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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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May Day in Downtown Annapolis 🌸✨ Flower baskets, fresh blooms, and all the springtime charm, there’s no better day to wander, shop, and soak it all in!

If you’re out and about, stop into @fedhousebar to check out our stunning floral installation by @studiohfloraldesign , then spend the evening with Annapolis Moms from 5–7 right out front for a fun, feel-good happy hour, mention Annapolis Moms and 10% of your purchase goes to FOAM, which provides emergency support to local families when they need it most 💛
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🌿🌸 Looking for the perfect Mother’s Day weekend activity? Don’t miss the 52nd Annual @historicannapolis Plant Sale at the beautiful William Paca Garden!

🌷Event Details:
Saturday, May 9: 10:00 AM – 4:00 PM (Enter at 186 Prince George St)
Sunday, May 10: 12:00 PM – 4:00 PM (Enter at 3 Martin St)

🌼 Shop from 8,000+ plants—including perennials, annuals, veggies, trees, vines, and native plants.

✨ Highlights include:
• Native and pollinator-friendly plants
• Unique varieties like zinnias, foxglove, and hydrangeas
• Kitchen garden favorites (hello, Italian peppers & melon!)
• NEW curated plant collections (sun, shade & native)
• Expert gardeners onsite to help you plan your space

💚 Free admission + every purchase supports Historic Annapolis’ preservation efforts

🌟 Member Perks: Early access (9:30 AM Saturday) + 10% off plants all weekend

Whether you’re a seasoned gardener or just getting started, this is a can’t-miss local tradition!

👉 Learn more & become a member:
www.annapolis.org
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