Renovations on the Washington Avenue location of Dig Inn had hit a wall.

Earlier this 12 months, the New York-based mostly informal eating chain was shifting into the Outdated Nook Bookstore, the oldest industrial constructing in Boston, and struggling to vent an exhaust line for higher cooking capabilities.

The constructing, constructed in 1718 and tucked snugly between neighboring companies, got here with low ceilings that weren’t conducive to in depth duct work. Finally, staff stumble on an answer: Quite than working duct work by means of a aspect wall or roof, as is typical, they ran the exhaust line out the again of the constructing, into privately owned air area (with permission), and up.

“If you go right into a constructing like this, it’s costly,” stated Dig Inn founder Adam Eskin. “Loads of what you’re coping with, you don’t know you’re coping with it till you get in.”

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Such unconventional renovations should not unusual when 21st-century companies try to maneuver into antique Boston buildings. Squat brick buildings don’t supply a lot flexibility for contemporary, adaptive reuse. And whereas vacationers could also be bewildered — or aghast — to discover a chain restaurant inside a cease alongside the Freedom Path, some preservationists argue tenant with deep pockets and creative imaginative and prescient can save such buildings with out sacrificing historical past.

The Dig Inn renovations price the corporate about $ million over 5 months. However to Eskin, a South Shore native, the funding was price it.

“I’m from Boston initially, so I actually have a number of love for town and type of what it seems to be like and the way it feels,” Eskin stated. “The constructing itself and the way it units up was actually vital for us.”

Contractors included the present doorways and home windows into the brand new design, Eskin stated, and made choices about signage, coloration palette, and mechanical installations with the constructing’s historical past in thoughts.

Dig Inn rents the area on the Outdated Nook Bookstore from Historic Boston Inc., which buys and refurbishes a few of Boston’s oldest buildings.

“It’s fairly actually a gaggle of individuals standing in entrance of the wrecking ball,” stated government director Kathy Kottaridis.

The nonprofit is behind one of many extra recognizable reuse tasks in downtown Boston: the Chipotle location that now shares the Outdated Nook Bookstore on Washington Avenue.

Earlier than Chipotle moved in, Historic Boston Inc. refurbished the Outdated Nook Bookstore to some extent of fundamental inhabitability. The informal Mexican restaurant chain was answerable for the majority of the renovations, together with greater than $130,000 of duct work, in keeping with work permits filed with town.

Work of that scale might drown an impartial retailer, but it surely’s barely a drop in the bucket for an organization like Chipotle, which posted almost $four billion in income final 12 months, in keeping with firm filings.

Renting the Outdated Nook Bookstore area to Chipotle, Kottaridis stated, was not supposed to obscure the constructing’s literary previous, however as a substitute to make sure the nook’s financial viability for the longer term.

“Within the present market, the present world, a bookstore and even a publishing home would have a really onerous time sustaining itself in a downtown location,” Kottaridis stated.

Nonetheless, the Outdated Nook Bookstore-turned-Chipotle is among the first stops on the Freedom Path and infrequently puzzles vacationers and passersby.

“Why is it a Chipotle?” Laura Bailey requested throughout a latest trek on the path. “I’m ashamed for that one. It’s a key cease on the Freedom Path, and it will get an entire web page [in the guidebook], and so they didn’t make an effort to maintain that from occurring.”

Bailey was visiting from Charlotte, N.C., and had cut up up the total Freedom Path journey into two days along with her husband, John, and 14-year-outdated daughter, Emily.

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

Such adaptive reuse tasks will be discovered throughout town, as retail and actual property markets shift.

Historic Piano Row on Tremont and Boylston streets now features a movie show and burger restaurant, amongst different issues. The Customized Home constructing on State Avenue, which dates to the 1850s, is a Marriott Trip Membership Pulse resort and time-share. The pre-1900 Harvard Avenue Hearth Station in Allston homes a karaoke bar and Brazilian neighborhood middle.

“Issues change and markets change, and the concept that we will adapt that constructing and but hold it and interpret it and inform its story, is a good alternative,” Kottaridis stated of Historic Boston’s work on the Outdated Nook Bookstore.

Nonetheless, she says, a contemporary use in line with the constructing’s historical past is most popular.

Jamaica Plain’s Haffenreffer Brewery is a main instance: Almost 150 years after the brewery first opened, the constructing has been refurbished and rented out to new tenants — anchored by Boston Beer Firm, brewer of Samuel Adams Boston Lager.

The historic Dobson and Paramount theaters in downtown Boston, too, mirror their famed beginnings. Each theaters fell out of use round 1980, after many years of performances and film screenings. Years later, the theaters have been bought by native universities and refurbished. Theatergoers can nonetheless catch a present the place a few of Boston’s earliest have been first staged.

However reuse with a nod to the unique goal can usually be counterproductive to salvaging the constructing, stated Lara Kritzer, principal planner at JM Goldson Neighborhood Preservation and Planning, a Boston-based mostly historic preservation consulting group.

“I believe we’d all ideally wish to see one thing distinctive and weird and of that native place,” Kritzer stated. “However alternatively, if a retailer can’t stand and it takes out the constructing in the method, that’s not serving anybody.”

Because of this, preservationists are sometimes extra pragmatic than they’re given credit score for, she stated.

“Individuals anticipate us to say that it needs to be a shoe retailer as a result of it’s all the time been a shoe retailer, it needs to be a manufacturing facility as a result of it’s all the time been a manufacturing facility,” she stated. “The ones which have failed are those which have been too tightly knitted in — that is what it’s all the time been, and that is what it needs to be.”

Preservation in the long term usually means flexibility in design and establishing financial viability, she stated.

However bringing in too many nationwide manufacturers dangers altering the character of the neighborhood, in keeping with David Kirk, principal agent at Kirk & Firm Actual Property Counselors.

Unbiased retailers are sometimes extra delicate to the nuances of a neighborhood, Kirk stated. Nationwide chains transfer into city with established, high-down building fashions and enterprise practices that don’t bend to native wants as simply, he stated.

“I believe initially it was very powerful for nationwide chains that have been used to creating on pods in the suburbs with their cookie-cutter demographic screens to contemplate downtown, interval, a lot much less a historic neighborhood,” Kirk stated. “And a few of them have stumbled and crumbled and walked away.”

Those who keep, he stated, drive foot site visitors and contribute to a balanced tenant combine, which in flip contributes to the financial stability of a historic district.

“I believe there’s an idealized view of a number of the buildings in town and the place they stand,” stated Greg Galer, government director of the Boston Preservation Alliance. “We don’t need Boston to be like each different metropolis.”

Sara Salinas will be reached at sara.salinas@globe.com. Comply with her on Twitter at @saracsalinas.