What I Learned Searching for Boston’s Best Pizza

In a town known for seafood, cream pies, baked beans, and basically anything other than ’za, our food editor set out to discover the best slice in the city. But as he tasted and tested, he learned a helluva lot more about Boston than he bargained for.

Photo by Nina Gallant

I’m not sure how to pick the best pizza in Boston.

I know I shouldn’t be saying that. I’m the food editor of the magazine you hold in your hands, for Chrissake—no time for self-doubt now. But when my bosses tasked me with taking a journey to find the single best slice in Boston, I gulped—and hard. The stakes were high. Pizza, after all, is universally beloved. It is the Beyoncé of foodstuffs: You either like it, in one capacity or another, or you are lying.

It also comes in many different forms; everyone has a distinct idea—sometimes several—of what pizza is. Growing up in a small town about an hour southwest of Boston, pizza for me was the homemade Sicilian-style squares my grandmother left in a pan on the kitchen counter during Sunday visits. It was also my homemaker mother’s reliable too-tired-to-cook meal—although she always tenderly topped the frozen Ellio’s pie with olive oil, garlic powder, and mounds of extra shredded cheese. Pizza from Greek-style parlors, meanwhile, was the go-to grub for every birthday party in the ’burbs.

Since then, I’ve eaten pizza in Rome, pizza in New York, pizza in the North End. As a professional diner, I’ve relished gourmet slices with deeply flavored, smoky tomato sauce; unctuous fresh mozzarella; and heavenly bites of yeasty dough that yield to a crisp crust. As a creature of habit, I’ve been ordering the same Friday-night takeout pie topped with Buffalo chicken—two sides of blue-cheese dip—from a Brighton hole in the wall for 15 years. (The heart, alas, wants what it wants.)

All of which raises the question: How do you choose the best of a category that has so many different interpretations? And what’s the unit of measurement on this yardstick? Are we talking about technical skill, emotional experience, fidelity to a tradition—or some combination of the three? Already, the task seemed impossible. And it was made even more so by the fact that, philosophical considerations aside, Boston doesn’t exactly have the strongest pizza identity.

Think about it. Everyone knows what New York– and Chicago-style pizza is. Detroit (thick, pan-baked slabs with tangy brick cheese) and St. Louis (cracker-like pies with processed Provel) have clear calling cards, too. But has our city spawned a distinctive, similarly famous “Boston style”?

The short answer is not really. Sure, we have the aforementioned Greek-style slices, brushed with faintly sweet sauce and baked in electric ovens in shallow, well-oiled pans that nearly fry the crust. There’s also the South Shore’s so-called bar pizza—tavern-proffered pies that are well done, a bit more than wafer-thin, and covered in char-spotted cheese (mozzarella cut with cheddar) that oozes all the way to the edge. But like candlepin bowling, the popularity of these styles is limited mostly to New England. Proud culinary exports, they are not.

Rather, Boston has proven much better at importing pizza. Want great coal-fired slices? We’ve got ’em, courtesy of spots like Max and Leo’s and Frank Pepe Pizzeria Napoletana, whose iconic original location in New Haven, Connecticut, made the style synonymous with that city. In 2010, Somerville’s Posto became New England’s first restaurant officially certified by the Associazione Verace Pizza Napoletana, a Naples-based trade organization that controls the designation of Neapolitan pizzas based on specific ingredients and cooking style. And Somerville’s Avenue Kitchen + Bar, as well as Volo Craft Pizza in Swampscott, offer locally rare Detroit-style pizza, which emerged in the 1940s when one Motor City tavern started baking pies (built cheese first, sauce second) in repurposed steel pans from automotive factories.

In fact, the more I’ve thought about it—and the more slices I’ve scarfed down—the more I’ve come to realize that this city’s approach to pizza is a perfect metaphor for Boston as a whole: We’re one of America’s first melting pots, after all, and, with our deep-rooted university culture, still a city where people come from all over the world to share ideas. So it makes perfect sense that, pizza-wise, we have a little bit of everything.

At the same time, we’re also a city of revolutionaries and innovators at heart: Enter a wave of next-gen pie artists who are using our diverse slice-scape as an excuse to experiment with different combinations of crusts, ovens, and toppings to create pizzas that don’t fit neatly in any one box. And just as rapidly developing Boston is shading its local color with more-cosmopolitan hues, the humble pizza is increasingly receiving elevated makeovers from hot-shot chefs with fine-dining backgrounds. Take, as just one example, Bronwyn chef Tim Wiechmann, formerly of the elegant French restaurant T.W. Food: His new T & B Pizza features Roman-style al taglio pizzas cut into thick squares with scissors, as is rustic tradition, but topped with fancy fixings such as tuna crudo and raclette cheese (and served alongside a cool craft-cocktail program).

All of which is to say: If Boston still lacks a single so-called style, we’re nonetheless gaining traction as a really great pizza city. “A few years ago, nobody was talking about Boston pizza,” says Raffaele Scalzi, cofounder of July’s third-annual Boston Pizza Festival, which brings about 15,000 attendees to City Hall Plaza and bills itself as the largest pizza fest of its kind in the country. “Now they are.”

But back to the question at hand. How do you judge the best pizza in Boston? It hits me as I’m inhaling an epic feta-and-pepperoni-topped pie from Somerville’s buzzy Hot Box, one of a few operations giving the South Shore bar pie a new, cheffed-up lease on life: Forget traditions and taxonomies. When hunting for Boston’s best pizza, there’s only one question worth asking: “Is this delicious?”

I’m ready to find some answers.

In searching for Boston’s best slice, it made sense to start where it all began. It’d been a while since I’d hunkered down in a cozy corner booth at Regina Pizzeria in the North End, where the walls are crammed full of framed, autographed photos of all the celebrities who have visited Boston’s oldest pizzeria since its founding in 1926. When your job requires keeping up with what’s new, decades-spanning standbys can be easy to neglect—but I wanted to find out if Regina still stacked up.

Spoiler alert: It does. The simple cheese pizza remains classic and craveable, which explains why, even on a wet and gloomy Friday afternoon, a line of mostly tourists is patiently taking shelter from the rain under Regina’s red awning. It also explains why, even as Boston’s pizza scene grows, many chefs tell me the original Regina—not, they stress, the chain’s inferior other locations—still offers some of the city’s finest. Every slice—toasted by the 900-degree flames of a gas-fired sand-and-brick oven—remains pliant enough to fold and still carries a pleasantly bready aroma.

“It’s all about the dough,” confirms co-owner Anthony Buccieri when I sit down with him to learn more about the business. Buccieri, whose family has run the restaurant since buying it from founder Luigi D’Auria in 1946, is a comforting composite of characters in my extended Italian-American family: warm and familiar, with a big, bushy mustache; an absence of “r” consonants in his vocabulary; and a cloud of cologne dense enough to overwhelm the most pungent garlic. And he’s about to give me a lesson about the history of pizza-making in the Hub.

As in other early urban centers across America, Buccieri explains, Boston’s first pizza shops were born out of Italian bakeries run by immigrants who transformed flour, water, and a handful of other bulk ingredients into various breads and pastries that were easy to make (and sell) en masse. Pans of pizza were typically the byproduct of the day’s leftover dough, a way to make use of what would otherwise be wasted. Often, the pizzas proved so popular, they eventually eclipsed the cookies and cannoli.

Buccieri believes the Regina building was a bakery before D’Auria started using its oven exclusively for pizza. Nearby Parziale’s Bakery, opened in 1907, boldly claims to have introduced pizza to New England. Over in East Boston, the family-owned pizza icon Santarpio’s started its life as a bakery: Since then, the well-done pizzas—unusually built with the toppings first—legendarily surly scene, and stridently no-frills vibe have earned it both city-legend status and national acclaim from Food & Wine.

Then there’s Galleria Umberto, a North End maker of arancini, calzone, and, most famously, pizza that began as a 1960s bakery. Last year, the spare and humble counter-service spot received a special America’s Classics award from the James Beard Foundation, reserved for restaurants that are “beloved” for “quality food that reflects the character of their communities.” The Beard medal hangs high on a wall at Umberto, though owner Paul Deuterio, whose father launched the spot, seems modest and unmoved when I ask him about it. (“Many people said, ‘Ooh, that’s like joining the big leagues,’” he says with a shrug.) After all, this is not a fancy place—thick, cheesy pads of Sicilian-style, pastry-oven pizzas are tossed onto paper plates or boxed up in string-tied white boxes. They fly out the door at $1.85 a slice, and when the day’s stock sells out—usually around 2:30 p.m.—they simply shut the doors.

The cafeteria-like space may not look like much, yet I wonder if I’ve found a winner as I chomp into an Umberto slice while a staffer flips the door sign to “Closed” and starts sweeping up around me. With its fleshy dough and wonderfully browned, leopard-spotted layer of cheese, it tastes to me like hearty home cooking, rivaled only by the similar squares I’ve already devoured in the burnt-orange plastic booths of Armando’s Pizza in Cambridge, an old-school, takeout-friendly parlor with its own storied rep. At this point, I remind myself to be careful: Consciously or not, I’m probably partial toward the kind of Sicilian-style pizza (thanks, Grandmas Rose and Josie) that introduced me to the ultimate comfort food in the first place.

Then again, when it comes to pizza, everyone has a bias. In fact, as I chat with local chefs about Boston’s pizza scene—from how we rank among cities to where they find their favorite slice— a consensus emerges: The pizza you grew up with is the pizza you love the most. But what does this mean for Bostonians, who grew up with so many different styles and whose city has historically been sniffed at (at least among pizza nerds) for lacking the strong, singular identity associated with other cities?

It means we get to make our own.

Take star chef Tiffani Faison. This fall, the Beard-nominated Top Chef alum will open Tenderoni’s at High Street Place, a multivendor food hall downtown. But rather than romanticize eons-old pie-making traditions, Faison just wants to create awesome pizzas that satisfy a certain kind of emotional hunger—in her case, for 1980s-style hometown parlors where taste and tone, rather than slavish devotion to technique, was the point. “If South Shore bar pizza and Detroit-style pizza and Pizza Hut had a baby,” she explains, “that’s somewhere in the neighborhood of what we’re aiming for.”

From crust to oven, Old World styles require strict adherence to tradition. Faison, by contrast, will operate her pizza joint with only one mandate: “No rules.” And she’s not the only one.

It’s 10:45 a.m. on a gloomy, gray May day, and I’m about to grab an early lunch at Stoked Wood Fired Pizza Co. Founders Scott Riebling and Toirm Miller have already parked their 3,800-pound, wood-fired pizza oven in Dewey Square in the heart of downtown Boston. The crust-crisping behemoth is built into a food truck—it’s one of the few setups like this in the country—with a 20-by-8-foot kitchen that serves as many as 300 personal-size Stoked pizzas to hungry office workers and tourists during a typical shift. They sling even more at their Brookline brick-and-mortar restaurant, which opened in 2016.

Riebling, a prolific music producer and former founding bassist of the Boston-born alternative-rock band Letters to Cleo, started making pizzas as post-show snacks while touring, during which time he studied pizza cultures in different cities. He later traveled to Naples for research, and even rewired his home oven to cook while on scorching “clean” mode in an effort to properly perfect his experiments.

Rock ’n’ roll is about breaking the rules, so it makes sense that Riebling’s pizzas aren’t concerned with fidelity to any one regional form. “We’re our own thing. That’s what I think the future of pizza is,” Riebling says. Though wood-fired like Neapolitans, Stoked’s crusts are cooked more well done (closer to New Haven–style) and topped with nouveau fixings such as spicy-chili-infused honey and Impossible Burger. Riebling admits that when he and Miller launched the truck, pizza-purist friends scoffed. But five years later, he adds, “People have started to accept that pizza is either good or it’s not.”

That checks out. When I reflect on the pizzas that have been making me dream of seconds and thirds lately, what they share is unbridled enthusiasm and a sense of fun, not an air of authenticity. I’m thinking of Stoked’s funky, wood-fired rounds and Hot Box’s electric-oven-cooked bar pies, dressed up with dill pickles and ghost-pepper-infused cheese and dispensed from a window in a hipster-filled retail courtyard. The flavorfully charred, rustic-American offerings of Area Four and Brewer’s Fork, designed to pair perfectly with their respective restaurants’ super-cool craft-beer lists. And the style-free “squares” and “rounds” on the menu at Rabottini’s Pizza, a buzzed-about pop-up project from chef Dan Roberts, who perfected his not-quite-categorizable pies at Portland, Oregon’s acclaimed Apizza Scholls under owner Brian Spangler, an artisan bread baker. “You can call it whatever you want. It doesn’t matter to me at all,” explains Roberts of his pizza. “What I promise is that it will be delicious and have integrity.”

All of this navel-gazing with pizzaiolos is well and good, but I’m no closer to finishing my find-the-best assignment when I wander into Dragon Pizza in Somerville. The spot has been getting buzz since last year, when chefs Charlie Redd, Keenan Langlois, and Antonio Reyes flipped a Davis Square address that formerly belonged to just another unexceptional city slice shop. Now the “punk-rock pizza shop,” as Redd refers to it, is decked out with funky pendant lights, cassette mix tapes hanging on the wall, and a framed photo of Road House–era Patrick Swayze. The restaurant’s name is handwritten on takeout boxes in graffiti-like strokes of neon paint.

As for what’s inside those boxes? Pies that clearly show a passion for the art of pizza-making without being too precious for a Tuesday-night snack. Toppings are top-notch and cover every craving: There’s the ruddy spice of house-made red-wine-and-garlic sausage. The sweet-and-salty dialogue between bacon and drizzles of chili-spiked maple syrup sourced from a sugar shack in the Adirondacks. Even citrus accents to balance the richness in Dragon’s lemon-chicken pizza, a nod to the signature dish at the late, great Hamersley’s Bistro, where Redd was once a line cook.

Later, Redd shares with me some of the other inspirations for Dragon’s pies: biting into a slice at Santarpio’s; his travels in Italy; Langlois’s deep-dive research into New York City shops. As with the rest of the city’s most delicious pies right now, this is an approach that celebrates Boston’s ability to combine multiple worlds, multiple perspectives, and multiple histories into something all its own. No one’s coming here for a taste of the Big Apple, Chicago, or anywhere else.

What they are coming for? You guessed it: the Best of Boston.