spring shower day!

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💙 Peace of mind for your family starts at home 💙

If you have a loved one who needs a little extra support, our community supporter Angel Care Network is here to help.

Their compassionate team provides personalized in-home care so seniors and individuals can remain safe, comfortable, and independent right where they belong, at home. From companionship and daily support to more hands-on personal care, every plan is thoughtfully tailored to each family’s needs.

✨ Trusted. Experienced. Truly caring.

Whether you need a few hours of help or ongoing care, their “Angels” treat your loved ones like family—because they know how much that matters.

📍 Serving Annapolis & surrounding areas
📲 Learn more or schedule a free consultation:

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