Year: 2025

Filling in the Canvas

Raipher Pellegrino stands near the huge curved window on the second floor of the property at 280-302 Worthington St., known as the Underwood Building.

Raipher Pellegrino paused at the huge, curved second-floor window facing the corner of Worthington and Dwight streets.

“How’s that for a view?” he asked rhetorically, noting that it’s been quite some time since anyone — other than those he’s had out for tours — has looked out that window, some recent history he intends to change.

Indeed, he envisions a Pilates studio, a gym, or something similar on the second-floor space at 280-302 Worthington St., a property known as the Underwood Building, which has been vacant or mostly vacant for more than decade. And that space is just part of a much larger canvas that Pellegrino, the noted personal injury lawyer and real estate developer, working in partnership with his brother, Joseph, and the city of Springfield, is intent on filling in.

While doing so, he’s writing the intriguing next chapter in the history of what has been called (and is still called, even though it hasn’t lived up to the title) Springfield’s ‘entertainment district.’

This is the Worthington Street corridor, specifically the blocks just west of Dwight Street. It has been growing increasingly quiet over the past decade or so as restaurants, clubs, other businesses, and even a nonprofit (Suit Up Springfield) have shuttered or moved. The closing of Dewey’s Jazz Lounge last month was just the latest blow for the area.

It was with the intent of reinvigorating that corridor that Pellegrino and his brother acquired the three buildings east of Duryea Way at auction in 2021. With support from the city in the form of a $2.5 million grant and infrastructure improvements, Pellegrino is filling in his canvas.

Some of the spaces have been filled, like Petra Hookah Lounge, which features Mediterranean food and reopened last fall in extensively renovated space. Others are nearing completion, such as the new restaurant called Mamou, to be owned and operated by the chef at the former Chef Wayne’s Big Mamou, set to open this summer. And still others, including three more restaurants, a music venue to host between 250 and 400 people, and other businesses, like that projected Pilates studio, are still weeks or months away. Meanwhile, several residential units have been renovated, and more will be added to the mix.

“I think it’s vitally important to bring this area back — it raises the quality of living for those living downtown, and it provides places for people to go and eat. That was my desire with this, and it’s a much more difficult project than I think anyone envisioned, but I think we’re starting to see it evolve, and we’re seeing a lot of momentum.”

“The pieces are coming into place,” said Pellegrino, who envisions five restaurants in all, most with doors opening out onto Worthington Street and outdoor dining, in addition to a club and other businesses that will support one another and bring people — and energy — back to the Worthington Street corridor.

“I think it’s vitally important to bring this area back — it raises the quality of living for those living downtown, and it provides places for people to go and eat,” he said. “That was my desire with this, and it’s a much more difficult project than I think anyone envisioned, but I think we’re starting to see it evolve, and we’re seeing a lot of momentum.”

Tim Sheehan, Springfield’s chief Economic Development officer, agreed, noting that the city has invested more than $3.2 million in the entertainment corridor for everything from outdoor dining facilities to small-business assistance to interior buildout for commercial tenants.

This ground-floor space in the Underwood Building is being renovated for use as a music venue, what Raipher Pellegrino describes as an “Iron Horse-like” facility.

“The city’s investment continues in the corridor, and with what’s coming forward, people will see a lot of different options relative to dining in the dining district,” he said, adding that the goal is to bring both new businesses and a degree of long-term stability to a region that has not seen much of the latter.

Indeed, Brian Connors, deputy Development officer for the city, used understatement when he said the entertainment district has had “ebbs and flows.”

By that, he meant some good times, but also controversy with several late-night/early-morning incidents, and, from a business perspective, a high degree of turnover when it comes to restaurants and other businesses, problems compounded by the natural-gas explosion a block away in 2012.

For this issue, BusinessWest takes an in-depth look behind the plywood and brown paper over the doors and windows along that stretch of Worthington and into the future of the city’s entertainment district.

Work in Progress

It was raining intermittently as BusinessWest took its visit to the properties being redeveloped along that block on Worthington Street. The showers quickened the pace of the walks between the buildings, but they could hardly dampen the enthusiasm Pellegrino brought to his work as erstwhile tour guide, something he’s been doing often.

“This is a labor of love,” he said of the project, which is now approaching roughly $6 million in cost and represents perhaps the most extensive undertaking in a growing portfolio of real estate projects in Pellegrino’s portfolio.

That list includes the property at 265 State St. in Springfield — the large home later populated by commercial tenants but vacant in the ’90s and then restored by Pellegrino as a home to his offices — and its adjoining carriage house.

But it also includes a diverse mix of other properties, from charter schools in Springfield and Lowell, where Pellegrino went to college as an undergrad, to Springfield Country Club, which he acquired in partnership with the Hannoush brothers; from the property at 401 Liberty St. in Springfield, a former wire-manufacturing complex, now home to Behavioral Health Network, to the former Lunt Silversmith property in Greenfield, now home to a substance abuse center and mental health offices.

“The tenancy that we have needs to be established tenancy. In terms of going into the restaurant business as a startup business, it’s very, very difficult, and if the business model isn’t spot on, you have a tendency to have what we’ve had — businesses come in, businesses go out, businesses come in.”

Often, the projects involve properties that are historic in nature that require considerable renovations and modernization. Such is the case with the Worthington Street properties, which comprise a new challenge and a tremendous opportunity to reshape and reinvigorate the entertainment district, said Pellegrino, who started his tour at Petra Hookah Lounge, which opened its doors last fall, with the intent of showing what will be happening at the other properties along the street.

The block-long string of properties includes three buildings: 250-270 Worthington St., 272-280 Worthington, and 280-302 Worthington. The first two were built in the 1880s, and the third dates to the early 1930s.

Moving west to east, the properties were in progressively worse condition, he told BusinessWest, adding that 250-270 Worthington, most recently home to Jackalope Restaurant and now Petra (next door), was in decent shape, although both the residential units and restaurant spaces needed upgrades, including new HVAC systems. The property at 272-280, formerly home to several different restaurants, was in worse shape, he said, while 280-302 was “horrendous … uninhabitable.”

Efforts to make it habitable are among the many going on concurrently along that block, a project that came, as Pellegrino noted, with plenty of challenges — everything from renovating historic but badly deteriorated structures to securing established tenants — which became clear as he walked and talked about each of the buildings and the progress being made.

“With historic buildings like these, including one that hadn’t been occupied in 15 years, there are a lot of challenges,” he said, listing everything from floors one could see through to roofs that needed replacing to staircases that no longer meet code and need to be replaced. “This is a project that you can only figure out as you do it; we’ve systematically started at one end, 250-270 Worthington Street, and are working our way to the other.”

Starting with 250-270, he said Petra is now an established tenant, and there will be a new restaurant moving into the former Jackalope space by August or September. He declined to say what the entity will be but noted that it is an already established Springfield restaurant.

Raipher Pellegrino projects that five new restaurants, a music venue, other businesses, and new residential units will take shape along Worthington Street, reinvigorating the city’s entertainment district.

At 272-280, another new restaurant, Mamou, is expected to open later this month, and another new restaurant, a “bar-like” establishment with light fare, will be opening in the fall, he went on, adding that 280-302 Worthington will have a music venue, a breakfast/lunch restaurant, and other commercial spaces, six units in all, with tenants yet to be identified.

The music venue he’s envisioning will not compete with but rather complement existing venues such as the MassMutual Center, Symphony Hall, and the former CityStage, now being renovated into an arts center for youth, and be an “Iron Horse-like” venue, he said, a reference to the Northampton landmark that reopened last spring.

“The concept is to offer people live entertainment, but also support the restaurants,” Pellegrino said. “If you have an act and sell 250 to 400 tickets, people will want to eat before that.”

Building Momentum

As he stopped at that massive, curved window in the second-floor space above what will be the music venue, Pellegrino pointed to all the parking in the surrounding area, one of the many keys to the success of this project and the entertainment district overall.

Others include everything from improving the perception of public safety to creating stability with the business mix, as well as that supportive element that he mentioned.

Indeed, as the canvas gets filled in, the entertainment district will have a core of new restaurants and businesses, as well as some established eateries — Theodores’ and Del Rey Taqueria on Worthington Street, Osteria on Bridge Street, the nearby Student Prince, and other restaurants and taverns that will support one another, said Pellegrino, adding that the critical mass in his block of buildings should become a draw.

“All of the tenants understand the synergy — there’s discussion about that, and they work well with one another,” he noted. “The idea is that maybe someone can have dinner in one place tonight and have a drink in your place the next night; it feeds off one another. The more people we pull down into the region, the better the restaurants will do. The idea is to create the entertainment district, and the more the merrier.”

Sheehan agreed, noting there are several other keys to the success of this iteration, if you will, of the entertainment district.

These include everything from bringing experienced restaurateurs with proven concepts into the area to infrastructure upgrades.

“The tenancy that we have needs to be established tenancy,” he noted. “In terms of going into the restaurant business as a startup business, it’s very, very difficult, and if the business model isn’t spot on, you have a tendency to have what we’ve had — businesses come in, businesses go out, businesses come in.

“Our objective is to get more stabilized entrepreneurs into the spaces, and I do believe the tenancy that [Pellegrino] is putting forward reflects that stability,” he went on, adding that infrastructure improvements continue in the area, including additional upgrades, including more uplighting and plantings, to Stearns Square, capitalizing on work previously undertaken at that landmark.

Overall, the city has made a large commitment — in funding but also other forms of support — to the stability and growth of the entertainment district, said Connors, noting that public sector support, in the form of loans and grants for initiatives like outdoor dining, interior renovations, and relocation costs, are critical at a time when banks are often reluctant to lend for restaurant and brewery initiatives.

Pellegrino agreed, adding that the investments being made in the three properties along that block of Worthington Street and the individual spaces for restaurants and other businesses are another factor in the success quotient.

“These are major facelifts … these are beautiful, state-of-the-art restaurants. They’re coming into beautifully renovated spaces,” he told BusinessWest. “There’s no guarantee that any restaurant is going to succeed, but this gives them the best opportunity to succeed.

“Everyone has to do their part,” he went on. “The restaurateur has to put out good food and atmosphere; we collectively, with the city, have to provide a safe atmosphere and parking, so it’s inviting, and people feel comfortable coming downtown.”

Whether this picture will come together as Pellegrino and city officials anticipate remains to be seen. But there is great anticipation about what’s behind all that plywood and brown paper.

It’s the next big chapter in the life and times of Springfield’s entertainment district.