Your Guide to the Weird (and Wonderful) Alleys of Boston’s North End

Duck down any one of these, cannoli in hand, to explore the city's oldest neighborhood.

Photo of All Saints Way by Alice Brown

Boston’s North End has very little grass but nearly 40 alleys, as well as a dozen paved parks and plazas, all packed into 0.13 square miles in the little wedge of a neighborhood between Atlantic Avenue and Commercial Street to the east and I-93 to the west. Sure, you’ve been there for a late night cannoli or followed the red brick line of the Freedom Trail—but have you explored its many quirky alleyways?

Exploring some of the North End alleys allows you to appreciate the tiny details, from the architecture to the Italian residents who still live and go to Mass there. Even though the neighborhood is usually crawling with tourists, the alleys are typically quiet and calm.

Photo by Alice Brown

Most of the streets are narrow in this neighborhood (it wasn’t exactly laid out with large motor vehicles in mind), but you can appreciate just how narrow some of them are by stopping by North Square and checking out the public art there, which includes a bronze map of the neighborhood by Ann Hirsch and Jeremy Angier.

Public Alley 101

Numbered like an introductory course and labeled clearly, Public Alley 101 is a great place to start your tour, whether you’re beginning from Quincy Market, Christopher Columbus Park, or the Rose Kennedy Greenway. The alley is chained off to prevent cars from driving between Cross and Richmond Streets, but you can stroll down this cozy block with its picturesque gas lamps. In the summer, residents typically put out potted plants, but there’s noticeably less green in the winter.

Powers Court

Entering off of North Street, Powers Court has a sign that reads “public footway.” It’s a very reassuring sign, because the narrow passage is overhung with fire escapes and it looks like a dead end, but it makes a sharp turn to the left to connect with skinny Hannover Avenue. Look for plastic flowers in the window and a plaque that could have come from an ancient Mediterranean civilization. Or turn to look back at the entrance to check out the grand eagle perched on the Lincoln Wharf facade.

Board Alley/Bricco Place

Just off the bustling chaos of Hanover Street is the most delicious dead end in the neighborhood. Though officially known as “Board Alley,” there are half a dozen Bricco signs that will confirm you’re heading in the right direction. The terminus of the alley is home to the Bricco Panetteria (a bakery down a narrow staircase), Bricco Salumeria (selling meats, pasta, olives, and sandwiches), and Bricco Suites (a tiny extended stay luxury hotel). In the summer, you can pause to enjoy your treats at the picnic tables wedged into the postage-stamp-sized courtyard as the smell of fresh bread wafts round you.

All Saints Way

There are hundreds of saints depicted on plaques and cards inside the gates of All Saints Way off of Battery Street. Though the gates are usually locked, it’s heavily decorated from the outside so you can’t miss it–look for Christmas decorations in winter and gorgeous geraniums in the summer. It’s been curated for many decades by Peter, a resident in his 70s who will tell you that he grew up in the neighborhood with a Sicilian mother, a Roman father, and a love of St. Anthony. If he’s around, he’ll happily open the gates and show you inside as he entertains you with stories of visitors from around the world and peppers you with questions about your childhood and religious upbringing.

Greenough Lane

The entrance to Greenough Lane from Commercial Street doesn’t look particularly inviting; the pavement is spray painted with utility markings, and it’s not clear what’s waiting around the bend. But the lane rewards the bold explorer when the asphalt becomes cobblestones, the fire escapes become balconies, and it opens onto the verdant Charter Street Park, one of the only places in the neighborhood where one would be tempted to use the word “lush.” Even the street lamps here are elaborate and elegant.

Lombard Place 

If you’ve made your way to Bova’s, the 24-hour bakery and sandwich shop at the corner of Salem and Prince Streets, continue down Prince with your cookies to visit Lombard Place, also known as Leonard J. “Leo” Rizzuto Place in honor of a local resident who passed away in 2015. The alley curves around to Thatcher Street, creating a shortcut (by seconds) to Pizzeria Regina. The most charming thing about this alley is the row of potted herbs growing from repurposed Folgers containers. You’ll also find a quirky window covering that looks like a view of the sea from an arched terrace.

Cleveland Place

In a city where everyone seems to need a parking space directly in front of their house, there are an incredible number of entrances to apartment buildings pouring off of Cleveland Place despite it being only for pedestrians. Though move-ins are probably a hassle and the walk up either Margaret Street or Snow Hill Street is steep, there’s a nice view looking north with a glimpse of Lovejoy Wharf and the CONVERSE star perched atop the refurbished historic warehouse.

Jackson Avenue

Calling this an avenue feels like a bit of a reach for these public stairs, but there are several very nice homes along it. One of those is the Ozias Goodwin House, built in the Federal style in 1795 and added to the National Register of Historic Places 193 years later. The upper floors of the Jackson Avenue buildings have a commanding view of Charlestown and the USS Constitution. You can get a pretty good view from Copps Hill Terrace where an abundance of benches also allows you to get off your feet and admire Langone and Puopolo Parks.