Principal Maggie Harrington-Esko thanked the class for its positivity as she completes her last year as principal. See more photos here.
LENOX, Mass. — Pittsfield High School seniors reflected on the school year and their time "under the dome" at Sunday's graduation ceremonies.
Principal Maggie Harrington-Esko welcomed families and the 159 graduates to Tanglewood, noting that this year is different as it's her last at PHS.
"I am so grateful to the class of 2025, thank you for your positivity you brought to Pittsfield High School. Thank you for creating and strengthening an atmosphere of inclusivity at our school. Thank you for being role models to our freshmen, and thank you for being such a bright light, not just in our building, but in the city of Pittsfield. You've shown up for each other in big and small ways. You've led with kindness, you've lifted people up, and you've made space for students to see, feel seen and valued," she said.
"You have made our school more alive and like a home, our home under the dome."
Harrington-Esko has been with Pittsfield high for 20 years and was made principal in 2022.
Class President Caroline Sherman told her classmates that it's time to make their own paths.
"I kept trying to find the right answer. The right thing to say. The right advice to give. But, the longer I dwelled, the more I began to realize, there is no one right answer. We are given advice all the time, 'travel while you're young, go to school, get a masters, go to community college, save your money, move somewhere new, follow your dreams, be responsible' and so on," she said. "It all contradicts itself which gets extremely overwhelming as I'm sure many of you know. The truth is, none of this advice is better than the other because it is all based on someone else's experiences. Now, it is time for us to listen to our own advice, and follow our own passions. ...
"I think that for me, and for many of us, that is the scary part because it also comes with sometimes choosing the wrong decision, and making our own mistakes. But isn't it exciting? My plans are different from your plans, and your plans might be different from the ones you had yesterday, but that doesn't mean that either of us are wrong. Every single one of us gets a chance to narrate our own stories. And not only do we get to write them, and someday tell them, but the best part is that we get to live them."
Class speaker Helen Makdisi spoke about the school year and what being a General means.
"Like the changes us graduates are about to experience, our school has had its own shifts and waves that we may not have anticipated. I may not agree with how our school has been depicted from the outside perspective, but they always say it's what matters on the inside anyways. As an insider, I don't need someone who's never walked through Pittsfield High's hallway to tell me what my school is or isn't," she said.
"I can't say I've never been frustrated with some of the decisions and actions surrounding our school, but what I can say is this; as a community, we have always gravitated towards resilience, how we support one another, adapt, and rebuild in the face of challenges."
Makdisi said she'd had the pleasure of being an insider at PHS, and that to be a General is to "cheer as loud as you can during a game or performance; to be a General is to laugh with your best friends during the one free day of advisory you all have; to be a General is to show up to serve your community on your day off of work; to be a General is to embrace what comes and goes."
Superintendent Joseph Curtis, presented the Karl Boyer McEachron Award to Caroline Sherman. McEachron, a native of Hoosick Falls, N.Y., was pioneer in practical applications of electrical engineering and spent the bulk of his career at GE.
"Caroline, you have distinguished yourself, not only through your outstanding academic achievements, but also through your deep commitment to your school community, your involvement in extracurricular activities and your vision for future in science, you represent everything. This award stands for curiosity, integrity, integrity, perseverance and purpose. And on behalf of the Pittsfield Public Schools and the legacy of Karl Boyer McEachron, it is my pleasure and privilege to present you with this year's award."
Sherman will receive a plaque and a $2,000 scholarship.
Class advisors Mia Albano and Ashley Paradis presented the diplomas and certificates; the band played "Our Kingsland Spring"; the chorus sang "Be the Light" and "Changes" and the orchestra played Sergei Rachmaninov's "Romance for String" from Symphony No. 2.
Then Harrington-Esko gave the order to turn their tassels and dismissed the Generals for the last time.
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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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