The Pepperoni Heel: Columbia County Fair Legend and Hudson Valley Legacy

Super seasonal and micro regional, there’s one decadent handheld delicacy that defines the Columbia County Fair more than any other: The pepperoni heel. Available for only six days out of each year in Chatham, New York, the heel is a half a loaf of Italian bread stuffed with an extravagant amount of sliced pepperoni that’s been simmered until tender in tomato sauce, and served in foil with a purely decorative plastic fork. 

To the uninitiated, the description might sound downright unhinged. But for those who’ve had it, or grew up getting it at the Pierro’s Italian Sandwiches stand at every Columbia County Fair, it’s a work of art. It’s more peperoni than sauce, with just enough to keep things juicy. It’s spicy in a way that bites but doesn't linger, and the bread (made just for Pierro’s at a secret local bakery) is soft but robust enough not to soak through. The most surprising element of the heel, which makes it so craveable, is the texture of the pepperoni. Stewed down but still toothsome, the pepperoni take on the velvety softness of baby bunny ears. And each heel is seemingly stuffed with a thousand of them. 

Fourth Ward Hudson City Council member Rich Volo — AKA Trixie Star, Hudson’s preeminent drag queen ambassador and publisher of Trixie's List — knows a thing or two about heels, but never heard of the pepperoni varietal until after moving to Hudson in 2006. It was love at first bite for Volo, who grew up in an Italian family on Long Island. Now a vegetarian, he breaks his diet once a year, during fair season, just to get the pepperoni heel. 

“It’s about the indulgence,” says Volo. “The sheer amount of pepperoni is unbelievable.”

Nicholas, Chris, and Anthony Pierro

The paterfamilias of the Pierro pepperoni heel dynasty, and longtime Hudson politico, Carmine “Cappy” Pierro, has passed much of the work at the family fair stalls on to his sons, Christopher and Anthony, and nephew Nicholas. A couple of other stands at the fair offer pepperoni sandwiches, but Pierro’s, Cappy insists, was the original. 

The stand was started 70 years ago by Cappy’s father, Carmine Pierro Senior. He says he still remembers being four years old, watching his dad paint the first stand in the garage. The recipe hasn’t changed much since then. 

“The trick is you don’t overcook it,” Cappy says. “We have the ratio of pepperoni to sauce perfect.”

He adds that the only real change over the years is switching from deli-sliced pepperoni to pre-sliced Hormel. He says they use the brand because it’s the least greasy. Cappy recalls running into a Hormel representative at a Ginsberg’s Foods event once. The salesman had never heard of anything like a pepperoni heel and was amazed. The man asked for the recipe, to share with his company. Cappy declined. 

There are two Pierro booths, located at either end of the fairground. They also sells sausage and peppers, meatballs and chicken parm, but the pepperoni is always the star. The Pierros don’t serve food at any other events anymore, though they have been known to cook heels up every once in a while for a Hudson Fire Department fundraiser. 

“People will buy tickets to the fair just to get pepperoni. We’ve got a guy who comes every single day that the fair is open.” says Nicholas Pierro, the City of Hudson’s first assistant fire chief, working his booth by the grandstand, alongside his young son Jace. “I’m 40. I’ve been coming here since I was eight months old.”

Hudson History Takes a Heel Turn

An image on the side of the Pierro stall shows the original stand.

The pepperoni heel, it turns out, is more than just a Columbia County Fair icon. It, and stewed pepperoni in general, are also a significant artifact of Hudson cultural history. 

From 1922 to 1984, the Pierro’s Italian Grocery Store was a fixture at 243 Warren Street, started by Cappy’s grandfather. While the shop didn’t make pepperoni heels, it sold the spicy cured sausage to a number of local bars and restaurants that did. 

“It was pretty much a Hudson thing,” Cappy Pierro says. “My father sold it by the stick. He sold pepperoni to a lot of the bars and restaurants  Back in the day I’d get a pepperoni heel at Rocky’s, behind the Hudson Opera House (now Hudson Hall). I don’t know if they invented it but we still call the bread we use ‘Rocky Bread.’”

Interestingly, when Hudson Hall was installing an elevator in its rear, ten years ago, an old copper wire, dating back to the 1800s, and insulated inside tree trunks, was discovered in the wall. It was the remnant of a call system from a back chamber that rang a bell in Rocky’s nextdoor. Some say it was used to warn the bar when a show was letting out in the theater so they could prepare for a rush of customers. Others point out that the building was also used as City Hall, so it may have been a call button to have drinks, or maybe pepperoni heels, delivered to politicians.

Former seven-term Hudson mayor and current Fifth Ward county supervisor Richard Scalara (for whom Cappy served as mayor’s aide) says he still makes himself a pepperoni sandwich at home once or twice a month. Growing up in the city, cooked pepperoni was everywhere. He said it always surprised him when he couldn’t find Hudson’s staple ingredient anywhere else. 

“I used to go out of town and ask for a pepperoni sandwich and they looked at me like I had two heads,” he said. “One time in White Plains they served me sliced raw pepperoni with sauce on it. I paid and told them, ‘I thought I was hungry but I’m not.’”

Scalera also recalls one Hudson-cooked pepperoni dish from his high school days in the late 60s, which hasn’t survived the test of time (maybe for the better). 

“A late night snack bar called Johnny Wares served footlong hotdogs with pepperoni slices that sat in a pot for a week and came out by week’s end the size of nickels,” Scalara remembered. “Most people drank all night and topped it off with a ‘breath dog,’ as it was nicknamed… It was a challenge to keep it down.” 

Roots to the Old Country 

Pepperoni is believed to have been invented by Southern Italian immigrants in New York City in 1919. Accounts say it was an attempt to replicate something akin to soppressata, but without appropriate seasonings available in the U.S. they used paprika, which lends the sausage its distinctive red color. It’s unclear when pepperoni migrated up river but it was obviously a hit with Hudson’s large Italian community who, according to Cappy, were primarily from Southern Italy and Sicily. He confirmed that Hudson’s Italians also continued the practice of dipping bread in tomato sauce. 

Italian regional food expert, James Beard Award-winning cookbook author and Hudson resident Susan Simon says there is a clear culinary throughline between classic Italian traditions and the Pepperoni Heel. 

“The Italians say fare la scarpetta when you dip bread into sauce (which translates to) ‘make a shoe’  — so, it’s not so far fetched that the Hudson version of bread, sauce (and pepperoni) is made with the heel of bread.” Simon says. “The Sicilian tomato, herbs and olive oil bread is called pane cunzato. Which roughly translates from Sicilian dialect into Italian conciato — then into English as a ‘mess.’”

Simon marveled at how it all seemed to add up, adding that these simple dishes were primarily peasant food in the motherland. It wasn’t until Italians moved to America and began making a little money that they could afford to put meat in sauce. 

“This is how dishes are invented,” Simon continued. “People are nostalgic for something they had as a child and it evolves using what’s available.”

The current stage in the pepperoni heel’s evolution is a gut-busting masterpiece made mythical by its limited availability and a local lore as rich as the sloppy handful itself. A Hudson original and a Columbia County Fair legend, the pepperoni heel is a must try. But you’ll have to wait 'til next year.