The Story of Boston in Six Squares

As a city, they’ve long defined us. Now they show us how we’re changing.

Photographs by Bob O’Connor
Interviews by Joseph Mendolia

boston squares photo essay maverick square east boston

Photograph by Bob O’Connor

Boston is a city built around its squares, each one an ecosystem crackling with energy and life. We shop, work, and hang out in them every day. But if you’ve noticed that your nearest square doesn’t look, or even feel, the same as it used to, you’re not alone. From the luxury condos replacing more-modest homes near Maverick Square to the redevelopment of the Bolling building—a symbol of rebirth in Dudley Square—change is all around us, and our squares reflect the tension between Old Boston and New Boston more than anyplace else. Ahead, Bob O’Connor presents current snapshots of six ever-evolving squares, before they change forever.

Maverick Square, East Boston

(Pictured above.) This heavily working-class neighborhood is seeing a sudden spike in development, sending property prices through the roof. As many immigrant families get priced out (and others fight to stay), young professionals are flocking to the area, wooed by new construction and waterfront views.

boston squares photo essay dudley square roxbury

Photograph by Bob O’Connor

Dudley Square, Roxbury

Once a bustling city neighborhood, Dudley hit a long rough patch starting in the 1960s. Flash-forward five decades, and the area is entering a new era, symbolized by the sleek new Bruce C. Bolling Municipal Building: Incorporating the façade of the iconic Ferdinand, it now houses Boston Public Schools’ state-of-the-art headquarters. But what cost will this growth have for Dudley’s longtime residents?

boston squares photo essay dudley square roxbury guillermo ramirez cex

Photograph by Bob O’Connor

“[I like] how convenient everything is. Like, the bus station’s right there, you have a Walgreens right here. Everything is in a close area. There’s definitely been change: the Bolling building, the Tasty Burger. There’s a lot of litter around here sometimes. That’s probably the worst thing about it.” —Guillermo Ramírez, CeX employee

boston squares photo essay central square cambridge

Photograph by Toan Trinh

Central Square, Cambridge

At the MIT-adjacent borders of Central Square—a longtime arts and counterculture stronghold—residents are seeing the effects of the Cambridge tech boom, and the trendy cafés and soaring rents that come with it.

boston squares photo essay central square cambridge jack rollins cheapo records

Photograph by Bob O’Connor

“I work at the record store. Central Square is a wonderful place, because you don’t know who you’ll meet. It’s a hub. It’s very diverse. We got good art venues, we got good banks [laughs], good restaurants. I wouldn’t even begin to stereotype, because there’s so many different people.” —Jack Rollins, Cheapo Records employee

boston squares photo essay jackson square hyde square jamaica plain

Photograph by Bob O’Connor

Jackson Square/Hyde Square, Jamaica Plain

Boston’s Latin Quarter is getting a massive facelift thanks to a $250 million project that, when complete, will knit together J.P. and Roxbury with more than 400 housing units, a skating rink, and 60,000 square feet of retail space.

boston squares photo essay jackson square hyde square jamaica plain koga ninjazz rit it professional musician

Photograph by Bob O’Connor

“I work in IT at the animal hospital, and I do music at night. Eclectic stuff. I lived here over by Stony Brook years back. What’s nice about the area? All the Spanish food. The diversity of people. Education. We have a lot of young professionals out here. Things always change—that’s the only thing that remains the same.” —Koga “Ninjazz” Rit, IT professional and musician

boston squares photo essay union square somerville

Photograph by Bob O’Connor

Union Square, Somerville

With speculation about the Green Line Extension and real estate prospecting running rampant, a whole slew of hipster-friendly businesses have sprouted up among the neighborhood’s old-school bars and ethnic grocery stores.

boston squares photo essay kendall square cambridge

Photograph by Bob O’Connor

Kendall Square, Cambridge

Just call it Silicon Valley East: What started out as an industrial area more than 60 years ago is now the hub of tech innovation in Massachusetts. The only thing missing? A neighborhood feel. That could all change with MIT’s $1.2 billion plan for Kendall, which is slated to bring 740 apartments—not to mention additional office, retail, and research space—to the square.

boston squares photo essay kendall square cambridge rebecca rodriguez

Photograph by Bob O’Connor

“When I first moved here, there was nothing. There was just Au Bon Pain. And now there’s so many different restaurants, and it’s just full of really smart people who are really dynamic and interesting. It’s the best of both worlds. But there’s no grocery store. I’m dying to have a grocery store, or a CVS. Something.” —Rebecca Rodriguez, Kendall Square resident