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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

October 21, 2025 by Piper Langenfeld

Week of 10/23-10/29

Presented by

Thursday, October 23

Golden Gatherings are HERE. a pop-up shop | 6 Fleet Street (Oct. 23-Nov. 9)

Annual Fall Food Drive | Heritage Baptist Church (Oct. 23-31)

Great Annapolis Pumpkins | Downtown Annapolis (Oct. 23-31)

Share the Warmth at Annapolis Mall | Discoveries: Library at the Mall (Oct. 23-Nov. 30)

Friday, October 24

Social Bridge | Captain Avery Museum

Make Your Own Monster Pumpkin | Homestead Gardens: Davidsonville

Historic Annapolis Presents Printed in History: 260 Years of the Fatal Stamp Act | Hogshead Trades Museum 

Pumpkin Walk | Hammond-Harwood House 

Navy Women’s Soccer vs Lafayette Game | Navy-Marine Corps Memorial Stadium

Blue Crab Cupcakes 4th Annual Trunk or Treat | Blue Crab Cupcakes

Halloween Critter Crawl | Jug Bay Wetlands Sanctuary

Station 7 Terror Trail | Arundel Volunteer Fire Department (Oct. 24 & 25)

Bags, Bingo & Bourbon | Pip Moyer Recreation Center, Presented by: The Annapolis Police Foundation

Saturday, October 25

Annapolis Scarecrow Stroll | Downtown Annapolis (Oct. 25-Nov. 2)

Halloween Market | Wildberry Farm

Historic Annapolis Presents Mr. Paca’s Garden Storytime: Trick or Treat on Scary Street | William Paca House & Garden 

Fall Festival Weekends | Homestead Gardens: Davidsonville (Oct. 25 & 26)

The Pink Event | DoubleTree Hotel 

Historic Annapolis Presents Corsets & Contraband: African American Women’s Labor in the Fight for Freedom | Hogshead Trades Museum

Brian Glick NoGi Jiu-Jitsu Seminar | Kogen Dojo Annapolis 

Navy Football vs FAU (Homecoming) | Navy-Marine Corps Memorial Stadium 

Dinner Under the Stars: Masquerade Ball | Rams Head Tavern

Below Deck: Ghost Tales & Sea Shanties | Hammond-Harwood House 

O’Halloween Party | O’Loughlin’s Restaurant 

Watermark Presents Cruise to OysterFest in St. Michaels | Annapolis City Dock

Watermark Presents Kids Halloween Costume Cruises | Annapolis City Dock & Baltimore Finger Piers (Oct. 25 & 26)

Tall Tall Trees with Christopher Paul Stelling | Rams Head On Stage

Sunday, October 26 

Annapolis Crystals Presents Messages from Spirit with Two Mediums | 158 W Lake Drive 

Holiday Craft Fair | Earleigh Heights Fire Department 

Anchors & Artisans | Annapolis Town Center

Make Your Own Monster Pumpkin | Homestead Gardens: Severna Park 

The Sons of Pirates & Big Buffett Beach Band | Chesapeake Arts Center

Monday, October 27 

Women & Investing | CovingtonAlsina: Virtual 

Tuesday, October 28 

The Gunston School Presents the Mid-Shore College Fair | Chesapeake College 

Iam Tongi | Rams Head On Stage 

Wednesday, October 29 

Community Foundation of Anne Arundel County Presents the Celebration of Philanthropy Awards Luncheon | Live! Casino and Hotel 

Historic Annapolis Presents Orlando Ridout V Memorial Lecture | Governor Calvert House FASO Presents Dine to Donate | Maggiano’s Little Italy

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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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A little romance, a

A little romance, a little laughter, and a whole lot of Broadway magic are headed to Annapolis this November!

Live Arts Maryland is bringing the beloved music of Rodgers & Hammerstein's OKLAHOMA! to Maryland Hall for TWO special evenings celebrating one of the most iconic musicals of all time.

From Oh, What a Beautiful Mornin' to People Will Say We're in Love and The Surrey with the Fringe on Top, these are the melodies that have captured hearts for generations. And there's something especially wonderful about hearing them brought to life in concert!

Whether it's a longtime Broadway favorite or a first introduction to the music of Oklahoma!, this is a wonderful opportunity to enjoy timeless songs, beautiful storytelling, and a little Broadway nostalgia right here in Annapolis. ❤️

As a proud Annapolis Moms Community Supporter, Live Arts Maryland loves being part of a community that celebrates the arts and creates opportunities for local families to experience the joy of live music and theater together!

🎭 Rodgers & Hammerstein's OKLAHOMA!
📅 November 13 & 14, 2026 | 7:30 PM
📍 Maryland Hall | Annapolis, MD

Make it a date night, plan a fun evening with friends, or gather the musical theater lovers in the family. It's the perfect excuse for a night out in Annapolis! ✨

🎟️ Reserve your seats now!

#LiveArtsMaryland #AnnapolisMoms #OklahomaMusical #RodgersAndHammerstein #AnnapolisEvents
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