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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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Have you checked out our Maryland Day article yet? 👀🦀

We’ve rounded up 100+ ways to celebrate Maryland Day, from hands-on history and family-friendly festivals to boat cruises, crafts, and can’t-miss local events all week long. 🌼🎉

Whether you’re planning a day trip or filling your calendar, this is your go-to guide for everything happening around Annapolis and beyond!

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Sip & Stem: Spring Bouquet Class 💐

Grab your girlfriends (or treat yourself!) and join our Community Supporter on Thursday, April 2 | 7–8:30 PM at Julep Kitchen & Bar Annapolis for a fun and relaxed floral design night with The Wild Petal Society!

You'll create a beautiful spring arrangement to take home, enjoy a signature small plate, and sip a seasonal cocktail, mocktail, or glass of wine.

No experience needed, just come ready for a great night out! Spots are limited!

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Sip, snack, and design your own gorgeous floral arrangement at Julep Kitchen + Bar in Annapolis, MD! Join us Thursday, April 2nd at 7PM for a fun, hands-on workshop filled with pastel flowers, yummy b...
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