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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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Maryland weather can

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📸 Annapolis has no shortage of picture-perfect spots ✨

From charming downtown streets and waterfront views to beautiful gardens and scenic parks, we rounded up some of the best places around Annapolis for family photos, senior portraits, milestone moments, and capturing memories with the people you love 💛

If you’ve been planning updated photos or looking for a gorgeous local backdrop, this is one to save. What are some of your favorite photo spots? Comment below.

🔗 Full roundup is linked in our bio + below!
annapolismomsmedia.com/the-perfect-places-to-pose-the-best-spots-for-photos-in-annapolis/

#AnnapolisMoms #AnnapolisMD #VisitAnnapolis #FamilyPhotos #AnnapolisPhotographer
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