Boston’s Biggest Food Challenges

Looking to feed your inner glutton this holiday season? Give one of these local food challenges a go.

boston food challenges

Photograph by Sarah Fisher

Unhinge thy jaw and stretch ye stomach, oh great gourmands of Boston. We’re prepping for the holiday season by biting off more than we can chew at the biggest, baddest eating challenges the region has to offer. Breakfast, lunch, dinner, and dessert, there are ample opportunities to pit your appetite against high-calorie concoctions designed to bust guts. Your tour guide: Oxford’s Geoffrey Esper, a rising star on the competitive-eating circuit who during our photo shoot was the very first person to complete La Famiglia Giorgio’s Meatballs and Sausage Challenge (nearly 3 pounds of pasta, eight meatballs, and six pieces of sausage). Hope you’re hungry.


Breakfast: Guinness Breakfast Challenge, Flann O’Brien’s


Photograph by Chris Garcia

The feast: Three rashers, four Irish sausages, three fried eggs, one pancake, six pieces of white and black pudding, a grilled tomato, mushrooms and veggies, home fries, Irish baked beans, white toast, buttered brown bread, a bowl of fresh chopped fruit, and an optional pint of Guinness.

Time limit: One hour

Cost: $23.95

Estimated Calories: 4,000

Difficulty: ★★

The reward: The meal (and dessert) are free, plus you get a $10 gift card, a T-shirt, and your name and photo on the website.


Lunch: Eagle’s Challenge, Eagles Deli and Restaurant


Photograph by Chris Garcia

The feast: Six pounds of hamburger patties topped with 24 pieces of bacon and 24 pieces of cheese, along with 5 pounds of French fries and a deli pickle.

Time limit: One hour

Cost: $65.99

Estimated Calories: 15,000

Difficulty: ★★★★★

The reward: The meal is free, plus you get a $100 gift card, a T-shirt, and your name on the wall.


Dinner: Lil Al’s Challenge, La Famiglia Giorgio’s


Photograph by Chris Garcia

The feast: Three pounds of homemade gnocchi mixed with four cut-up chicken cutlets and broccoli, all of it doused in pink vodka sauce.

Time limit: None, but it must be completed in one sitting.

Cost: $46.99

Estimated Calories: 13,000

Difficulty: ★★★★★

The reward: An “I ate the plate” T-shirt.


Dessert: Awful Awful Milkshake Challenge, Newport Creamery


Photograph by Sarah Fisher

The feast: Three 24-ounce milkshakes—you choose the flavors.

Time limit: None, but all three must be consumed in one sitting.

Cost: $13.89

Estimated Calories: 2,000

Difficulty: ★★★

The reward: A free fourth milkshake.

Esper’s Pro Tips

  1. Stretch your gut. Eat big on the days leading up to the feast. “Fasting for two or three days ahead of time is the worst thing you can do,” Esper says.
  2. Keep it nutritious until you can’t. Esper prefers training with gallons of water and pounds of raw veggies.
  3. Temper your ambitions. Learn your limits ahead of time. “A lot of people try to do a challenge and it’s just way too big,” Esper says.
  4. Stay cool. Avoid brain freeze from colder desserts by keeping the payload from rubbing the roof of your mouth.
  5. Eat what’s appetizing. “If you don’t like the food, it makes it a lot harder,” Esper says.