HALLOWEEN HAPPENINGS AROUND ANNAPOLIS

HALLOWEEN HAPPENINGS AROUND ANNAPOLIS

The Great Annapolis Pumpkins

Downtown Annapolis | Through November 2

One of my favorite seasonal traditions! Giant pumpkins make their appearance throughout downtown Annapolis, creating the perfect backdrop for festive photos, a leisurely stroll, and perhaps a stop at your favorite local coffee shop or restaurant.

Annapolis Scarecrow Stroll

Downtown Annapolis | October 24 – November 2

Take a walk through downtown and enjoy creative scarecrow displays along West Street, Maryland Avenue, and State Circle. It's a fun way to experience the charm of Annapolis dressed up for fall.

Halloween Spooktacular

Severna Park Community Center | Friday, October 23 | 5–8 PM

A festive, family-friendly evening filled with Halloween games, crafts, costumes, and seasonal activities. A wonderful option for families with younger children.

Kinder Farm Park Trunk or Treat & Costume Contest

Millersville | Saturday, October 24 | 11 AM–3 PM

Costumes, candy, and plenty of Halloween spirit! This family-friendly event combines the fun of trick-or-treating with one of Anne Arundel County's favorite parks.

SPCA Trick or Treat Trail

Annapolis | October 24–25 | Noon–4 PM

Calling all animal lovers! Enjoy a Halloween-themed outing while supporting the SPCA of Anne Arundel County. A particularly fun way to celebrate the season with children who adore animals.

👻 A LITTLE SOMETHING SPOOKY

The Legend of Sleepy Hollow

The Colonial Players, Annapolis | October 23 – November 8

Looking for a fall date night or a fun evening with friends? Enjoy a theatrical interpretation of Washington Irving's classic tale of Ichabod Crane and the Headless Horseman.

Historic Annapolis Ghost Tours

Downtown Annapolis | Select October Evenings

With centuries of history, charming cobblestone streets, and historic buildings, Annapolis provides the perfect setting for a ghost tour.

Explore local legends, mysterious stories, and the spookier side of our beautiful historic city.

Pumpkin Walk at Hammond-Harwood House

Annapolis | Friday, October 30

Celebrate Halloween at one of Annapolis's beautiful historic properties with seasonal activities, storytelling, crafts, and family fun.

🍎 PUMPKIN PATCHES & FALL FARM ADVENTURES

Sometimes the best fall memories are the simplest ones: finding the perfect pumpkin, wandering through a corn maze, enjoying a hayride, or spending an afternoon outside with the people you love.

Here are a few ideas for your fall bucket list:

Pumpkin Picking in Davidsonville

Head out to the countryside for a more relaxed fall experience, complete with pumpkins, fresh air, and beautiful rural scenery.

Fall Farm Festivals Around Anne Arundel County

Look for local farms offering corn mazes, hayrides, seasonal treats, and activities for the whole family. Be sure to check each farm's schedule before visiting.

A Scenic Fall Drive Through South County

One of my favorite things about this area is how quickly you can leave the bustle of downtown Annapolis behind and find yourself surrounded by beautiful farmland, winding roads, and autumn colors.

Pack a coffee, take the scenic route through Davidsonville, Harwood, Lothian, and the surrounding communities, and enjoy the quieter side of Anne Arundel County.

🍁 MY PERFECT ANNAPOLIS FALL DAY

If you're looking for a simple way to spend a beautiful fall afternoon, here's my suggestion:

Start with coffee downtown, take a stroll to see the giant pumpkins and scarecrows, enjoy lunch at one of our wonderful local restaurants, and finish with a walk along the waterfront.

There's something about watching the boats on Spa Creek with the crisp autumn air that never gets old.

And if you're feeling adventurous, book an evening ghost tour to end the day!

❤️ A LITTLE NOTE FROM KATIE

One of the things I love most about living and working in Anne Arundel County is the incredible sense of community.

We have the charm and history of Annapolis, the beauty of the Chesapeake Bay, wonderful local businesses, and so many traditions that make this area feel like home.

As a real estate agent, I have the privilege of helping people find their place in this community. But for me, real estate has always been about so much more than houses.

It's about the lifestyle, the memories, the neighbors, and the little moments that make a place special.

I hope this guide inspires you to get out, explore, support our local businesses, and make some wonderful fall memories.

Wishing you and your family a beautiful autumn and a very happy Halloween!

Cheers,

Katie Moore
Engel & Völkers Annapolis 

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Event dates, times, admission, and availability are subject to change. Please confirm details with event organizers before attending.