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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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🍎 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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