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Arts & Entertainment, Community, Do Not Miss

Save The Date List

September 27, 2026 by Piper Langenfeld

Thursday, October 29

Live Arts Maryland Golf Classic | Bay Hills Golf Club 

Candlelight: A Haunted Evening of Halloween Classics | Maryland Hall 

A multi-sensory, Halloween-themed music experience. 

Die Laughing Presents “Halloween Whodunit 3”: A Comedy Murder Mystery | Rams Head on Stage 

Friday, October 30

Pumpkin Walk | Hammond-Harwood House 

Kid-friendly activities and a costume parade. 

Disney’s Frozen the Broadway Musical | Children’s Theatre of Annapolis

Annapolis Opera Presents The Pirates of Penzance | Maryland Hall (Oct. 30-Nov. 1)

Sunday, November 1

The Gunston School Open House | The Gunston School

Inner West Street Association Presents the First Sunday Arts Festival | Downtown Annapolis

Wednesday, November 4

Gaelic Storm | Rams Head on Stage (Nov. 4-5)

Thursday, November 5

Historic Annapolis Presents a Visit to the Brandywine Museum of Art and N.C. Wyeth House & Studio: A Bus Tour | Maryland Hall

Friday, November 6

Game Night | iCode Gambrills

Saturday, November 7

Stride for SPAN 14th Annual Turkey Trot 5K/1M | Kinder Farm Park 

Appalachian Promotions Presents the Gun and Knife Show | Anne Arundel County Fairgrounds (Nov. 7-8)

Navy Football vs Temple | Navy-Marine Corps Memorial Stadium 

Sunday, November 8

Corrigan Sports Presents the Bay Bridge Run | Chesapeake Bay Bridge 

Makaya McCraven | Maryland Hall 

Tuesday, November 10

Retirement Homestretch | CovingtonAlsina: Virtual

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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-
of-annapolis/

#annapolismoms #LocalFoodFinds #fallflavors #coffeelovers
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