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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 Default ThumbnailA 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.

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We got to check it out… and WOW! 🤩🏀⚾️

The Annapolis Moms Crew had a chance to check out the brand-new DICK’S House of Sport at Annapolis Mall, and let’s just say… this is NOT your average sporting goods store!

From sneakers and athletic apparel to equipment for just about every sport you can think of, there is SO much to see. And the best part? It’s designed to be an experience, not just a place to grab a pair of sneakers and leave.

Whether you have a serious athlete in your family, a kid who is constantly trying a new sport, or you’re just looking for some new gear, there’s something here for everyone. 🏃‍♀️🏀⚽️🎾

We loved getting a first look and checking everything out—and we think your family is going to have a LOT of fun here, too! Plus you can host Birthday Parties here!

📍 DICK’S House of Sport | Annapolis Mall

Have you been yet? Tell us what you think! 👇

#AnnapolisMoms #AnnapolisMD #AnnapolisMall #DicksHouseOfSport #Annapolis #FamilyFun #ShopLocal
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Batter up ⚾️

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Batter up ⚾️

The Chesapeake Baysox are bringing in the winter early on Saturday, September 5!

Head out to the ballpark for a family friend night feature former Washington Capitals players, with the NHL season right around the corner! 🏒 #communitysponsor #proudAnnapolisMomsSponsor #baseball #hockey #family

Head to the link below to purchase your tickets!

www.ticketreturn.com/TRMobile//tickets/choose-tickets/choose-section?EventID=358297&adobe_mc=...
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