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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

May 12, 2026 by Piper Langenfeld

Week of 5/14-5/20

Presented by

Thursday, May 14

42nd Street | Classic Theatre of Maryland (May 14-17)

Friday, May 15

Ballet Storytime & Preview | Eastport-Annapolis Neck Library 

Saturday, May 16

Infinite Hero Presents 22 Miles to Break Boundaries | Annapolis High School (May 16-17)

Flea Market & Craft Sale | Anne Arundel County Fairgrounds

Historic Annapolis Presents Mr. Paca’s Garden Storytime: Mommy Time | William Paca House & Garden (May 16 & 19)

Spring Craft Fair | Earleigh Heights Fire Department 

Kent Island Heritage Society Presents Kent Island Day | 408 Love Point Road, Stevensville 

Gaithersburg Book Festival | Bohrer Park 

Chesapeake Catfish Cook-Off | Annapolis Maritime Museum: Park Campus

Armed Forces Day Concert | United States Naval Academy: Radford Terrace  

Put it in the Pock3t | Maryland Hall 

The Blue Ribbon Bash | Severna Park Elks Lodge

A Musical Melting Pot | Live Arts Studio

The Erin Levitas Foundation Presents a Stroll & Roll | Camden Yards Sports Complex

The Lone Bellow | Rams Head On Stage

Sunday, May 17

Makers of Maryland Presents the Anchors & Artisans Pop-Up Market | Annapolis Town Center 

Burgers & Bands for Suicide Prevention | Severna Park Taphouse 

Taste of Spring on West Street | 53 West Street, Annapolis

The Talent Machine Company Presents a Cash Bingo Bonanza | Glen Burnie Elks Lodge 

Annapolis Symphony Academy Day | Maryland Hall 

Monday, May 18 

Emerald Society Golf Tournament | Walden Country Club 

Wednesday, May 20

Blue Angels Paddle | Capital SUP Eastport 

Blue Angels Show | Annapolis

Dinner Under the Stars | 53 West Street, Annapolis

Chantal Kreviazuk | Rams Head On Stage

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

About Piper Langenfeld

Previous Post:Annapolis Moms Deal Drop | May 12, 2026
Next Post:Eye on Annapolis: Top 6 in the News | May 13, 2026 |

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School’s Out Night THIS Wednesday 📚☀️

Kickoff the summer in style with YOUR Annapolis Blues at School’s Out Night this Wednesday at 7:00 pm against Hill City FC 🫡

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📚☀️ The final

📚☀️ The final bell has rung and summer officially starts this Wednesday!

Kick off break with the Annapolis Blues as they take on Hill City FC at 7 PM for School’s Out Night. Grab the family, wear your blue, and celebrate the start of summer with an evening of exciting soccer, great energy, and plenty of fun at the stadium. ⚽💙

Who’s ready to trade homework for game day? 🙌

🎟️ Tickets available at annapolisblues.com
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