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Arts & Entertainment, Halloween, Holiday

The Great Annapolis Pumpkins: You Gourda’ See This!

October 23, 2023 by Frank Bolinsky
Pumpkin Montage
These pumpkins are massive–we had fun trying to lift, hug, ride, and sail them.
If you post your pictures and tag them appropriately (#GreatAnnapolisPumpkins, #VisitAnnapolis, and #VisitMaryland), you will be entered to win gift cards from downtown businesses.

There have been a lot of posts recently about the Great Annapolis Pumpkins, so I felt the need to pack up the family and check it out! Eight very large pumpkins have been placed around Annapolis, a few of which are over 1000 pounds! My kids love the whole concept of a scavenger hunt, so they were on board.

Map it Out
The locations are as follows: Graduate Annapolis Hotel, Annapolis Visitors Center, St. Anne’s Episcopal Church, Maryland Inn, Maryland Avenue at State Circle, Market House, Annapolis Waterfront Hotel, and Boatyard Bar & Grill.

Scarecrow Montage
A fun surprise–search for scarecrows while on the pumpkin path.

I mapped them out on Google maps ahead of time and confirmed that if you see them in that order, then you are on the most direct path. If you want to see them all, it is close to a 3-mile walk round trip. If you opt out of the Boatyard Bar & Grill pumpkin, you shave off one mile. We parked at Gott’s Garage, because it’s easy in and easy out of downtown, plus it is right next to the Visitor Center.

Follow the Trail
We got on West Street, turned right (away from Church Circle), and walked up until we got to the Graduate Hotel and started our journey there. We made our way down to each pumpkin until we had two left and then we got lunch at The Choptank (first time there for us). We then hit up the pumpkin outside of Pusser’s, debated what to do about the last one, caved and walked over the bridge to Boatyard, and then made our way back to the car.

Great Annapolis Pumpkin

If you post your pictures and tag them appropriately #GreatAnnapolisPumpkins, #VisitAnnapolis, and #VisitMaryland, you will be entered to win gift cards from downtown businesses.

Seeing all of the pumpkins plus a sit-down lunch took 2.5 hours for us. I felt the three most unique were the ones right by the Market House (seemed to be the largest), by Pusser’s (was decorated with a pirate), and the corner of Maryland Avenue and State Circle (it was a different color). The pumpkins are currently not carved, but will be carved starting October 27th and we may opt to go back down.

Follow this route for the most efficient way to see all the pumpkins!

Scarecrows, too!
Another fun activity that was a surprise to us was when we realized the Inner West Street Association had created a Scarecrow Stroll where there are scarecrows hidden everywhere along a similar path. There are 30 scarecrows, all with different themes, and they are hanging around through Halloween.

This fun walking tour made for a great family outing on a beautiful, breezy Sunday morning.

The Great Annapolis Pumpkins: You Gourda’ See This!

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Category: Arts & Entertainment, Halloween, HolidayTag: Activities, Family Friendly, Halloween, Outdoors, pumpkin See all posts by Frank Bolinsky

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🎭 Our amazing Annapolis Moms Community Supporter, The Talent Machine Company, is bringing the mystery, music, and fun to the stage this summer!

The reviews are in, and The Talent Machine’s production of Curtains is "pure entertainment...with a wonderfully talented teenage cast. Audiences are sure to walk away with a renewed appreciation for the magic of musicals." See for yourself! Four shows left of Curtains: A Musical Comedy Whodunit: July 16, 17, 18 & 19. Tickets just $20. Don't miss the mystery, the mayhem, the music -- and the incredible dancing!

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🚨 SAVE THE DATE: The Puppy Plunge is BACK! 🐾💦

Our incredible friends and community supporters at the SPCA of Anne Arundel County 🐶 are bringing back one of the absolute best dog-friendly events of the summer, and we couldn't be more excited to support them! 🎉

Mark your calendars for Sunday, August 23, 2026 📅 and get ready for a day of sandy paws, happy splashes, and community fun—all for a fantastic cause. 🌊🐕

🎈 WHAT’S IN STORE FOR YOU & YOUR PUP:
🏖️ Beach access for dogs to splash, swim, and play
🎶 Live music & beachy summer vibes
🍔 Delicious food & refreshing drinks
🛍️ Local vendors & awesome merchandise
🏆 Fun contests and activities for the whole family

❤️ THE BEST PART? 100% of the proceeds go directly to supporting the SPCA of Anne Arundel County and the animals in their care. 🐾 Your attendance helps provide shelter, medical care, and second chances for sweet animals waiting for their forever homes. 🏡✨

🎒 What to bring: Your four-legged best friend, beach chairs, blankets, and sunscreen! 🐕🦺🏖️☀️

More details on food vendors, sponsors, and entertainment are coming soon, so keep an eye out for updates. 📢 Let’s pack the beach and show our support for our local shelter animals! 🌊🐕

👇 Who is planning to go? Let us know in the comments! 👇

#PuppyPlunge2026 #SPCAAAC #AACSPCA #SupportLocalShelters #DogFriendlyMD #AnneArundelCounty #SaveTheDate

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Puppy Plunge Returns

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🌊 Save the Date: Puppy Plunge Returns August 23, 2026! 🐾 Summer may still be in full swing, but we already have one very important date for dog lovers to mark on their calendars! The SPCA of Ann...
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