Man v. Food Season 1, Episode 5: Sleepy Hollow, NY

New York, NY

Casey Webb travels to New York City for the best in big city eats, including an insane challenge that has him choosing between a 151-ounce milkshake, an 8-pound sloppy joe or six habanero ghost chili wings.

Milwaukee, WI

Casey travels to Milwaukee for some epic Brew City eats, including a pitcher-sized Bloody Mary garnished with a whole chicken and a four-and-a-half-pound Reuben sandwich challenge.

Charleston, SC

Casey heads to Charleston, SC, for epic low country eats. He takes on the Belt Buster Challenge in which he must consume a two-pound burger, three pounds of nachos, an order of tater tots and a 12-ounce milkshake in 20 minutes.

New Orleans, LA

Casey heads to New Orleans to taste the best of the Big Easy, including a mammoth po' boy and a four-pound sundae packed with eight large scoops of ice cream and smothered with eight different toppings.

Houston, TX

Casey two-steps down to Houston, TX, for some Tex-Mex tastiness, including a colossal 22-ounce chicken-fried steak and the ultimate spicy challenge -- a burger topped with seven of the world's hottest chile peppers

Portland, OR

Casey heads to Portland, OR, to taste mouthwatering Peruvian chicken, a succulent porchetta sandwich and a two-pound burrito packed with ten of the spiciest peppers in the world.

Chicago, IL

Casey travels to Chicago for some epic Windy City eats, including a massive triple-threat pork sandwich and a challenge featuring a two-pound double bacon cheeseburger and two pounds of "Irish Nacho" cheese fries.

Des Moines, IA

Casey heads to Des Moines, IA, where he'll attempt the eat an overstuffed pulled pork sandwich slathered in a scorpion pepper hot sauce in ten minutes.

30 min

Bllings, MT

Casey travels to Billings, MT, to tackle a one-hour steak challenge featuring a 78-ounce rib eye and two pounds of mashed potatoes, salad and bread.