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 eight-pound sloppy joe or six habanero ghost chili wings.

Casey Webb 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.

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

Casey Webb 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.

Casey Webb visits spooky Sleepy Hollow, New York, where he tries the massive Headless Horseman Burger and takes on the Dawg House Challenge in which a roll of the dice chooses 12 insanely topped hot dogs that he must eat in under 30 minutes.

Casey Webb two-steps down to Houston, Texas, 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.

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

Casey Webb 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.

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

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