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Community

It’s the Great Pumpkins, Annapolis

October 12, 2025 by Ricky Hartford

Annapolis is fall-ing for pumpkins all over again! The Great Annapolis Pumpkins have returned this October, turning downtown into a festive, photo-worthy pumpkin patch filled with giant gourds that would make even Charlie Brown say, “Now that’s the Great Pumpkin!”

These aren’t your average porch pumpkins. They’re real and really big, tipping the scales at up to 1,500 pounds each. Find them all around downtown at:

  • Annapolis Visitors Center
  • St. Anne’s Episcopal Church
  • St. John’s College
  • Maryland Avenue
  • Market Space
  • Museum of Historic Annapolis
  • Annapolis Waterfront Hotel
  • Main Street at Francis Street

Stroll the streets with your family, take some pumpkin-perfect photos, and don’t forget to tag @VisitAnnapolis so we can see your squash goals. Just remember, no climbing or carving yet. These gentle giants bruise easily before their big transformation.

🎃 Save the Date

On Friday, October 24, professional artists, including Food Network’s Halloween Wars star Nancy Baker, will turn these beauties into the area’s largest Jack-o’-Lanterns. It’s a spectacle that’ll have you glowing inside and out.

Scarecrow Stroll

And the fun doesn’t stop there. From October 25 through November 2, the 4th Annual Annapolis Scarecrow Stroll will line the streets with creativity and community spirit. Stroll through downtown to see scarecrows created by local families, businesses, and organizations along West Street from circle to circle, Main Street, Maryland Avenue, and State Circle. Vote for your favorite or even make one yourself—registration is open until October 17.

So grab your cozy sweater, your camera, and maybe a pumpkin treat or two, and come see what all the gourd fuss is about.

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Related posts:

Do Not Miss List A Bushel of Fun: Your Guide to Local Apple Orchards Vital YouYour Health Provider Can be a Health Partner Kids trick or treating and running10 Trunk-or-Treats Coming Up In The Annapolis Area
Category: CommunityTag: Downtown Annapolis, Fall, pumpkin See all posts by Ricky Hartford

About Ricky Hartford

Ricky Hartford is fueled by cold brew, Celtics highlights, pop culture, and a perfectly placed Oxford comma. By day, he works in marketing and communications at Anne Arundel Community College, where he helps shape the college’s voice through content and storytelling. With over a decade of experience and a Master of Science in Strategic Communications, he’s helped nonprofits and local publications sound sharper, look better, and connect more clearly with their audiences. When he’s not working, he’s probably at the movies, on the basketball court, planning his next vacation, or convincing someone (anyone) to talk about the latest trashy reality show. Annapolis is his happy place, especially if it involves a drink downtown and hanging out by the water.

Previous Post:Fall on Tap: Brews and Bites in Annapolis
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⚾️ SUMMER NIGHTS

⚾️ SUMMER NIGHTS ARE BETTER AT THE BALLPARK! ⚾️

Looking for something fun to do with the kids? Grab the family and head out to cheer on our Annapolis Moms Community Supporter, the Chesapeake Baysox! 🧡⚾️

A Baysox game is so much more than baseball. Between the action on the field, ballpark food, kids’ activities, special theme nights, giveaways, and plenty of opportunities to get up and cheer, there’s something happening all night long. It’s an easy, family-friendly outing that kids AND parents can get excited about!

And you definitely don’t want to miss Navy Night this Friday, July 24 at 7:05 PM, celebrating the USNA Class of 2030 and wrapping up the night with fireworks! 🎆⚓️

Whether your kids are huge baseball fans or just there for the snacks, mascot and fun, a night with the Baysox is such a great way to make a few more summer memories together.

⚾️ Grab your tickets, bring the kids, and get ready to root, cheer, snack and PLAY BALL!

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☀️ YOUR WEEK JUST GOT A WHOLE LOT MORE FUN! 🙌
The latest Do Not Miss List is here, and July 23–29 is packed with reasons to get out of the house and enjoy summer! 🎶🌊

From live music and Baysox baseball ⚾ to pop-up shopping, pizza + playtime, a full moon paddle, outdoor concerts, and more. There’s something happening for everyone this week around Annapolis.

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

👉 Check out the full Do Not Miss List LINKED in our bio and below and don’t miss a thing!

annapolismomsmedia.com/do-not-miss-list-7-22-26/

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