B y L i a m G o r m a n
Jesus Is King. May you repent and worship the lord.
A World of
Wander
JAY SANTANGELO
JAY SANTANGELO HAS CREATED A WELCOMING SPACE FOR ALL AT WANDER BERKSHIRES
It’ s been said, not all who wander are lost.
For Jay Santangelo that is mostly true. The road to owning and operating Wander, Pittsfield’ s newest cafe / event space / soon-to-be educational darkroom, has been long and winding— tragedy, marathons, coincidence, sobriety, and photography have all led Santangelo to this point.
“ I tell people that I followed the breadcrumbs,” says Santangelo.“ I don’ t want to say it was an accident, because once it came to my mind of what I wanted to create, it’ s been done with a lot of intention.”
And what Santangelo has created is a warm, safe, sober, LGBTQ + space, welcome to all who want coffee, pastries, sandwiches, conversation, art, crafted mocktails, music, dance parties, film screenings, but most of all community— everything Santangelo, a relatively recent transplant from Austin, Texas, was looking for when they came to the Berkshires.
“ I say all of Wander exists because it was a selfish need,” explains Santangelo.“ I was providing a space for myself, a third space, a safe space, a brave space as I am a transgender, queer individual myself. And so I was like,‘ Well, if I wanted it and needed it, then other people might, too.’”
Located at 34 Depot Street in Pittsfield, the front entrance to Wander is nestled down an alley behind Tito’ s Mexican Grill. The former home to Berkshire Running Center and Brew Works years before that, Santangelo has transformed the 3,000-square-foot location into a space that is simultaneously spacious and cozy.
A custom bar welcomes those in need of caffeine and nourishment— handcrafted coffees, herbal teas from local herbalists, non-alcoholic drinks like Kombucha, house-made syrups.“ Everything is made from scratch,” says Santangelo.
Further in, curated nooks filled with eclectic furniture and design combinations create small spots in what otherwise might feel like a warehouse.
“ It ' s kind of like different little lounges,” says Santangelo.“ I tried to break it down but keep it very open so you could have conversations in different areas and still see everybody without necessarily having to sit on top of them.”
Adding to the ambience is the industrial feel brought with exposed brick, large windows, and the low rumble of trains passing through the Pittsfield Train Station.
At one end of the room are clothes racks from Berkshire Trans Exchange, loaded with free items for those in need of gender affirming clothing. At the other end, in the far corner, sits a piano that will soon be maintained by Berkshires Jazz and will be center stage at the end of April as the Pittsfield Jazz Crawl concludes at Wander for a dance set.
While music is part of the event programming, including Misty Blues doing their Gospel Road House Revival in May, much of what will be happening leans towards the LGBTQ + community and creating a space where people can feel safe.
“ It ' s serendipitous timing to have this space for people to where they can come and feel safe and feel like they are not alone, and then feel empowered and bring joy, you know?” Santangelo says.
The spot has become so popular, Santangelo has recently expanded their hours to include more evenings.“ People want a space just to come that’ s open at night that ' s not a bar. That still has that feel, that nighttime ambiance. And you ' ll think you ' re in a bar or club, depending on the evening.” While it is a sober space, Santangelo does allow alcohol for private events.
Born and raised in Boston, Santangelo is a veteran of the hospitality industry— first spending time in the back of the bakeries their mother worked at and owned, then
102 // BERKSHIRE MAGAZINE Holiday May / June 2023 2025