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One man’s quest to photograph, paint, and preserve Boston’s historic buildings

From Charlestown to Roxbury, Matthew Dickey, known as the “Streetscape Curator,” scouts out hidden gems on his bike — then gets to the bottom of their history.

Taking a ride around town and through history
“Streetscape Curator” Matthew Dickey cycles around Boston finding architectural gems to create a digital scrapbook of pictures and a little history.

ON A BIKE — Everyone knows Acorn Street, the persistently popular Beacon Hill alley where photographers and social media influencers swarm the riverstones for picture-perfect online content. Or the brick Worcester Street home in the South End made famous — for better or worse — by an Instagram-savvy crowd.

But sometimes, to find Boston’s true hidden gems, you have to really work for it.

So on a recent Friday afternoon, Matthew Dickey pedaled his bike up a steep incline in Mission Hill to Alleghany Street, a spot where he had never been before. It was there he was hoping to find a stunning home hiding off the beaten path, as they often do around so many of the city’s corners.


Sure enough, a squat Italianate-style home quickly grabbed his attention.

“Look at this house!,” said Dickey, 37. “It’s perfect!”

He ogled its “curious” shape and mansard roof, as well as its well-maintained wooden siding, and zeroed in on its elaborately carved wooden door.

He took out his iPhone and snapped a photo.

Perhaps someday you’ll discover it on Dickey’s popular Instagram page, where he goes by “streetscapecurator,” and acts as an ambassador for the lesser-known abodes tucked into Boston’s historic neighborhoods.

It’s not just a hobby. By day, Dickey is communications director for the Boston Preservation Alliance, a nonprofit that strives to keep aging, noteworthy properties intact. Both at work and on Instagram, where he has 37,000 followers, he wants to change the way Boston thinks about its architectural treasures — before it’s too late to save them.

“Aesthetics and beauty are a way to get people [to care]. It could be in decorative tiles, or the details of a window, or an entire building that speaks to you,” Dickey said. “If people don’t really care about a thing being there, it’s not going to survive. It’s not going to continue.”


To locate these types of details, Dickey sets out on his bicycle almost daily, carefully scanning and scouting the city’s landscape for structures worthy of admiration.

Making his way to Sussex Street in Roxbury, he pointed to an addition on the side of an historic apartment building that once belonged to a descendent of founding father Robert Treat Paine, and whose current owner had clearly taken steps to match the original brickwork and window design.

“To me, that is really good architecture. It makes it something that is not noticeable, it fits right into its context, and enhances its space,” he said. “It’s built into its environment. It’s hunkered into its history.”

Later, as he pedaled through Rutland Square in the South End, he turned his attention to a collection of unusual marble busts in a row house’s façade. Statues of famous figures — often philosophers — aren’t uncommon in Renaissance revival-style homes in Boston, Dickey said. But these weren’t faces he recognized.

“Who are you!?” he shouted, as he took a picture. A mystery to unravel later.

Matthew Dickey poses for a portrait in Bay Village Neighborhood Park on Friday. Dickey has made a name for himself online as the "streetscapecurator," a popular Instagram account where he photographs, and sometimes paints, the old Boston homes he finds on daily bike rides.Erin Clark/Globe Staff

After he captures an image and returns home, the research begins. Dickey sometimes turns to the Boston Public Library’s Atlascope tool, used for exploring historic urban maps, to see how streets once looked. Other times, he looks for insights in the Massachusetts Cultural Resource Information System.

Some Boston properties rich with history are at risk of disappearing. He recently tracked down the city’s oldest triple-decker, located near the South Bay shopping center, and biked over to see it in person. But he was too late: It was quietly demolished last year.


For Dickey, that was a shame. He and members of the BPA advocate for “recycling” old buildings, rather than replacing them.

“Basically, we run on the adage that there should be no buildings torn down, because everything should be reused,” he said.

Dickey stressed that he and his colleagues aren’t opposed to new buildings — or building styles — sprouting in Boston. But they’d like its architectural history and character to remain, even as the city grows.

His meticulous preservation-by-bicycle approach to spreading that message can be rewarding. But it’s also a time-consuming process. To capture these under-appreciated structures in their best light, without obstructions like parked cars, he often visits homes several times in order to get the perfect shot.

“There are also times when I have my favorite spots, and I check in on them like an old grandparent,” he said. “Like, ‘Ooh, you’ve got new gutters now. You’re looking good!’”

When he’s not training a lens on buildings, he often turns his photos into paintings, posting his favorites on social media. While he takes commissions, Dickey also uses his artwork to raise money for historic preservation efforts.

His devotion to charming old homes has attracted attention beyond Boston’s borders. This year, he was recruited by the influential Instagram account “Accidentally Wes Anderson,” which shares images that look like scenes from the “Moonrise Kingdom” director’s movies, to explore the East Coast while taking pictures of antique post offices.


But as Dickey will tell you, you don’t have to travel far to find beautiful streetscapes. Just keep your eyes peeled.

Pedaling through the Frederick Douglass Square Historic District, he pulled his bike to a stop in front of a pair of doorways on Greenwich Street. The mid-afternoon sun was cutting through the trees, adding texture to the 122-year-old brick apartment building and a pile of colorful leaves bunched up on the sidewalk.

He pulled out his phone.

“That’s good,” he said. “That one can make the ‘gram.”

Matthew Dickey photographs the facade of a home that he found interesting while exploring Boston neighborhoods.Erin Clark/Globe Staff

Spencer Buell can be reached at Follow him @SpencerBuell.