Police Chief Michael Wynn points out the police station to Hodari Cail.
PITTSFIELD, Mass. — Mayor Linda Tyer led a tour around downtown Pittsfield for members of the governor's staff Thursday as the two administrations "start a dialogue."
State Community Affairs Director Hodari Cail joined a cadre of local officials and business leaders to see some of the highlights of Pittsfield's downtown revitalization efforts over the last decade or so.
Tyer led the tour that brought the group to the likes of the Berkshire Museum, Hotel on North, Barrington Stage, the Colonial Theater and even the parking garage on Columbus Avenue.
"I was hoping to highlight that Pittsfield is in an evolution. We've started to move away from being a GE town and moving toward our future, which really is being led by a new generation of young leaders and new ideas," Tyer said.
Through nearly two hours in rainy weather Thursday, Tyer pointed out the renovations of the former fire house into the 1Berkshire offices, the current condition of the police station, and the success arts and culture have had in turning the downtown around. Through a series of public and private partnerships, the city invested in a number of those buildings to drive the arts and culture economy.
"We can replicate that in other parts of our city. We still need the state's help with building out the William Stanley Business Park. We need help with funding for our garage which is important for our downtown. We want their support when we start talking about a modern law enforcement community in terms of a modern facility," Tyer said.
North Street is in its final stage of reconstruction and the Colonial, Barrington Stage and Beacon theaters have been up and running for a number of years. But, there is still work to be done downtown. The group stopped at the Columbus Avenue garage, which has 200 parking spots that support the businesses on the northern end of North Street.
Director of Maintenance Dennis Guyer said the structure is failing and beyond repair. There are plans to replace it with a 400-space garage to increase available parking downtown. But, to do that, the city is going to need the state's help.
Cail considered his trip as the start of a relationship between the state and the city. Gov. Charlie Baker is in his second year of office while Tyer is three months into her first term.
"I think the first thing is dialogue. I think before you can have any impact you have to really take an interest in what is going on, No. 1. No. 2, you have to really start the conversation about what communities need and how you can help," Cail said.
"I think the most important step is having that dialogue, accessibility, and that's what we are trying to do here."
He said Pittsfield's investment in the downtown "speaks volumes" to the city's push. He cited the museum as being impressive with its size and long-term plans. And he was amazed by both the arts events and the education tied into the cultural institutions. He said it all goes into having "an area to work and play."
"What I do is give my report on what we did, what we saw, and make a recommendation on how we can help the people in the Berkshires," Cail said.
Tyer said there will be a number of projects the state could help with in the next four years. She chose to lead a tour showing off the successes Thursday rather than in areas like the William Stanley Business Park, which are on the radar for redevelopment.
"I wanted to give them a reason to believe that their investment is worth it for the community," Tyer said.
Cail said his next step is to arrange a visit from the governor to see for himself what's happening in Pittsfield. Cail said Baker is "hands on" and staff will be there to assist the city in a number of ways.
"We just want to make sure we are helping in anyway we can," he said.
Joining the tour were state Rep. Tricia Farley-Bouvier, Police Chief Michael Wynn, Downtown Pittsfield Inc. Board President Jesse Cook-Dubin, City Council Vice President John Krol and Berkshire Chamber of Commerce President Jonathan Butler. Along the way, the group discussed the history and relevance of the various investments made in the downtown and ultimately the results.
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Friday Front Porch Feature: This Luxury Home Has Plenty of Amenities
By Breanna SteeleiBerkshires Staff
LENOX, Mass. — Are you looking for a big house to enjoy your days with a big movie theater, a sauna, and more? Then this is the house for you.
Built in 2004, this seven-bedroom, and nine-bathroom home is 7,073 square feet on more than an acre. The home comes with an elevator to the lower level to access a theater, sauna, gym, wine cellar, massage room, and its very own soda fountain.
The home also has a guest house with a saltwater pool. A multi-car garage greets you with heated floors.
The this home is listed for $4,950,000 and is located in the 125-acre, gated Pinecroft compound.
We spoke to Leslie Chesloff, the listing agent with William Pitt Sotheby's.
What do you think makes this property stand out in the current market?
Chesloff: This gated Berkshire stone estate truly redefines luxury living in the Berkshires. What sets it apart is the rare combination of resort-style amenities and complete privacy. The property offers Canyon Ranch-level wellness living with a full spa experience at home — including a sauna, massage room, and gym — plus an eight-seat hi-def theater with wine cellar for entertaining. The heated, gunite saltwater pool and spa are complemented by a fully equipped pool house with a guest suite and complete kitchen, perfect for extended family or guests.
What was your first impression when you walked into the home?
The moment you step inside, you're struck by the quality and craftsmanship — those 300-year-old reclaimed timber floors set an immediate tone of authenticity and warmth. The scale is impressive but never overwhelming; this is a home designed for gracious living, not just show. The natural light, cathedral ceilings, and thoughtful flow between spaces create an inviting atmosphere that balances grandeur with genuine comfort.
How would you describe the feel or atmosphere of this home?
This home feels like a private wellness retreat meets sophisticated family estate. There's a serene, spa-like quality throughout — enhanced by features like the sauna, steam shower, and massage room — but it never feels clinical or cold. The Berkshire stone exterior and reclaimed timber floors ground the home in a sense of place and permanence. It's designed for people who appreciate the finer things but want to actually live well — whether that's screening a film in the eight-seat theater with wine from your own cellar, hosting poolside gatherings, or simply unwinding in your own spa sanctuary.
What kind of buyer would this home be ideal for?
This is perfect for the discerning buyer who values wellness, privacy, and culture in equal measure. I envision someone who spends their days hiking or exploring the Berkshires, then comes home to unwind in the sauna or pool. They might entertain guests in the theater wine room, host multi-generational gatherings with family staying in the pool house guest suite (which has a full kitchen), and appreciate being minutes from Tanglewood, world-class dining, and Berkshire arts.
This could be an executive looking for a primary residence with work-from-home flexibility (there's an office/bedroom suite), a wellness-focused family, or empty nesters who want to host adult children and grandchildren in style and comfort.
What would you say to a buyer trying to imagine their life in this space?
Picture Saturday morning: you're sipping coffee on the terrace overlooking your heated saltwater pool, planning a day at Tanglewood. Your guests are making breakfast in the pool house kitchen — they have their own private retreat but are steps away when you're ready to gather. Evening arrives, and you screen a favorite film in your eight-seat theater, selecting a perfect bottle from your wine cellar. This isn't just a home; it's a lifestyle that brings resort-level wellness, entertainment, and hospitality to your doorstep — all within a secure, maintenance-free compound where nature meets luxury.
Are there any standout design features or recent renovations?
Absolutely. The home includes an elevator for multilevel accessibility, which is both practical and forward-thinking. The lower level is exceptionally well-conceived — a true entertainment and wellness wing featuring the eight-seat hi-def theater, wine cellar, sauna, gym, massage room, and even a charming soda fountain. The gourmet kitchen has been recently updated, customized wet bar, while outdoor living is elevated with the heated gunite saltwater pool/spa, firepit, and that incredible pool house with guest suite and full kitchen. Also, new HVAC system and heated driveway.
Thoughtful details like cedar closets, steam showers, central vacuum, and backup generator show this home was built to the highest standards.
You can find out more about this house on its listing here.
*Front Porch Feature brings you an exclusive to some of the houses listed on our real estate page every week. Here we take a bit of a deeper dive into a certain house for sale and ask questions so you don't have to.
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