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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

May 27, 2025 by Piper Langenfeld

Week of 5/28/25 – 6/4/25

Presented by

Thursday, May 29 | Hot Sips & Divorce Tips | Betty Center

Thursday, May 29 | Art Night: The Truth About Dragons | Severna Park Library

Thursday, May 29 | The Local Singer/Songwriter Round | Cult Classic Brewing Company

Thursday, May 29 | Live Music from Jack Rimel | O’Loughlin’s Restaurant

Friday, May 30 | Golf 4 Hope Tournament | Queenstown Harbor Golf Course

Friday, May 30 | Bug Ball | Discoveries: The Library at the Mall

Friday, May 30 | Blood, Sweat & Tears | Maryland Hall 

Friday, May 30 | Josh Radnor (Star of How I Met Your Mother) with Michaela Anne | Rams Head On Stage

Saturday, May 31 | Force Dance Company Auditions | Creative Force Dance Center

Saturday, May 31 & Sunday, June 1 | Living History Weekend: Plain and Fancy Sewing | Historic London Town & Gardens

Saturday, May 31 – Sunday, June 1 | Annapolis Greek Festival | Ss. Constantine & Helen Greek Orthodox Church

Saturday, May 31 | Annapolis Pride Parade & Festival | Downtown Annapolis and Maryland Hall

Saturday, May 31 | Pints 4 Paws | Navy-Marine Corps Memorial Stadium

Saturday, May 31 | Annapolis Blues vs Christos FC (M) | Navy-Marine Corps Memorial Stadium 

Saturday, May 31 | Annapolis Blues vs Richmond Ivy (W) | Navy-Marine Corps Memorial Stadium

Sunday, June 1 – Sunday, June 8 | Paint Annapolis | Annapolis

Sunday, June 1 | First Sunday Arts Festival | Inner West Street

Sunday, June 1 | Basic Guitar Maintenance Workshop | Bach to Rock: Severna Park

Sunday, June 1 | Maryland Crab Feast Cruise | Baltimore Finger Piers

Sunday, June 1 | Writer’s Workshop | Historic London Town & Gardens

Sunday, June 1 – Saturday, June 7 | National Music Festival | Chestertown

Monday, June 2 – Saturday, June 7 | Summer Book Bags | Discoveries: The Library at the Mall 

Monday, June 2 | Providence of Maryland’s 32nd Annual Moran Golf Classic | Queenstown Harbor Golf Course

Monday, June 2 | American Red Cross Blood Drive | Busch Annapolis Library

Tuesday, June 3 | Mr. Paca’s Garden Storytime: “How to Surprise a Dad” | William Paca House & Garden 

Tuesday, June 3 | Music Immersion | Naptown Sings and Plays!

Tuesday, June 3 | Free Screening: A Roadkill Opera | Cult Classic Brewing Company 

Tuesday, June 3 – Sunday, June 8 | Chicago the Musical | The Hippodrome Theatre

Wednesday, June 4 – Saturday, June 7 | Santa Maria Cup | Eastport Yacht Club 

Wednesday, June 4 | Storytime | The Big Bean Coffee House

Wednesday, June 4 | Live Music with Anton Tuvelman | Twain’s Tavern

Wednesday, June 4 | Ted Vigil: A Tribute to John Denver | Rams Head On Stage

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Related posts:

Eye on Annapolis: Weekly Round-Up Eye on Annapolis: Weekly Round-Up Where the He!% did our money go? Eye on Annapolis Weekly Round Up: Fraudulent Doula Services + Annapolis Porchfest
Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

About Piper Langenfeld

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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.

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