COMMUNITY MATTERS: Activating people committed to place
The Westside Legends have achieved great success in building community in partnership with residents in the neighborhood.
Westside Legends provides a micro-loan to local business Berkshire International Market. Pictured here on March 17, 2025, are (l.) Goundo Piere Behanzin, owner of Berkshire International Market, with Marvin Purry, treasurer of Westside Legends. Photo courtesy of Westside Legends
“It’s our turn.”
This sentiment has long defined the leaders and participants of the Westside Legends (WSL), an organization dedicated to preserving the community spirit and revitalizing Pittsfield’s Westside neighborhood. Those involved in the WSL see how the neighborhood helped shape their lives, and they want those qualities to remain strong.
Generations of families have called this predominantly Black neighborhood home, with children growing up together, attending the same schools, and playing on the same sports teams. These deep-rooted relationships create a strong sense of community and a profound connection to the neighborhood. Yet, the Westside also bears the scars of systemic racism from decades of real estate redlining. It also felt the brunt of urban renewal when the city constructed a bypass that severed the Westside from downtown.
Despite these challenges, the Westside Legends have achieved great success in building community in partnership with residents in the neighborhood—public art installations, cultural events, hosting a regional soapbox derby competition, and developing affordable housing. At the heart of all these efforts lies a strong dedication to place.
Connections, old and new
The annual soapbox derby, scheduled again for August (date tbd), is one of many Westside Leaders events that bring the community together. Photo courtesy of Westside Legends
Sports and the rivalries they inspire run deep in most communities, and the Westside neighborhood is no exception. The origins of Westside Legends (WSL) can be traced back to a shared desire among former teammates to reconnect. What started as a Facebook page started by longtime WSL leader Tony Jackson quickly grew, drawing in more people eager to talk about past sports teams and wonder where their old teammates had gone. The sharing of old photos sparked lively debates over which teams had been the strongest, rekindling old friendships and creating new connections among those united by the shared experience of growing up in the Westside and Pittsfield.
Paying it Forward
As conversations grew, WSL members recalled past events that had once united the neighborhood—concerts, picnics, and soapbox derbies. A deep pride in the Westside emerged from these social connections, fostering a collective determination to give back to the community.
Around this time, Pittsfield was developing the new Riverway Park in the neighborhood. The city aimed to involve residents in the park’s design, but skepticism lingered due to the city’s history with the neighborhood. Recognizing this, the city sought a partner, and the Westside Legends stepped up, determined to make the park a neighborhood asset that residents could truly call their own. They worked with city planners, led by architect Tessa Kelly, to engage residents and encouraged the community to see the park as a space for connection and creativity through the arts.
“Rainbow Ruby” in Riverway Park honors Ruby Bridges’ historic walk to school in 1960,. This was Westside Legends’ first public art project. Photo courtesy of Westside Legends.
This collaborative process and the resulting park plan mobilized the relationships WSL had been building, uniting the neighborhood around the arts as a way for community building. This vision extended to a public art project, Rainbow Ruby, which honors Ruby Bridges’ historic walk to school in 1960, a defining moment in the fight for civil rights and racial equity. This summer, WSL is completing its second public art project, paying tribute to the 54th Massachusetts Volunteer Infantry, the first Black regiment to fight in the Civil War that holds a key place in American history. The regiment was initially formed in Pittsfield, with fourteen families from the Westside community sending their sons to fight in the Civil War.
Inclusive Leadership and Incremental Progress
With financing from Greylock Federal Credit Union, arranged by Westside Legends, Lemon and Betty Wilder are able to buy a house for the first time and plan to leave it to their sons. Photo courtesy of Westside Legends
These early experiences established the Westside Legends as a significant organizing force within the neighborhood, with the ability to tackle pressing issues such as housing. Their attention was drawn to the fact that 34 houses in the neighborhood had been condemned by the city—34 home sites that would no longer be available to residents. For the WSL, this loss of housing meant fewer families could remain in the Westside, which became a clear call to action. How could the WSL help increase homeownership by actively redeveloping these sites into affordable housing that would enable residents to build equity and secure their futures within the neighborhood? They set their sights on tackling this challenge.
Over the past seven years, WSL has formed strategic partnerships to direct resources toward the goal of increasing homeownership among Westside residents. They worked with the City of Pittsfield to identify opportunities for redeveloping condemned home sites and teamed up with Greylock Federal Credit Union to prequalify residents for affordable financing. Additionally, they have rehabilitated existing homes to serve as rental properties, creating pathways toward eventual homeownership.
One of their most important projects is now on the immediate horizon: the development of 16 affordable townhouses in partnership with the City and MassHousing, pending final approval. This initiative is a major step forward in creating sustainable, equitable housing for the neighborhood—and the WSL is just getting started.
Westside Legends is awaiting approval to build 16 affordable townhouses in partnership with the city and MassHousing. Photo courtesy of Westside Legends.
One of the Westside Legends’ key strengths is its ability to build intergenerational connections and leadership. By bringing residents and partners together, the WSL can move forward with important projects identified through the WSL network. Their visible successes include new housing developments, the annual soapbox derby that attracts young competitors from across the region, and public art projects that help shape the neighborhood’s identity. What also stands out is the deep commitment to the Westside and its residents, a dedication that continues to grow through the collective efforts of the organization.