The 8 Best Places for BIG Food in Connecticut!

If you have a big appetite or you simply love a challenge, Connecticut offers several spots with massive meals. From a 10-pound pizza to ultra-spicy hot dogs and an 8.5-pound sandwich, diners opting to take on these big foods better be ready. Will you defeat the food or will the challenge defeat you? Here are the best places for BIG food options in Connecticut! 

1. Randy’s Wooster St. Pizza Shop, Manchester, CT

How hungry are you? Are you hungry enough for a 10-pound stuffed pizza made from four pizza doughs and so many toppings they can’t be listed? To take on this challenge, you and a friend can eat “The Challenger” and see if you are hungry enough to beat the pizza… or will the pizza be too much for you?

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2. The Cheese Truck, New Haven, CT

This is the challenge for you if you love grilled cheese. The Cheese Truck is home to flavorful grilled cheese and a grilled cheese challenge, where you must eat 10 grilled cheese sandwiches with at least one topping in an hour or less. Winners can name their own sandwich, get their name on the truck, and are entitled to one sandwich per day for one year. Few have eaten their way through this cheesy challenge.

3. Leo’s Restaurants, Middlebury and Southbury, CT

Serving a wide range of typical breakfast foods, Leo’s Restaurant offers a challenge to diners seeking to take the notion “breakfast is the most important meal of the day” to the next level. Leo’s has a Kitchen Sink dish for a reasonable $16.99 piled high with French toast, pancakes, sausage, bacon, home fries, eggs, and fruit. A cup of coffee comes on the side to wash it all down, and those who beat the challenge receive a free t-shirt.

4. Famous Franks, Brooklyn, CT

The Frankenstein Challenge sounds as scary as it is. Those who are brave enough to take on this challenge can try to eat 24 hotdogs and three pounds of toppings piled onto an 18-inch grinder roll. If you can finish all this in 30 minutes or less, kudos to you… you’ll get your meal for free and receive a free t-shirt. So far only two people have beaten this challenge!

5. Mel’s Downtown Creamery, Pawcatuck, CT

If you are an ice cream lover, here’s one for you: The Big Kahuna Challenge. Dig into eight scoops of ice cream, seven toppings, one banana, and one brownie all topped with whipped cream and four cherries on top. If you manage to finish this one your own, you will win a gift card and a t-shirt.

6. Woody’s, Hartford, CT

Woody’s, known for their excellent hot dogs loved around the state, features the Devil Dog Challenge. This challenge consists of two-foot-long hot dogs topped with habanero mustard, ghost peppers, Trinidad scorpions, and Scotch bonnets—this is a very spicy challenge! Those who defeat this challenge must have finished every bite in 20 minutes or less without a drink or napkins. Winners get a t-shirt!

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7. Bear’s Smokehouse, Multiple locations

Home of delicious mac & cheese and Kansas-city style barbecue, Bear’s also offers ambitious diners a very difficult food challenge: the Bearwich. Prizes and bragging rights are the goal for someone who demolishes the entire Bearwich in 45 minutes or less. What’s in the Bearwich, you ask? It is a 1.5-pound roll packed with four pounds of brisket and pork, one pound of coleslaw, two pounds of mac & cheese, and all of it is topped with their signature sauce. Sound tempting?

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8. The Plum Tomato, Colchester, CT

If you eat a whole sandwich at the Plum Tomato in Colchester, you win a free t-shirt and bragging rights on their Facebook page. The sandwiches at the Plum Tomato are very delicious and most people take home leftovers, so this is a great challenge for beginner competitive eaters. Sandwich flavors rotate frequently, but you might find options such as the Big Buffalo, the Caesar Salami, and the Titanic Turkey.

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