Westside Legends began informally as an effort to honor the personal family histories, community leaders and social connections that founder Tony Jackson and his friends experienced growing up on the west side of Pittsfield. Since 2018, Westside Legends (WSL), now a 501 (c) (3) nonprofit, has matured into a powerful, all-volunteer run neighborhood revitalization organization. WSL collaborates with a network of community partners and allies that share its vision of re-establishing the west side as a vibrant and healthy neighborhood that will in turn strengthen the city of Pittsfield as a whole. WSL’s comprehensive view for a strong west side includes increased homeownership, healthcare support, community gardens, colorful murals, and social gatherings like the “Neighborhood Block Party” and “The Brian Goines Sweet G Super Soap Box Derby.”

Jackson (President), Beverly Bolden (Vice President) and Marvin Purry (Treasurer) focus their efforts on finding creative ways to “give back” and invest in the future of the neighborhood that nurtured them as youths and allowed them to progress forward and build successful lives. (Hear their stories). Each initiative plays a role in catalyzing more positive change and in re-establishing features of an area that has shifted over the years from a beautiful neighborhood where several families owned their homes to one comprised mostly of rental units, with little-to-no new business investment or construction of homes. Jackson, now living in Atlanta, GA, recalls coming home to visit over the years and seeing the neighborhood slowly deteriorate, with vacant lots resulting from houses torn down by the city due to blight.

A 2022 study funded by the Berkshire County NAACP and Greylock Federal Credit Union illuminates a major contributing factor; it reveals a 1937 federal “New Deal” map designed for investors that “redlined” a significant portion of Pittsfield’s west side. The departure of the General Electric plant from Pittsfield in the early nineties (that at its height employed 12,000 people) left the town’s local economy on tenuous ground and exacerbated the legacy of disinvestment already taking hold on the west side.

New Townhouses Will Offer a Unique Opportunity to First-time Homebuyers on the West Side

Westside Legends has teamed up with Group Architecture and Urbanism (Group AU) to design a development of 12-15 new homes at 363 Columbus Avenue. They hope to break ground in Spring 2025. Berkshire Taconic Community Foundation has contributed $30,000 toward the launch.

WSL’s townhouse project is unique in its framework and is a first for the west side. It is the result of a collaboration that includes vital support from MassHousing’s “Commonwealth Builder” program, which will buy down the building cost of each unit up to $250,000, making it possible to lower the sale price of each home to a range of $168,000 to $264,000.

Furthering their local impact on the homeownership front, the “WSL/Greylock Homeownership Program,” is a key joint venture with Greylock Federal Credit Union designed to increase applications and pre-qualifications for mortgages for lower-income people in Pittsfield. It has been a successful tool thus far in reducing obstacles to achieving homeownership and narrowing the gap for historically under-represented people, with 37 families closing on homes in the past two years. Over 90% of individuals and families pre-qualified under this program are Black or People of Color.

Additionally, WSL’s House Buy Back program has acquired three homes to date, one of which is ARPA (American Rescue Plan Act)-funded. The restoration of one home is complete and will be followed by the other two within the next couple of months.

Looking Forward to Creating Pittsfield’s Next Chapter

Jackson believes Pittsfield’s story is “just beginning” and is excited to see the next phases of WSL’s projects gain momentum and bring more positive energy to the city. A design competition for a local monument to honor Pittsfield’s African-American connections to the Civil War and the 54th Massachusetts Infantry Regiment is planned to coincide with Juneteenth. Dates for the block party, the derby and workshops to design and build the go-carts will be announced on their website soon. Additionally, the launch of a Westside Marketplace at Riverway Park and “Barbershop Talks” for men’s health, in partnership with Berkshire Health Systems, are planned.