Jack’s Pumpkin Pop Up: A Fall Selfie Paradise

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Having experiences used to mean going out and doing things – watching a show, going to a dance, eating a meal, creating some art. Now, the concept of an “experience” has changed to mean…selfies. And lots of them.

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The backgrounds may change, but the activity is always the same; someone’s poor Instagram husband finding the perfect angle.

You won’t find many of these experiences featured on my blog because seeing 20 photos in a row of me just standing there smiling gets old.

That said, I’m not above occasionally indulging in these ridiculous, self-centered phenomena. Oh no, I stoop to embrace them! But by my standards, the experience must be high-quality, beautiful, and end with treats. Jack’s Pumpkin Pop Up in Chicago checked these boxes, so I dove in headfirst.

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My mom flew to Chicagoland to celebrate my birthday, and was kind enough to join me at Jack’s for a good, old-fashioned haunt jaunt, punctuated by increasingly spooky scenes of jack o’ lanterns and coffins, skeletons and pumpkin ghouls.

Thanks Mom for being my photographer for the evening!

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This incredible pumpkin house, wow!

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Do you like how I dressed like a pumpkin for the occasion?

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We enjoyed the mix of twinkling backgrounds and physical props to climb on, all harvest themed. Hay covering the ground set the mood considerably. I would have bailed right away if it felt like we were taking photos in a blacktop parking lot.

Get it, baled, like hay?

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This "sweater weather" background was made of real sweaters!

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Only five cents for a whole pumpkin? What a deal.

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Which one would you take home?

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How big was this pumpkin? See pumpkins for scale.

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I'm so tiny.

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Taking photos right before sunset resulted in the best portraits, but the thousands of lights strung around the pumpkin patch came alive after dark, as shown here at the gold mining sluice.

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As night drew near, so did the spookier side of the patch. We encountered haunting skeletons, the giant remnants of humans too large to imagine. I hid in this coffin, hoping it would not be my final resting place.

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Jack, the pumpkin king; the most ominous part of an otherwise tame Halloween experience.

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My mom and I made it out alive from the haunted corn maze to finish the night with some apple cider indulgences - cake donuts and a spicy spiked punch.

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Can you guess the artist behind the iconic style painted on this pumpkin? Why, it's Yayoi Kusama, of course!

We first encountered Yayoi's incredible art at the WNDR Museum in Chicago last winter. Her career as an exhibition artist began in her youth, inspired by visual and auditory hallucinations. The resulting artwork almost always incorporates polka dots, her signature, in inventive ways.

Click here to see our post about visiting the WNDR Museum.

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