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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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The week in Annapolis is PACKED and this is your heads-up so you don’t miss a thing 👀✨

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