AN INCLUSIVE DOWNTOWN
LGBTQ + BUSINESSES IN PITTSFIELD ARE BUILDING, SUPPORTING ONE ANOTHER, AND THRIVING
B y T a y l o r S t a u b a c h
I n Pittsfield, belonging isn’ t something that’ s bought. It’ s built, door by door, conversation by conversation. Walk into WANDER Berkshires, and you’ re not just stepping into a cafe to grab a coffee. You’ ve wandered into a living, breathing incubator space for community hospitality. Founder Jay Santangelo describes it as a“ community third space,” a place where daytime energy, co-working, meetings, and casual gatherings naturally flow into evening programming: author talks, performances, craft and drag events.
WANDER’ s evolution is closely linked to the businesses around it. Berkshire Pride’ s office occupies the same building, Brazzucas Market sits around the corner, and Indie Readery & Records is a short walk away.
Santangelo recalls a Saturday morning that felt like a microcosm of something bigger. A caregiver group for trans and non-binary youth meeting took place at WANDER in the morning, alongside a meeting of the Hoffmann Bird Club. A Rainbow Seniors crafting circle gathered later, and a Scrabble club filled the space in-between. The groups thrived on their own quiet, intentional energy, filling WANDER with a shared atmosphere of collective enthusiasm.
Opened in January 2025, WANDER was part of the Transformative Development Initiative’ s( TDI’ s) Creative Catalyst Cohort, which received funds for the Downtown Pittsfield Creative Alliance. None of the groups that gravitated to
WANDER were“ recruited”; they just seem to find the place on their own.“ It’ s not a queer space,” Santangelo says.“ Yes, it’ s a queer and trans-owned space, and we do have a ton of queer-focused programming, but it’ s evolved into a community space, a third space for all that the community themselves are building and growing.”
Berkshire Pride Executive Director Cass Santos-China put it plainly during a visit.“ This is diversity at its core,” she told Santangelo.
The space also hosts a trans clothing exchange and community closet. A darkroom is expected to be operational by the time of this printing.“ Depot After Dark” drew large crowds last year, and there are plans to bring it back this summer. Downtown Pittsfield, Inc.( DPI), Tito’ s Mexican Bar & Grill, and WANDER hosted the new series on select evenings on Liberty Street( the alleyway between Tito’ s / WANDER and Crawford Square). Depot After Dark featured DJ-led dance parties from 8 to 11 p. m., with food and drink available for purchase.
ONLINE EXCLUSIVE
Read articles on Neon Newt in Becket and Hexagon Bagels in North Adams at berkshiremag. com, where you can also find our listing of LGBTQ + businesses.
NICK BURCHARD
Cross-collaboration runs through everything. The businesses network together through the Massachusetts LGBTQ Chamber of Commerce. The geographic proximity wasn’ t planned; it evolved.“ It just kind of organically happened,” Santangelo says.“ We all ended up in this little area together, which is kind of cool.”
As Santangelo puts it,“ If you imagine it, we’ ll make it happen.” The magic is that there is no single plan, just a continuum of ideas that keep widening the circle of belonging.
He describes WANDER in its current iteration as a wheel with spokes— a hub. Its location and the other businesses on North Street are near public transportation, putting it within easy reach of both South and North County. The gravitational pull didn’ t come without groundwork. Santangelo credits city and regional support as essential in WANDER’ s early stages. Staff at the PERC( Pittsfield Economic Revitalization Corporation) loan program helped him navigate available funding. When permitting complications arose in the building’ s older structure, the mayor stepped in to help move things forward.
“ I reached out to them day one,” Santangelo says of the organizations that include Downtown Pittsfield, Inc., 1Berkshire, and others.“ The minute I signed that lease and the space was completely empty, I went right to the city. I said,‘ I know nothing. Help