View of Boston Skyline from the North End by Mike Richard
Boston, Massachusetts is arguably the most historic city in the United States. Philadelphia residents will argue this point to the death, but Bostonians politely thumb their collective nose as the “City of Brotherly Love”. The historical roads of the Declaration of Independence, Paul Revere’s Midnight Ride, the American Revolution, and the abolition of slavery all lead back to Beantown.
The city’s North End neighborhood, a.k.a. “Little Italy”, boasts more than 120 restaurants packed into just 0.36 square miles. It’s essentially ground zero for lovers of food in general and Italian food in particular. So what better way to explore the area’s history than a walking tour of Boston’s best pizzerias and historic taverns?
Meeting the Abominable Snowman in Boston’s North End by Mike Richard
We met our tour guide, Patrick, in the North End on a beautiful Saturday afternoon — one of those rare, fall New England days that feels more like the end of summer. For four hours, we visited three of Boston’s best pizzerias and two of the country’s most historic taverns. All the while, Patrick regaled us with countless tales of the city’s history, neatly woven between hot slices and raised pint glasses.
Regina Pizzeria in Boston’s North End Neighborhood by Mike Richard
We visited the city’s oldest, most iconic, and most famous pizzeria. Regina Pizzeria has served throngs of locals and tourists since 1926 and, on any given day, the line quite literally spills out into the street. Their famous brand of pie features a slightly chewy dough with a crispy crust, thin red sauce, and mounds of gooey cheese.
Ernesto’s is another old world favorite that’s been using the same recipe for more than three decades. It also offers the best selection of pizza by the slice. I chose to keep it simple with a slice of cheese that turned out to be my favorite of the tour. Be warned though: their “slices” are one-quarter of an extra large, 18-inch pie! Thanks to a constant stream of hungry patrons, the food never sits for long and their pies are always fresh and hot.
Isabelle’s Pizza at Fig’s by Todd English in Boston by Mike Richard
For a bit of contrast, we stopped at the more modern Figs by Todd English. While not technically a pizza joint, it offers a dozen creative takes on the typical sauce/cheese/dough recipe. We liked the Isabelle’s in particular – a unique, well-balanced, sweet and savory mix of sweet onion, country ham, aged provolone, and crispy asparagus. There’s plenty of local beers on tap and they have a decent, affordable wine list to boot.
As we strolled the streets of the North End neighborhood, it became clear that every step, every building, every park, reveals a fascinating history. Our tour was peppered with phrases like “George Washington used to drink here”, “this is where John Hancock’s brother lived”, and “this tavern is where the Colonists accidentally learned of the impending British invasion, prompting Paul Revere’s famed midnight ride”. These mini history lessons came so frequently throughout our tour that we couldn’t help but be dazzled by Boston’s past.
Patrick shared the latter phrase with us just before we ducked into the Green Dragon Tavern. While historical records can’t seem to agree, the tavern likely dates back to 1654 and still features many of its original architectural details. The modern day cover bands and 20-something’s who pack the bar at happy hour belie it’s rich, storied past. But there’s no denying that it’s literally the place that, among other things, sparked the American Revolution.
Historic Warren Tavern in Charlestown, Massachusetts by Mike Richard
Our favorite stop of the tour came just over the bridge in Charlestown. In an otherwise sleepy residential neighborhood dotted with cobblestone streets, small memorial parks, and centuries-old Colonial homes, it’s surprising to find one of the country’s oldest taverns. Established in 1780, Warren Tavern is a beer-loving historians dream. Rich wood accents, haphazard, 18th century architectural details, and original fixtures are all present today much as they were more than 225 years ago. Over pints of Harpoon and Sam Adams, Patrick confirmed that both George Washington and Paul Revere frequently tipped a few back within the tavern’s walls.
It’s impossible not to feel humbled, awed, and inspired there and everywhere throughout Boston. In the end, we raised our glasses to George and his comrades, in honor of their contributions to one of the greatest, most beautiful cities in America.
Exploring the Best Pizzerias and Historic Taverns of Boston’s North End from Boston Things to Do