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  • Cherish "5 Pounds" Brown

My Top 6 Favorite Ice Cream Challenges!

If You’re Susceptible to Brain Freeze, Proceed with Caution!


Hey, everyone - Cherish, here - and today I am bringing you a super chilling list of all of my FAVORITE ice cream challenges! It seems like food challenges are gaining popularity worldwide, and there really is a food challenge for everyone. There are burger challenges, pizza challenges, spicy challenges (my personal favorite), and of course, ice cream challenges (my second favorite), just to name a few.

So far in my journey as a competitive eater, I have attempted 8 ice cream challenges, with plenty more on the horizon, and I’ve compiled a list below of some of the most enjoyable ones. So zip up your coats and get some coffee ready because this is going to be an icy ride!


1. Pig Trough Challenge - The Barking Cow of Gaston


Ah, the Pig Trough Challenge at the Barking Cow of Gaston in Indiana. First on the list and also one of my first-ever fails - not to mention my very first ice cream win! (I got my redemption the following month.) This challenge consists of a layer of Oreo cookies, a super dense layer of soft serve ice cream, 5 big scoops of hand-dipped ice cream with your choice of flavors, a warm brownie, any syrup and candy topping of your choice, all topped off with whipped cream and a cherry. If you can finish this challenge in 30 minutes or less, you get the $14.00 sundae for free, your picture on the Wall of Fame, and a super cool Barking Cow T-Shirt! This is a great challenge for beginners and also ridiculously delicious.



2. Whole Hog Challenge - Skinny Kenny’s BBQ & Ice Cream


This challenge is not only delicious but also very cute in presentation, and with so many different textures to combine, it’s also a pretty easy one to get through! This was my second ever ice cream win, and it consists of 6 scoops of hard-packed ice cream (2 vanilla, 1 chocolate, and 3 other flavors of choice), Oreos, Pirouettes, whipped cream, hot fudge, nuts, and another topping of choice. This pay-to-play challenge costs $16.00 to try, and winners receive a free T-shirt and their picture on the Wall of Fame! If you ever find yourself in the Michigan area, definitely check this place out, even if only to try some of their mouth-watering barbecue.



3. Sundae Challenge - The Comfy Cow


This is one of the BIGGEST ice cream challenges I’ve completed so far, weighing in at over 6 pounds! The Comfy Cow has multiple locations in Louisville, Kentucky, with only a select few offering the challenge. (So make sure you call ahead if you’re in the area.) It consists of 15 scoops of ice cream, whipped cream, cherries, two different types of chopped nuts, and 4 additional “sidecars” of your choice. This one is a little on the expensive side, being a pay-to-play at $49.99, but winners do receive a plushie, a gift card, their picture on the Wall of Fame, and of course, a super cool T-shirt. I was so close to giving up during this challenge, but I’m so glad I pushed through and got that win!



4. Brooklyn Dump Challenge - The Swiss Swirl


This is a challenge that I did on a whim because I was just in the mood for a challenge that day. I can say with complete honesty that this is one of the best-tasting ice cream sundaes I’ve tasted in recent memory! Maybe it was because it was so much smaller than the usual ones I try, so I was actually able to enjoy it for once. The Brooklyn Dump Challenge located at the Swiss Swirl in Brooklyn, Michigan, is a jumbo sundae consisting of 32 ounces of your choice of ice cream flavors, topped with chocolate syrup, caramel, butterscotch, marshmallow sauce, peanut butter, M&M’s, Reese’s Pieces, Oreo’s, Whoppers, and Butterfinger pieces. (And of course, whipped cream and a cherry.) It costs $9.25 to try, and it must be completed in a one-sitting time limit to win, with winners getting their name on the Chalkboard Wall of Fame!



This challenge was located in such a cool and unique place in Marshall, Michigan, that it’s worth it just to go walk around their convenience store and buy some gourmet popcorn while you’re at it! It consists of 15 scoops of ice cream with your choice of flavors, plus 5 toppings of your choice, and it must be finished in 15 minutes or less to receive the $20.00 meal for free and your name and time on the Wall of Fame.


6. Kitchen Sink Challenge - Colonial Cafe


Last but certainly not least is the World Famous Kitchen Sink Sundae challenge, located in Naperville, Illinois. Unique not only in name but in presentation, this challenge consists of two whole bananas, six scoops of vanilla, chocolate, and strawberry ice cream, toppings of chocolate, pineapple, and strawberries, all covered in whipped cream, toasted almonds, and a cherry. This is a pay-to-play costing $17.99 with a one-sitting time limit, and winners will receive a free bumper sticker claiming that they ate the “whole kitchen sink!” (And if you’re Cody Dulaney, you might even get to take the sink home with you.)


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