11 Food Challenges + Over-the-Top Kalamazoo Foods to Try in 2024

arlenes food challenge wet burrito food challenges in Michigan

cover image: Arlene’s Truck Stop

Go Big, Because You’re Home: Food Challenges + Unique Food in Kalamazoo

Kalamazoo is a foodie town, offering cuisine for every taste bud: sushi, tacos, ice cream and burgers are all here in spades.

But what if you want something a bit outside of the norm: food challenges that reward you with free food if you finish it by yourself? A tee-shirt to commemorate finishing said food? Plain ol’ bragging rights?

Yup, we have those too. We scoured the best restaurants in Kalamazoo for what we’ll term “over the top” or unique food in SWMI.

Our thanks to the restaurants for their innovative culinary skills and fantastic photos.

Monster shakes at Cherri’s Chocol’art are some of our favorite over-the-top Kalamazoo foods.

11 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 11 food challenges in SWMI with super-sized meals.

Note: Food challenges are subject to change without notice. Be sure to call ahead to confirm challenge availability, prizes and rules.

These meals often require advanced notice for the kitchen to prepare and are dine-in only.

28-Inch Pizza Benny’s Challenge

Benny DiCarta’s
232 E Michigan Ave Kalamazoo, MI 49007
Price: $40

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.

Don’t Even Think About It Burrito Challenge

The Big Burrito Mexican Restaurant
5036 W KL Ave Kalamazoo, MI 49009
Price: $35.99

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 Food Challenges

Arlene’s Truck Stop
4647 Columbia Ave W Battle Creek, MI 49015

Arlene’s Truck Stop in Battle Creek has several food challenges, most from their 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 just end up Facebook famous.

Mac Truck Burger Challenge

Price: $45.00

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.

Loaded Biscuits and Gravy

Price: $30.00

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.

The Freightliner

Price: $35.00

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!

The Big Wet Burrito

Price: $25.00

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.

Hungry Boi Challenge

Lake Burger
4404 West Main St Kalamazoo, MI 49009
Price: $20.00

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!

Ray Ray’s Gutbuster Challenge

Ray Rays Italian Beef & Sausage
1715 Miller Rd Kalamazoo, MI 49001
Price: $50.00

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.

Viking Breakfast Challenge

Maggie’s Café & Catering
3290 Stadium Dr, Kalamazoo, MI 49008
Price: $15.75

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

Food Challenge: If you finish this meal, your photo joins the Viking wall.

Whole Hog Ice Cream Challenge

Skinny Kenny’s BBQ & Ice Cream
7000 Stadium Dr Kalamazoo, MI 49009
Price: $15.25

Order the “Whole Hog” at Skinny Kenny’s BBQ & Ice Cream and you’ll be treated to two scoops of vanilla ice cream, one scoop of chocolate ice cream and three scoops of your choice of ice cream.

The dessert also includes Oreos, pirouettes, whipped cream, hot fudge, nuts, and one additional topping (your choice).

Food Challenge: If you finish this dessert in under 15 minutes, you’ll receive a free tee shirt and your photo on the restaurant’s wall of fame.

food challenge, Skinny Kenny's BBQ, best ice cream

The Breakfast Challenge at Long Island Cafe

Long Island Cafe
5222 Portage Rd, Portage MI 49002
Price: $40.00

Originally named the Nathan Klein Eats Breakfast Challenge, it was renamed Ambers Breakfast Challenge in 2024 by the new champion, Eli Lessig, who finished in record time — just 19 minutes and 55 seconds! 😮

The breakfast challenge includes the cafe’s signature breakfast items: a double Tsunami Omelette, a double portion of potatoes, two cinnamon roll pancakes, a slice of toast, and one glass of water or soda.

Food Challenge: If you finish within 60 minutes, you’ll receive the meal for free, a tee shirt, and a place in Long Island Cafe’s hall of fame. Beat the record time and the challenge will even be named after you.

More Unique Kalamazoo Food

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

Bloody Mary Bar

The Dock at Bayview
12504 E D Ave Richland, MI 49083
Price: $20.00

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

Dinner Plate Sized Cinnamon Rolls

Sweetwater’s Donut Mill
3333 Stadium Dr Kalamazoo, MI 49008
2138 Sprinkle Rd Kalamazoo, MI 49001
2807 Capital Ave Battle Creek, MI 49015
Price: $3.49 and up

While known for their extensive donut selection, don’t sleep on the 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

Monster Shakes

Cherri’s Chocol’art
101 S Kalamazoo Mall Kalamazoo, MI 49007
Price: $12.25

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 flavors seasonally, 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, made in-house.

Nonla Burger’s Daily Specials

Nonla Burger
2103 S Burdick St Kalamazoo, MI 49001
1700 South Drake Rd Ste A Kalamazoo, MI 49006
24050 Front St Mattawan, MI 49071

Price: $5 and up

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.

Rollup Ice Cream

Rollup Ice Cream & Tea
5907 Gull Rd Kalamazoo, MI 49048
Price: $7.10

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!

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