Everyone loves a challenge, right? Well, here in Boston, there are several restaurants that dish out meals not meant for consumption by a normal human being. Gut-busting burgers, mouth-scorching wings, and heart-attack-inducing hot dog challenges are just the beginning. Check out our list of best food challenges in Boston. And if you’re daring enough, feel free to try one of them. Also, if you live to tell about it, let us know in the comments section below.

(Photo Credit: Eagle’s Deli)

Challenge: The Eagle Challenge is 5 lbs of burger, 20 pieces of bacon, 20 pieces of American cheese, 5 lbs of fries, 1 deli pickle, and a fountain soda.

Cost: $59.99*

Prize: Your money back + $100, a T-Shirt and bragging rights.

According to Eagle’s Deli, no one ever has ever ever beaten this challenge… ever! If you dig deep on the internet, you’ll find two instances of people claiming to have conquered this monster. But, since you can’t believe everything you read on the internet, we’re going with Eagle’s Deli version of the story. Good luck.

(Photo Credit: Spike’s Junkyard Dogs)

Visit website to see other locations

Challenge: Devour 6+ hot dogs

Cost: $3 per dog x 6 = $18*

Prize: A t-shirt and a spot on the Wall of Fame.

We know what you’re thinking: Six hot dogs? Piece of cake. But not so fast. These oversized all-beef dogs are stuffed into what is basically the equivalent of a sub roll. A fantastic selection of toppings makes the challenge taste better, but we doubt it will help much when it comes to actually finishing.

(Photo Credit: Andre’s Cafe)

Challenge: Andre’s 5+1 Rollup: Eat any 5 Specialty Roll-Ups & Fries within 45 minutes.

Cost: $7 per sandwich range x 5 = $35*

Prize: The meal is free. Your next meal is free, and you get your photo on the Wall of Fame.

The same Andre’s Café that boasts “delicious healthy food served fast” on its website offers up a challenge where you gluttonously eat 5 delicious and healthy wraps in one 45 minute sitting. We call that quality AND quantity. Andre’s came up with the idea for the 5+1 challenge after the 2+1, 3+1, and 4+1 challenges had all been defeated. With that said, if you beat this challenge, we’re guessing you’ll also get the satisfaction of being responsible for an even more difficult for future competitors.

(Photo Credit: Mass Ave Tavern)

Challenge: Uncle Buck’s Flapjack Challenge – A six-pound stack of flapjacks.
Cost: $19*

Prize: The pancakes are free, you get a sweet hat, and your name goes on the Wall of Fame.

When: Saturday and Sunday Only: 11:30 a.m. – 4 p.m.

On Saturdays and Sundays, Mass Ave Tavern serves up a huge stack of pancakes with a side of nostalgia. The title of their challenge cleverly references the pancake scene in the ’80s classic Uncle Buck with John Candy. If you’re thinking about this one, let me just say, “I hope you’re hungry.”

(Photo Credit: Sal’s Pizza)

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Challenge: Eat an entire 19”, 3lb. Cheese Pizza in 9 minutes or less.

Cost: $10.99*

Prize:Your next Cheese Pizza is free. You also get your picture on the Wall of Fame!

Roughly 3 billion pizzas are sold in the U.S. each year. And while could find absolutely no statistical information to back up the following made-up number, we estimate that college students are responsible for approximately 80 percent of those sales. Since Sal’s Pizza sits dangerously close the Boston University campus, and we’ve established that college students eat a lot of pizza, we assume this challenge is extremely difficult to conquer – otherwise, Sal’s would end up going bankrupt.

(Photo Credit: Vito’s Tavern)

Challenge: Eat 10 Atomic Wings

Cost: $9.99*

Prize:The wings are free if you eat them all.

Tucked away in the menu at Vito’s Tavern in Boston’s North End is a note that reads “on the house if you eat them all. You won’t.” The note refers to Vito’s Atomic Wings, which are coated in Habenero and Ghost Chile sauce. They’re hot – really hot.

Side note: Check out a couple of other spicy challenges we left off the list: Hell Week at East Coast Grill and the Ghost Chili Margarita Challenge at Rattlesnake Bar and Grill.

(Photo Credit: La Famiglia Giorgio)

Challenge: Misto Di Pesce: Eat a pile of Clams, Mussels, Calamari and Shrimp Over Two Pounds of Pasta.
Cost: $45.95

Prize: T-Shirt that says ‘I finished the plate’.

Massachusetts is certainly known for its fantastic, fresh seafood, so why not pack as much as you possibly can into one bowl and serve it over a ridiculous amount of pasta? Somehow, we don’t see this one ending very well. But take note if you’re lacking in confidence, La Famiglia Giorno’s site says “few have succeeded,” meaning other people have been able to take down this challenge.

* Challenge costs are estimated and do not include any medical expenses you may incur as a result of trying them.

Comments (4)
  1. dan says:

    and they want people to lose weight

  2. My mouth dropped when I saw the first pic. I am a fan of Regina’s salami and onion pizza. It’s not on the menu, but you can order it …it’s delish!