10 Food Challenges + Over-the-Top Kalamazoo Foods to Try in 2025

10 Kalamazoo Food Challenges

Think you have what it takes to win a food challenge?

If you can eat these meals within the time allotted, you may win money, free food, or simply bragging rights.

We’ve found 10 food challenges in SWMI with super-sized meals.

Benny DiCarta’s menu is simple: three regular flavors (cheese, Italian sausage, pepperoni) and two monthly specials are offered in only one size: giant.

If your car or stomach isn’t large enough for a 28-inch pizza, Benny’s also sells by this unique food by the slice.

Food Challenge: Benny’s Challenge invites guests to finish a 28-inch pizza in less than 28 minutes. Reward includes a $280 check ($100 for professional challengers), Benny’s Challenge tee shirt (while supplies last) and your picture posted in the store.

This massive, unique food measures three feet long and includes beans, lettuce, tomato, onion, cheese, sour cream, and your meat or veggie choice in a grilled tortilla.

Food Challenge: For guests who can tackle the Don’t Even Think About It Burrito in less than 12 minutes, the meal is on the house, and you receive a free Big Burrito tee shirt.

Arlene’s Truck Stop in Battle Creek has several food challenges, most from its secret menu. Food challenge or not, this mom-and-pop style restaurant ensures you will never leave hungry.

Food challenge: These food challenges are meant to be fun and filling. Whether you finish or not, you may end up Facebook famous.

You’ll want to call ahead for this one — they need at least a couple of hours’ notice to prepare it.

The Mac Truck Burger (formerly dubbed the Dump Truck) includes 18oz fresh ground beef, 8oz ham steak, four fried eggs, four slices of cheese, four strips of bacon, and lettuce on a house-made 8-inch bun.

This monster-sized meal also includes a pound of fries and crispy pickle spear.

Breakfast is the most important meal of the day, so if you prefer a breakfast challenge, Arlene’s has you covered.

Challengers will attempt to finish a 22-ounce bun smothered in sausage gravy, cheese and bacon.

Many have tried, few have conquered.

This challenge meal lives up to it’s name and dares you to finish six eggs, bacon, ham, sausage, hashbrowns, half order of biscuits and gravy. And don’t forget three jumbo pancakes!

For those who prefer Mexican-style faire, Arlene’s wet burrito challenge is for you.

Take your shot on a 7-pound burrito with cheese, enchilada sauce, lettuce, onion, tomatoes and black olives.

The Hungry Boi Challenge at Lake Burger in Kalamazoo invites diners to try three, quarter-pound patties, American cheese and burger sauce stuffed between TWO grilled cheese sandwiches.

Food Challenge: This is a speed challenge. The participant must finish under the current standing record time to win.

Whether you finish this big meal or not, your picture goes up on the wall — either the wall of fame or shame!

The “Gutbuster” features three sandwiches combined into one 26-inch French loaf and paired with a pound of fries.

The three sandwiches include Italian beef, meatball and sausage links.

Food Challenge: If you can finish this meal in less than an hour, your meal is free, you can rename the challenge, and you’ll receive a free tee shirt. Your picture will also be added to the wall of fame.

Can you join the Wall of Flame? Finish 16 traditional wings in Wings Etc’s hottest sauce.

Food Challenge: If you can finish this meal without drinks, you will join the Wall of Flame and receive a t-shirt.

Maggie’s Viking breakfast includes four eggs any style, hash browns, four bacon slices, four sausage links, a slice of ham, and three pancakes with toast.

Food Challenge: Your photo joins the Viking wall if you finish this meal.

More Unique Kalamazoo Food

While eating these foods won’t earn you bragging rights, you may want to brag about how delicious (and sometimes enormous) some of these foods are in Kalamazoo.

A viral sensation in 2014, the Bear Claw Burger returned to Homer Stryker Field in 2025.

This burger serves two and includes a half-pound hamburger topped with smoked pulled pork, macaroni and cheese, and coleslaw between two bear claw donuts.

This meal is available at all Saturday home games and includes two bags of chips.

Even a pandemic didn’t stop this epic Bloody Mary Bar at The Dock at Bayview in Richland. When restaurants were closed to in-person dining, the team pivoted and sold them to go, in carryout kits.

Seemingly anything goes with this unique beverage; in addition to the traditional celery and olives, guests can add shrimp, chicken wings and cheese.

Also Try: Bloody Mary Bar at Louie’s Corner Bar or Louie’s Trophy House

While known for their extensive donut selection, don’t sleep on Sweetwater’s cinnamon roll. Easily eaten in multiple meals, this culinary creation will fill an entire dinner plate with its cinnamon sweetness.

Their cinnamon rolls are available glazed, with chocolate icing, vanilla icing, or caramel icing. You can also purchase them topped with peanuts.

If you’re looking for another large offering from their shop, order a fritter.

Also try: Rykse & Co cinnamon rolls

While nearly anything from Cherri’s Chocol’art is a decadent, unique food, their Monster Shakes have become a signature item in their shop. With different seasonal flavors, you can find a Monster Shake for any holiday or event.

The Halloween shakes pictured included the Caramel Apple Cider Monster Shake, Spooky Wooky Monster Shake and Pumpkin Pie Monster Shake.

Each shake features Lafayette Creamery’s ice cream and treats from the shop, which are made in-house.

Voted as one of the best restaurants in Kalamazoo for their burgers and chicken sandwiches, Nonla is also known for its innovative daily specials.

Whether it’s a fried pickle burger, steak and egg bagel or the Blueberry Bomber (shown), their kitchen creativity knows no bounds.

The Blueberry Bomber includes Belgian waffles, crispy fried chicken breast, jalapeño blueberry cream cheese, blueberry compote, bacon and powdered sugar served with maple syrup.

Follow their Facebook page for their latest creations.

Why scoop ice cream when you can roll it instead? Visitors will find this unique rolled ice cream accompanied by toppings like cookies, brownies or lemon bars.

Some of Rollup’s signature dishes include Monkey Business, Orange Dreamsicle and Sweet S’more (pictured).

The Sweet S’more includes a chocolate base, marshmallows, graham crackers, a chocolate bar, toasted marshmallows and whipped cream.

Did we miss one of your favorite Kalamazoo foods or food challenges?

Have we missed one of your favorite, unique foods in Southwest Michigan?

Leave us a comment and let us know!