“I once heard Quincy Jones tell an interviewer when he had an idea, he got it down as fast he could,” architect Jerome Gray says, opening a palm-sized watercolor set across the street from The 501, a midcentury modern apartment building on the edge of Seton Hill. “If it was 3 a.m. and he needed the best bass player in LA, he’d bring him to the studio tired, drunk, hungover, whatever. Better if they were tired because they wouldn’t overthink anything. You’re just capturing the essence.”

With that, Gray counts The 501’s front-facing windows and dashes off the frame of the building in a few pencil strokes. He immediately begins adding color—the pale blue sky absorbed in the building’s white facade, the midday sun reflected in its glass, its rust-orange accents. He chats through the entire exercise, which lasts just minutes. Then he walks to the corner, takes in the new perspective, and does it again, this time without an outline, only watercolor.

In a previous iteration, The 501 was owned by The Hardest Working Man in Show Business and named the James Brown Motor Inn. Opened in 1964, it mostly served a white business crowd before Brown purchased it for $5,000,000 in 1970. An FBI raid and developing “reputation for rowdiness” at the inn’s nightclub soon forced Brown to sell.

As Gray notes on his popular Instagram feed, where he posts brief histories alongside his watercolors, The 501 was designed by Baltimorean David Harrison, who also did Dolfield Plaza and Brooklyn’s Patapsco Theatre, which today has been repurposed into a church.

Over ensuing lunch breaks, Gray returns to Seton Hill, capturing the former home of a candy company and a furniture store owned by a man who also operated an illegal saloon during Prohibition. Many of his subjects are familiar—Camden Yards, the city’s gothic cathedrals, the American Visionary Art Museum, and the Art Deco Senator Theatre (pictured above), designed by John Jacob Zink, who studied at the Maryland Institute and did the iconic Patterson Theater as well. Everything is fair game and the watercolors that get the most engagement are often the fading, occasionally vacant wonders most of us pass by without noticing, including the 1870-built Home of the Friendless building on Druid Hill Avenue.

Since 2016, Gray has posted 3,300 sketches. “I’d gone into business for myself and it wasn’t ‘going’ yet, and my wife told me I needed to get out of the house,” he recalls. “She said, ‘Didn’t you used to draw?’”

Most of his works depict Baltimore’s built environment, although there are sketches of D.C., Philadelphia, Pittsburgh, Cleveland—“a city with great architecture”—and Detroit, his hometown. Emulating an older brother who drew, Gray got good with a pencil at a young age and excelled in the architecture program at Detroit’s legendary Cass Technical High School, whose notable alumni include John DeLorean and Diana Ross.

“I was in a good-size class of Black kids, if you can imagine this in the 1970s and 1980s, who were put through the wringer,” he says. “My best friends were in the program, and we were all going be architects. Lo and behold, three of us became architects. The fourth one became an engineer.”

Completely unplanned, his watercolors garnered attention from local architects, historians, and preservationists and became a career boon, leading to exhibitions and commissions. Gray gave the keynote address for the 2019 Doors Open weekend sponsored by the American Institute of Architects-Baltimore and joined the Baltimore City Historical Society board. He now regularly presents on urban architecture and history.

Are there buildings he wants to get to? “Always,” he says, naming WEBB’s old radio studio, which James Brown also owned, in West Baltimore’s Fairmount neighborhood. He also wants to check out the views from Johnston Square on the east side.

“The one I want to do, but can’t, is the Mechanic Theatre, which was demolished. There are good reasons to knock down buildings, but there was no reason to demolish the Mechanic. It was designed by an important American modernist architect, John Johansen, whose work in other places is celebrated. The Mechanic was an amazing exercise in broken-form concrete. It was this complex, broad-shouldered, tough building that was honest to what it was—a concrete building. It was corrupted over its time, but it should’ve been loved. Instead, we still have a big hole in the middle of the city eight years later.”

(Gray warns not to get him started about McKeldin Fountain, another brutalist landmark demolished with support from the Downtown Partnership.)

“One of the significant things about modernism, which is about the only architecture movement people don’t seem to like, is brutalism,” Gray explains. “You may not like it, but it played with form and depth and shadow and light better than just about anything. I think what people like [in my sketches] is the color and the contrasts, but that’s the thing, the architect’s vision, I’m trying to communicate.”

Jason Freeman is like an avid birder—but instead of feathered friends, it’s historic homes he’s observing, and his equipment of choice isn’t binoculars but the camera of his trusty iPhone.

Freeman, the founder, researcher, and often the main photographer of the @historichomesofbaltimore Instagram account, has slowly built his audience from a handful of local friends and family to over 18,000 followers that come from such far-flung places as Georgia, Missouri, California, and Louisiana. They scroll a few times a week as Freeman posts homes he encounters on his daily walks and runs around Baltimore—historic photos of residences, places for sale, favorite spots in the city, and “historic hidden gem neighborhoods.”

Despite his love for Charm City dwellings, Freeman didn’t grow up here, nor does he have a background in architecture. Instead, the 31-year-old upstate New Yorker and data analyst for Catholic Relief Services moved to Baltimore five years ago and relocated around the city—Mt. Vernon, Federal Hill, and Roland Park—as his family grew. He was charmed by what he saw. “My phone has always had lots of photos of random homes that I’ve taken while I was walking or running,” he says. But it was strictly a hobby at first, and the photos just sat on his phone.

The Instagram account was born the same month as his son, in June 2019. Freeman and his wife had just moved into an apartment near the Roland Water Tower in Roland Park, and he found himself spending hours strolling his newborn son through the streets, as a bleary-eyed parent desperate for baby slumber often does. Every block was better than the one before, with home after home resplendent with architectural details and frozen in time from their dates of construction. “I just started wondering about the history—when they were built and who lives there,” says Freeman.

Three years and 600 posts later, Freeman is consciously curating his account, weighing the exquisite beauty of a home with the history of how it came to be. “I try to balance beautiful homes with sharing the history surrounding them,” he says.

Along with taking photos, he started digging deeper into the homes’ past and sharing what he gathered. Sometimes what he uncovers isn’t so sunny.

One example, when the Roland Park Company was developing Plat 2 in the late 1890s—Roland Park is divided into six plats—they discovered they didn’t own a half-acre plot of land they needed to build on. It turns out it was owned by Solomon Moonier, a Black man who bought the land in 1802 and built a home and family burial ground. By the time Roland Park was being developed, Moonier had died and 12 of his heirs were identified. The company “worked within a legal system that discounted Blacks’ claims to property and negotiated in bad faith,” ultimately paying only $800 to be split between his descendants, according to How the Suburbs Were Segregated by Paige Glotzer.

As part of the purchase, the Roland Park Company gave the family six months to remove the bodies in the family graveyard, or the company would do it itself. The historic photograph Freeman posted on July 1, 2021, shows houses located around the corner from what was the Moonier property—now Oakdale Road. Without the accompanying text it’s just a pretty picture—with it, it’s history.

His IG Stories include other book recommendations that also delve into the sticky history of the city. “When I first started, I didn’t fully understand how intertwined Baltimore’s history with race, segregation, and racism was tied to the homes I was looking at,” says Freeman.

That learning curve also meant extending the areas he was exploring. Instead of just sticking with the zip codes he lived in, worked near, or visited to see friends, he started seeking out new communities.

“I try to be more intentional about featuring a mix of neighborhoods,” says Freeman. “I’m going out of my way to go to areas that I might not otherwise go to or where I don’t necessarily know people that live there to try and share stories from all over the city.”

That meant checking out Tuscany-Canterbury, Arcadia-Beverly Hills, Dickeyville, Windsor Hills, Original Northwood, Ednor Gardens, and Union Square. “I probably wouldn’t have learned about some of these neighborhoods if I wasn’t doing this page,” he admits. Sometimes Freeman just snaps a picture and posts it because it’s attractive—great door color, curb appeal, or unique characteristics. Other times, he’ll make a note of the address and delve into the genealogy of the house or its inhabitants, from AIDS activist John Stuban’s tiny rowhouse in Mt. Vernon to a stunning mansion on what is now Loyola’s campus, initially built by an heir to the B&O Railroad fortune as a wedding gift to her son and his new bride.

His followers eat up these stories. Some are people who grew up in Baltimore or went to school here, and while they’re no longer residents, are nostalgic for the city’s unique rowhomes, Victorians, and cottages. “I get messages about how nice it is to see some of the streets that they remember growing up on,” he says. However, a big chunk of Freeman’s followers are current dwellers. “Every so often I’ll get a message like, ‘Yay, you finally shared my house.’”

He has become part cheerleader for the city and part detective, often spending time on the Johns Hopkins Flickr account or digging through neighborhood archives. Sometimes, Freeman will just seek out things that he’s always wondered about—like the Telescope House in Original Northwood. The Tudor Revival home was built in 1931 with the copper rooftop observatory added in 1937, both designed by John Ahlers.

“The observatory was built for Joseph L. Woods, a toy manufacturer and amateur astronomer. He was particularly interested in photometry and variable stars and had ties to Harvard University and the University of Pennsylvania,” Freeman says. Luckily, when it was built, the surrounding area provided enough darkness for good nighttime views.

Freeman is also the first to admit he doesn’t know everything. “Some of the fun of the page is I’m learning from other people,” he says. If he doesn’t know something (say the style of a particular house), he’ll throw it to his followers. They almost always know. “Often they do have a background in architecture,” he admits. “I always feel like I’m learning a lot from other people. And I try and approach the page like that too.”

Lately, Freeman has been leaning into IG reels, with music and text accompanying some of his posts. He’s still doing “for sale Friday,” one of the few days people get to see the actual inside of the homes on his account. Part of it is his own curiosity—he and his wife are house-hunting—and part of it is just scratching that insatiable itch of knowing what’s behind the front door.

And the best thing about Baltimore? There will always be more houses to cover, providing Freeman has the time and interest. There’s so much history here, he says—each historic neighborhood like an archaeologist’s dream—something that doesn’t exist anymore with McMansions and cookie-cutter developments. That’s even more reason why historic home preservation—and an Instagram account dedicated to their survival—is so important.

“A lot of people love old houses, but I think sharing it to a wider audience is always fun,” says Freeman. “These homes have a lot of great stories; they are beautiful, but they’re pretty rare. So that’s kind of special.”