Head Start recognizes people and organizations that have aided it in its work providing quality early childhood care at its 60th anniversary fundraiser this month. The event was held at Rare 297 on North Street.
Head Start Executive Director Brett Random says the organization is facing challenging funding times and thanks the guests at the fundraiser for their advocacy. See more photos here.
PITTSFIELD, Mass. — Berkshire County Head Start held its inaugural fundraiser on Oct. 11 to mark the organization's 60th anniversary.
The national Head Start program has been supporting children and families throughout the country for 60 years; Berkshire County Head Start has been making this impact in the county for nearly 50 years.
The room at Rare 297 Steakhouse, located in Hotel on North, sparkled with diamonds, symbolizing the program's longevity, reflecting on the 60 years of sustained impact and resilience to challenges that come along the way, said Brett Random, Berkshire County Head Start executive director.
To Berkshire County Head Start staff, families, and community members, the program is more than just child care; it enhances opportunities for success by inspiring every child's love of learning by partnering with families, advocating for equity, and fostering a connection to the community, speakers said.
Like many federally funded organizations, Head Start is experiencing some challenging times and its work is currently at risk due to the federal funding restrictions aimed to limit who we can serve and how we talk about our work, Random said.
"Tonight, your support transforms lives, giving children the confidence and the success to flourish and that my friends is truly worth celebrating," she said.
Around 85 leaders, educators, parents, alumni, and community supporters attended the event dressed in formal black attire to reaffirm Berkshire County Head Start's mission by showcasing the experiences of its current and former students and families.
Each year Berkshire County Head Start serves at least 250 children and families across six sites in Great Barrington, Pittsfield, and North Adams.
"That commitment comes full circle when you learn that 31 of our 85 staff are past or present. Parents of Head Start," Random said.
The program's legacy is visible in the generations of children and parents whose lives have been transformed.
Imagine a child showing up to Berkshire County Head Start maybe a little nervous and shy. However, with support from the staff and programming the child blossoms, gaining confidence, curiosity and the tools to succeed, she said.
"Behind that child might be a family navigating challenges such as language barriers, work demands or limited resources. Through Head Start, those families find guidance, support and hope; lifting the entire family in the process," Random said.
Berkshire County Head Start offers mental health services, vision and hearing screening, parent resources, preschool education and nutrition services, all under one roof, plus affordable child care options for anyone inside or in between, public or public funded care.
Alyssa Sakowski, executive coordinator, provided a glimpse into the direct impact of the organization's Resources to Empower and Advocate for Children and Households (REACH) program.
Last year, a father enrolled his son in REACH, but just weeks later received devastating news — he had a form of malignant cancer and was given only six months to live, she said.
At the time he was the only one working because his wife had been home full-time caring for their son because they could not afford child care and faced other barriers.
Thanks to the REACH program, their son was able to start in Head Start's full-day classroom.
"That one opportunity changed everything. His wife was able to return to work, and for the first time, they could make ends meet without worrying about child-care costs. That stability allowed this father to stop working and focus entirely on his health," Sakowski said.
"He began an experimental cancer treatment — one that required time, consistency, and hope. Since then, his hospital stays have become less frequent, and he's beginning to feel stronger. He's not in remission yet, but he's fighting and he's grateful."
According to Sakowski, the father recently told them that what gives him peace is knowing his son is safe, happy, and thriving every day in the program.
"That's what Head Start does. It gives families room to breathe, rebuild, and heal. Because when we support parents, we strengthen children. And when we strengthen children, we strengthen our entire community."
Sakowski concluded with a recording of children demonstrating what they love about Head Start. Afterward, Random and Sakowski distributed awards to its "Head Start Heroes," those who have made this work possible.
Awards
The Investing in Tomorrow Award was given to three organizations: Berkshire United Way, the City of Pittsfield, and the Josephine and Louise Crane Foundation.
The Investing in Tomorrow Award recognizes individuals who have made significant contributions to the REACH program. Their financial support helps families facing systemic barriers gain access to quality child care and essential services, ensuring that those who might otherwise be overlooked receive the help they need.
Berkshire United Way Interim President and CEO Katherine von Haefen accepted the award on behalf of the organization.
"Early childhood centers are often like a safety net that wraps support around families of young children," she said.
She highlighted the longitudinal data that shows investments in high-quality early childhood yields a rate of return of up to 13 percent bottom line. It is not only a critical service but a smart investment in the future for each of us, von Haefen said.
Mayor Peter Marchetti accepted the award on behalf of the city. He emphasized the pandemic's impact on the nation and highlighted how the $700,000 in American Rescue Plan Act funds allocated to Berkshire County Head Start facilitated the development of the REACH program. This program helped address needs that were worsened by the pandemic.
The Josephine and Louise Crane Foundation was unable to attend the ceremony. The foundation was established by Josephine Crane to increase opportunities for residents of Berkshire County.
According to the program, Josie Greene, the foundation's president, said they appreciate Head Start's holistic and comprehensive approach and that it provides services at multiple sites in the region.
The Early Childhood Advocacy Award was given to state Rep. Tricia Farley-Bouvier.
The award recognizes those who have shined a spotlight on the critical work of Berkshire County Head Start and Early Childhood Programs everywhere, Random said.
"Your voice, your passion, your unwavering commitment, inspires us all to further serve more families and ensure that every child and parent has the care, support and opportunities they deserve," she said.
Berkshire County Head Start does "God's work and certainly the most important work," which was especially proven during the pandemic, Farley-Bouvier said.
She said many think of it as "extra" when in reality early education and child care are central to the economy and to families — families can't work without reliable child care.
"Looking at the children themselves, we know the future is brighter with high quality early education," Farley-Bouvier said.
Farley-Bouvier emphasized the need to rethink our approach to funding, suggesting that early childhood education should be viewed as fundamental rather than an "extra." She also highlighted the inequities in funding for early education based on geographic location.
"It's through the advocacy of my colleagues in the House and in the Senate, through people like [Random and von Haefen] that we bring the advocacy together. We bring a team together," she said.
"And do you know when we know we've won — when the teacher of a third grader is paid the same as a teacher of a 3-year-old [is when] we have won this battle."
The Heart of Berkshire County Head Start was given to longtime educator Dianne Amos, who began working for Berkshire County Head Start in 1970 as an assistant teacher and soon advanced to the role of lead teacher.
The award was presented by Education Site Manager Shana Shippee, who was once Amos' student and later her friend and colleague.
In her heartfelt speech, which earned her a standing ovation, Amos reflected on her many years with Head Start.
When recently asked why she had stayed with the program for so long, she realized it was because of her love for children, the exceptional teachers — both past and present — and the "golden issue" that the Head Start team follows every day.
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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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