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After receiving a $1 million budget increase the Police Department has been aggressive in trying to hire additional officers.

10 New Pittsfield Police Officers Complete Field Training

By Andy McKeeveriBerkshires Staff
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PITTSFIELD, Mass. — Ten new officers have finished field training and will be out on the road next week.
 
The city has been trying to build up the Police Department and spent this last year aggressively hiring. Ten officers had been put through the police academy and through field training, concluding on Friday, and there are another seven in the pipeline.
 
"That'll give us a little bit of flexibility to start thinking about some actual moves and realignment now that we'll have those 10 bodies in patrol," Police Chief Michael Wynn said.
 
Wynn has repeatedly advocated to bring the staffing levels up to 120, a number based on the population and call volume. In May, Mayor Linda Tyer pushed an agenda to add six additional officers to the force and the City Council funded that in the budget with a $1 million increase.
 
That brings the authorized staffing level to 99 as well as hires for vacant positions. By the end of the year, the department is expected to be at 95, as long as everything goes smoothly, and in the process of hiring four more.
 
"That's including the six positions that Mayor Tyer created for us, two of which were supervisor's positions. Depending on how you do the math, our actual strength today is 88. That's a little disingenuous because we've got trainees on the payroll but I don't count them because they don't have police powers. The actual number on the payroll is 95," Chief Michael Wynn said.
 
Ten officers are just now completing their four-month field training program. For half of that time, they are observing a veteran officer and the other half, the veteran is observing the new hire. The new officers have arrest power, so they can help during an emergency, but need to complete the field training before going on patrol solo. (That is why many have recently noticed more officers arriving at a scene - the trainee and the trainer are considered one unit.)
 
"Our field training program has evolved over a number of years. We stick to the national best practice standards as far as duration and content. That's proven invaluable. We get a much more prepared officer with the field training program," Wynn said. "Although it is a considerable investment, it is the right investment."
 
That had just ended with the new hires doing solo patrols starting Friday night and on Monday morning Wynn said a command meeting will determine exactly how to utilize them.
 
The chief expects the new officers wil boost the patrol unit, helping to offset shortages there, and free up specialists to perform other duties. Multiple years in a row the department has been overspending its overtime budget because of shortages in the patrol department. Those shortages have also led to specialty officers doing patrol instead of their specialty.
 
"In patrol right now there are seven units on the street. One of them is a K9 handler and one of them is a traffic specialist. They are not doing their specialty. They are answering calls as patrol officers. If we get through this expansion, the goal would be there would be seven units on the street plus a K9 handler and a traffic specialist," Wynn said.
 
He is also looking to add a few officers and a sergeant to the detective bureau, which he says has been understaffed for a year.
 
Long-term Wynn wants to build a traffic unit. Currently, there are only two patrol officers with traffic as their specialty. The first goal would be to leave them on patrol but not counting as part of the daily patrol numbers — allowing them to focus their time and energy in being proactive with traffic enforcement. He hopes by the end of the summer when the other four are done with the academy and field training, the department will create a dedicated traffic unit, including the hiring of a traffic sergeant.
 
Pulling the K9 unit out of the patrol numbers would be another goal but not likely to happen for a long time. By staffing up the patrol unit, the department will be "regaining capabilities" it had lost in just trying to maintain staffing.
 
Three additional officers will be starting the academy this week and four others have been in for the last two months. In August, the four are expected to be ready for solo duty and in December the other three would be ready. 
 
However, there will still be a gap and another round of hiring is needed. The department is now looking at all potential candidates. 
 
"We are so far down on the current list that we've actually requested a statewide list just to see if there are any candidates that might be workable between now and the new list," Wynn said.
 
In March a new Civil Service test will be administered and a new list generated. That list is expected to be certified in the fall. 
 
"We're a residency preference community so we are only allowed to look based on people who lived here at the time they took their test. We have to go through all of them first. Then, we get people who express interest in coming to the Berkshires and we get that list. We depleted those lists. So we asked the state to send us everybody in the state and we are trying to work through that list," Wynn said.
 
The entire process of hiring one officer takes about a year, Wynn said, while at any minute current eligible officers can retire, others could quit, and others could be fired. He says four officers will be eligible for retirement in the next year.
 
"This is a horrifically difficult system. Because we manage the Civil Service process to the best of our ability and we do detailed background checks, it is a cumbersome system. If we were in an active hiring process from the minute a candidate signs our list to indicate interest, it is a year before we can plan on them being available on the street. That's if everything goes right," Wynn said.
 
The $1 million increase in the budget has flipped the script, however, in that instead of waiting until a retirement to start the hiring process, the department can get the process going early in anticipation.
 
"If we didn't have that, we wouldn't be able to have these candidates in the academy in the academy. We wouldn't have had the vacancies. We wouldn't have had salary money until these people left. By having the additional salary money available, even though we are not going to see a net uptick toward that 120 for a while, we can start to accelerate the process which we have never been able to do before," Wynn said.
 
Wynn said for too long "we were looking in the wrong direction" when it came to staffing and the number dwindled. 
 
While today the number is 88 sworn officers, the actual number available for duty is 79. Five officers are currently out on injury while another four are unavailable for various reasons. Wynn says traditionally about 10 percent of the total number is unavailable at a given time.
 
Public safety is a top priority in the Tyer administration and one she campaigned heavily on. However, the city is facing financial troubles when it comes to the revenues and the tax levy so it isn't quite known whether the city will be able to increase the force above 99 in future years. As of Friday night, Tyer had not provided comment on the staffing of the department.

Tags: community policing,   Pittsfield Police,   

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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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