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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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🍎 IT’S APPLE-PICKING SEASON!

Ready for a fall day at the farm? Grab the kids, bring a basket, and head out for some apple-picking fun!

From Baugher's Orchard and Butler's Orchard to Larriland Farm , Weber's Cider Mill Farm , and Homestead Farm , we rounded up some of the spots worth adding to your fall plans. 🍂

Just remember to check each farm’s website or socials before you go since picking availability can change with weather and crop conditions.

Save this guide for your next fall outing, and tag a friend you want to go apple picking with!

👉 See the full list here: annapolismomsmedia.com/your-ultimate-annapolis-guide-to-apple-picking/

#AnnapolisMoms #ApplePicking #FallFun #FamilyFun #WeekendPlans
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YOUR WEEKEND PLANS ARE HERE! 🍂

There’s plenty happening around Annapolis this weekend, from fall festivals and Oktoberfest to a heritage festival, book fair, and a special ballet storytime for little ones.

🎉 Fall Festival on the Green with @greatercroftonchamber
📚 AACLC Book Fair
🌍 Kunta Kinte Heritage Festival @kuntakuntefest
🍺 Oktoberfest with West Annapolis Business Association
🩰 La Sylphide Storytime with The Ballet Theatre of Maryland

And don’t miss Blazers . Bourbon . Cigars from Historic Annapolis on Thursday at the William Paca House & Garden.

For the little ballet fans, La Sylphide Storytime brings the classic ballet to life with dancers, a meet-and-greet, crafts, and refreshments also at the Paca House 🩰

Save this post, send it to your group chat, and start making plans!

👉 See the full list here: annapolismomsmedia.com/do-not-miss-list-sept-24/

#AnnapolisMoms #DoNotMissList #WeekendPlans #FamilyFun #LocalEvents
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