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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

May 19, 2026 by Piper Langenfeld

Week of 5/21-5/27

Presented by

Thursday, May 21

DelFest | Cumberland (May 21-24)

Color Parade | United States Naval Academy 

Historic Annapolis Book Club | Museum of Historic Annapolis 

Colonial Cocktails: Society Sippers | Historic London Town & Gardens

Die Laughing Productions Presents a “Hit Me 90s One More Time” Comedy Murder Mystery | Rams Head On Stage

Friday, May 22

United States Naval Academy Graduation | Navy-Marine Corps Memorial Stadium

Academy Ballet School of Annapolis Presents: The Little Mermaid | Maryland Hall (May 22-23)

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

Saturday, May 23

Artscape | Downtown Baltimore (May 23-24)

Arundel Bands Together | Arundel High School 

Dancing Stories with Kalanidhi Dance | Eastport-Annapolis Neck Library

Sunday, May 24

Oak Crest Farmers’ Market | Oak Crest Farm 

Monday, May 25

City of Annapolis Presents the Memorial Day Parade | Amos Garrett Boulevard and West Street, Annapolis

Memorial Day Celebration | Federal House 

Wednesday, May 27

Homeschool Lunch & Learn: Unlocking the Universe with NASA| Severna Park Library

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

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🍂 PUMPKIN SPICE AND EVERYTHING NICE! ☕

Fall calls for cozy sweaters, crisp air, and a coffee that tastes like the season. From pumpkin spice lattes and maple cream cold brews to apple chai and snickerdoodle drinks, local
Annapolis-area cafés are serving up plenty of fall flavors worth trying.

We rounded up our favorite stops for seasonal sips, sweet treats, and cozy café vibes, including beanrushcafe The Big Bean Brown Mustache Coffee™ Ceremony Coffee Roasters Kozy Beans Coffee - Crofton, MD Rise Up Coffee Roasters and Wyrd Bookstore

Save this guide for your next coffee run, and tag your fall coffee buddy!

👉 Read the full guide here: annapolismomsmedia.com/our-fall-flavor-coffee-tour-
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