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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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Our Community Suppor

Our Community Supporter, Davy Dance Academy, is bringing a little holiday magic to the stage with their Polar Express Holiday Musical! 🚂✨

🎟️ Tickets are on sale now!
📅 Saturday, December 19, 2026
⏰ 2:00 PM & 6:00 PM
📍 Anne Arundel Community College
🎫 Tickets: $15 kids (ages 2–12) & $20 adults

🔗 Get your tickets here: 22055.recitalticketing.com

We love seeing local businesses like Davy Dance Academy bring our community together through the arts. ❤️

#AnnapolisMoms #AnnapolisDance #HolidayMusical
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A LITTLE CULTURE, A LITTLE COMEDY, AND SOME HOLIDAY SHOPPING — WHAT’S ON YOUR WEEKEND CALENDAR? 👀

There’s a good mix of things happening around Annapolis this weekend, from live performances and local shopping to wine tastings and a celebration of Indigenous arts.

Here’s what’s coming up November 13–15:

🎭 Oklahoma! at Maryland Hall
🍷 Tastings & Tunes: Wine & Beer Fest on West
🎁 Holiday Pop-Up Shop at Severna Park Community Center
😂 Comedian Paul Mecurio at Rams Head on Stage
🥁 Uhwachi-Reh Indigenous Arts at Pip Moyer Recreation Center

There’s a little something for every kind of weekend plan, so take your pick and get those dates on the calendar!

👉 See the full Do Not Miss List here: annapolismomsmedia.com/do-not-miss-list-november-12-2026/

#AnnapolisMoms #DoNotMissList #AnnapolisEvents #WeekendPlans #ThingsToDoAnnapolis
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