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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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Celebrate the holida

Celebrate the holidays with friends and family - Located right in the vibrant heart of Annapolis, Federal House Bar & Grille is so much more than just a fantastic restaurant—it’s the ultimate gathering place where friends, neighbors, and families come together to make memories! ⚓️👨‍👩‍👧‍👦

Need a spot to catch up? They've got you covered!
• Indulge in their DELICIOUS food! 🍔🍤
• Enjoy a toast and a laugh with friends over drinks! 🥂🍻
• Soak up that famous, fun, and LIVELY atmosphere! 🎶😎

If you’re looking for the PERFECT spot to connect with others this week, look no further! Stop by for an unforgettable meal, check out their incredible daily specials, or book your next party or event with them!

Thank you, Federal House, for being the fun, delicious cornerstone of our community and a dedicated community supporter!

📍 Find them here: 24 Market Space, Annapolis, MD 🔗 Check out their menu & details:https://www.federalhouse.com/
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🎄✨ Christmas Me

🎄✨ Christmas Menu 2025 is HERE! ✨🎄

Our incredibly talented Community Supporter Blue Crab Cupcakes is super excited to share their Christmas Menu for 2025! This year’s theme is Traditional Christmas & The Nutcracker and their team has poured so much love and creativity into crafting these magical, delicious desserts to make your holidays extra sweet. 💖🍰

📞 Call the Bakery to place your orders! 443-221-7246
🎁 Pickup Days:
• Dec 23rd: 11am–6pm
• Dec 24th: 11am–5pm

✨ Available BEFORE the official pickup dates:
• The Land of Sweets Cake
• Santa Cake
• Tree Cake
• Mini Cupcakes
• Small Tray
• Large Tray

📍 Blue Crab Cupcakes
1580 Whitehall Rd, Annapolis, MD 21409
(The Jemal Bay 50 Shopping Center on Rt 50)

We can’t wait to help make your holiday celebrations unforgettable! ❤️🎅🍬
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