Teddy’s on the Hill Set to Take Over Old Red Hat Space

As the owner of Teddy’s on the Hill , which is set to open before the end of the month in the Bowdoin Street space that was home for more than a century to The Red Hat, Jake Nicholson is well aware that he has been entrusted with carrying on the legacy of a fabled Boston institution.

“What we’re looking to accomplish when we open, first and foremost, is keeping the nostalgia of one of the most iconic spots in the city,” he said.  “And second, what can we do to give it a breath of fresh air for the neighborhood and everyone else?”

The former Red Hat space at 9 Bowdoin St., which will soon be home to Teddy’s on the Hill.
A look inside Teddy’s on the Hill.

Long before the inception of Teddy’s on the Hill, Nicholson, a more than 20-year veteran of the restaurant industry who most recently co-managed the now-shuttered Finn McCool’s in the Financial District, was already well acquainted with The Red Hat, which operated at 9 Bowdoin St. from 1907 until last June, as it was a popular destination for restaurant workers.

“I’ve been coming here for years,” said Nicholson. “Just being in the industry, it was one of the spots we always used to go come to after a game or something, so I had an idea of the what the potential was, and what it had been. I saw an opportunity for ownership and thought what better spot to do it in than one of the most iconic bars in Boston?

“If you’re going to be a bear, you mind as well be a grizzly,” he added.

Working alongside Nicholson at Teddy’s on the Hill is Courtney Nunheimer, general manager, beverage director, and self-described “jack of all trades.”

“I’ve known Jake for about a decade, and we wanted to do something special at this spot,” said Nunheimer, whose father, David Nunheimer, also worked at The Red Hat when he was attending Suffolk Law School.

And like Nicholson, Nunheimer also realizes what she sees as their obligation to create somewhere fresh and new in the space while still paying proper respect to The Red Hat of yore.

“There’s a lot of hesitation with the new ownership, obviously,” she said. “We took it to heart to make sure we didn’t demo the whole place and get rid of what people loved about it. We just gave it a refresh.”

Teddy’s on the Hill, like its predecessor, will span two separate floors.

“We talked to people in the neighborhood and some old patrons on what they’re looking for, and we really tried to take that into account,” said Nunheimer. “With the space being so unique with two different spaces, and because Beacon Hill has such a unique mix of people – college kids, grad students, people who live right down the street, and people who work in the area – they’re all looking for something a little bit different.”

Downstairs, known as “Old Scollay’s Darker Side” during the bar’s previous incarnation,  has undergone a deep clean and had more seating added. Much of what was downstairs before has been preserved, said Nunheimer, including some of the vintage photos that previously dotted the walls, along with some other old photos found unframed and tucked away during the renovations.

“We just kind of fixed things us that had kind of fallen by the wayside,” she said. “It’s an old building, and there’s a lot to keep up with.”

The wood-encased bar on the first floor that was a fixture of The Red Hat since it opened will also be returning.

“It was one of the biggest things that holds such a special place in so many people’s hearts…and a piece of history for that neighborhood,” said Nunheimer.

Formerly known as “Old Scollay’s Lighter Side,” the upstairs will be adorned with “a couple of pieces of décor items that are original to the building that were found during construction.” As for what these items might be, Nunheimer coyly replied she didn’t want to give much away prior to the new establishment opening.

Upstairs will have a drink menu featuring a wide selection of craft cocktails, with some crossover in beer and wines from the downstairs beverage menu. Nunheimer, who has a background in craft cocktails, said she wants the cocktail menu, which will rotate seasonally, to be “approachable.”

“We’re not trying to anything too crazy,” she said. “We’re trying to find a middle ground while putting out a good product, a fresh product.”

Added Nicholson, “We want to keep all the old regulars, and expand and bring in new people, and it’s a great opportunity with bars on both floors. People can enjoy the old school, iconic lower level, and on the upper level, there’s a little change, if they’re not looking for anything too fancy.”

Since The Red Hat was a popular destination for sports fans, there will be many spaces located throughout the new establishment to watch games as well.

Nunheimer describes the fare as “elevated pub food, American style.” Besides a menu featuring salads; “handheld items,” including sandwiches and several different burger selections; and myriad appetizers and other sharable items, she said, “The big thing is going to be South Shore bar pizzas.”

Unlike a traditional pizza, South Shore-style pizza are personal, 10-inch pies made in a pan.

“The best part is that the sauce and cheese go right to the very edge of the pan, and it’s got a crispy and buttery crust,” said Nunheimer.

When patrons see Teddy’s on the Hill for themselves, Nicholson and Nunheimer are both confident they will agree that the new establishment pays fitting tribute to the old Red Hat while simultaneously giving it a more contemporary spin.

“People are going to be pleasantly surprised,” said Nicholson. “Change is always tough, especially when the place is almost 115 years old, but people will be able to hold onto their old memories and embrace what’s new.”

Visit Teddysboston.com for more information on Teddy’s on the Hill.

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