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In Boston, 21st-century businesses are taking over historic buildings

Boston’s historic Custom House now houses a Marriott Vacation Club Pulse hotel and time-share. Barry Chin/Globe Staff

Renovations at the Washington Street location of Dig Inn had hit a wall.

Earlier this year, the New York-based casual dining chain was moving into the Old Corner Bookstore, the oldest commercial building in Boston, and struggling to vent an exhaust line for greater cooking capabilities.

The building, constructed in 1718 and tucked snugly between neighboring businesses, came with low ceilings that weren’t conducive to extensive duct work. Eventually, workers hit upon a solution: Rather than running duct work through a side wall or roof, as is typical, they ran the exhaust line out the back of the building, into privately owned air space (with permission), and up.


“When you go into a building like this, it’s expensive,” said Dig Inn founder Adam Eskin. “A lot of what you’re dealing with, you don’t know you’re dealing with it until you get in.”

Such unconventional renovations are not uncommon when 21st-century businesses attempt to move into antique Boston buildings. Squat brick buildings don’t offer much flexibility for modern, adaptive reuse. And while tourists may be bewildered — or aghast — to find a chain restaurant inside a stop along the Freedom Trail, some preservationists argue that a tenant with deep pockets and inventive vision can save such buildings without sacrificing history.

The Dig Inn renovations cost the company about $1 million over five months. But to Eskin, a South Shore native, the investment was worth it.

“I’m from Boston originally, so I really have a lot of love for the city and sort of what it looks like and how it feels,” Eskin said. “The building itself and how it sets up was really important for us.”

Contractors incorporated the existing doors and windows into the new design, Eskin said, and made decisions about signage, color palette, and mechanical installations with the building’s history in mind.


Dig Inn rents the space at the Old Corner Bookstore from Historic Boston Inc., which buys and refurbishes some of Boston’s oldest buildings.

“It’s quite literally a group of people standing in front of the wrecking ball,” said executive director Kathy Kottaridis.

The nonprofit is behind one of the more recognizable reuse projects in downtown Boston: the Chipotle location that now shares the Old Corner Bookstore on Washington Street.

The Old Corner Bookstore no longer facilitates book sales. You can buy a burrito, though.Barry Chin/Globe Staff

Before Chipotle moved in, Historic Boston Inc. refurbished the Old Corner Bookstore to a point of basic inhabitability. The casual Mexican restaurant chain was responsible for the bulk of the renovations, including more than $130,000 of duct work, according to work permits filed with the city.

Work of that scale could drown an independent retailer, but it’s barely a drop in the bucket for a company like Chipotle, which posted nearly $4 billion in revenue last year, according to company filings.

Renting the Old Corner Bookstore space to Chipotle, Kottaridis said, was not intended to obscure the building’s literary past, but instead to ensure the corner’s economic viability for the future.

“In the current market, the current world, a bookstore and even a publishing house would have a very hard time sustaining itself in a downtown location,” Kottaridis said.

Still, the Old Corner Bookstore-turned-Chipotle is one of the first stops on the Freedom Trail and often puzzles tourists and passersby.

“Why is it a Chipotle?” Laura Bailey asked during a recent trek on the trail. “I’m ashamed for that one. It’s a key stop on the Freedom Trail, and it gets a whole page [in the guidebook], and they didn’t make an effort to keep that from happening.”


Bailey was visiting from Charlotte, N.C., and had split up the full Freedom Trail journey into two days with her husband, John, and 14-year-old daughter, Emily.

“It was very jarring after all the sites we’ve seen,” Laura Bailey said. “It’s a travesty.”

Such adaptive reuse projects can be found across the city, as retail and real estate markets shift.

Historic Piano Row on Tremont and Boylston streets now includes a movie theater and burger restaurant, among other things. The Custom House building on State Street, which dates to the 1850s, is a Marriott Vacation Club Pulse hotel and time-share. The pre-1900 Harvard Avenue Fire Station in Allston houses a karaoke bar and Brazilian community center.

“Things change and markets change, and the idea that we can adapt that building and yet keep it and interpret it and tell its story, is a great opportunity,” Kottaridis said of Historic Boston’s work on the Old Corner Bookstore.

Still, she says, a modern use consistent with the building’s history is preferred.

Jamaica Plain’s Haffenreffer Brewery is a prime example: Nearly 150 years after the brewery first opened, the building has been refurbished and rented out to new tenants — anchored by Boston Beer Company, brewer of Samuel Adams Boston Lager.

The historic Dobson and Paramount theaters in downtown Boston, too, mirror their famed beginnings. Both theaters fell out of use around 1980, after decades of performances and movie screenings. Years later, the theaters were purchased by local universities and refurbished. Theatergoers can still catch a show where some of Boston’s earliest were first staged.


But reuse with a nod to the original purpose can often be counterproductive to salvaging the building, said Lara Kritzer, principal planner at JM Goldson Community Preservation and Planning, a Boston-based historic preservation consulting group.

“I think we’d all ideally like to see something unique and unusual and of that local place,” Kritzer said. “But on the other hand, if a store can’t stand and it takes out the building in the process, that’s not serving anyone.”

As a result, preservationists are often more pragmatic than they’re given credit for, she said.

“People expect us to say that it has to be a shoe store because it’s always been a shoe store, it has to be a factory because it’s always been a factory,” she said. “The ones that have failed are the ones that have been too tightly knitted in — this is what it’s always been, and this is what it has to be.”

Preservation in the long run often means flexibility in design and establishing economic viability, she said.

But bringing in too many national brands risks altering the character of the neighborhood, according to David Kirk, principal agent at Kirk & Company Real Estate Counselors.

Independent retailers are often more sensitive to the nuances of a neighborhood, Kirk said. National chains move into town with established, top-down construction models and business practices that don’t bend to local needs as easily, he said.


“I think initially it was very tough for national chains that were used to developing on pods in the suburbs with their cookie-cutter demographic screens to consider downtown, period, much less a historic neighborhood,” Kirk said. “And some of them have stumbled and crumbled and walked away.”

Those that stay, he said, drive foot traffic and contribute to a balanced tenant mix, which in turn contributes to the economic stability of a historic district.

“I think there’s an idealized view of some of the buildings in the city and where they stand,” said Greg Galer, executive director of the Boston Preservation Alliance. “We don’t want Boston to be like every other city.”

Sara Salinas can be reached at sara.salinas@globe.com. Follow her on Twitter @saracsalinas.