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Kelan O'Brien, chair of Berkshire Pride, speaks about Jahaira DeAlto at the Pride flag-raising event at City Hall on Wednesday. Pride Month in the city was dedicated to the murdered transgender activist.
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Members of the district attorney's office pose at the event.

Pittsfield Raises Pride Flag, Dedicates Pride Month to Jahaira DeAlto

By Brittany PolitoiBerkshires Staff
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Mayor Linda Tyer proclaims Pride Month.

PITTSFIELD, Mass. — Pride Month in Pittsfield has been dedicated to former city resident and transgender activist Jahaira DeAlto, who was murdered a month ago in Boston.

"Jahaira was an original founder of pride, she helped start the first Transgender Day of Remembrance here in the Berkshires and she helped set the foundation for the LGBTQ-plus community to organize here for the first time," said Kelan O'Brien, chair of Berkshire Pride, at the Pride flag-raising event at City Hall on Wednesday. "We have always been here. She provided that foundation."

The city of Pittsfield in partnership with Berkshire Pride raised the LGBTQ-plus flag in honor of Pride Month with a large photo of DeAlto, who worked with local victims of abuse, prominently displayed at the podium on the steps of City Hall.

A crowd of local and state officials and residents cheered while the flag was raised to "I'm Coming Out" by Diana Ross. This has been a yearly tradition since 2017.

Mayor Linda Tyer delivered the proclamation for Pride Month in Pittsfield.

"This image of Jahaira right here is so powerful, I know we are all deeply saddened and grieving for what she has left us. The legacy that she has left us but the image of her in this photograph is powerful. And I feel her presence with us today just by looking at this image here in front of the podium," she said.

"[The city] honors the LGBTQ-plus community's courage, compassion, creativity, recognizing the social, economic, and cultural contributions they make to our community, including advocating for the equal rights of all people speaking out against intolerance and discrimination and helping to break down the walls and fear and prejudice within the city."

Berkshire County resident Najwa Squailia spoke on the hypocrisy of "pride capitalism" and the many elements that encompass pride.

"More anti-trans bills have become law in this country, young trans people are being denied life-saving medical care and yet, in that same moment those same children can walk into Target or into a local craft supply store and find a vast altar of rainbow covered accessories and appeasement perhaps that they accept gratefully what little protections the culture has to offer," she said. "But an invitation to joy and celebration is an empty gesture unless it is paired with the most basic human rights."


Squailia said transgender children -- like all children -- deserve more than the current conditions that exist within our country.  She highlighted the "tremendous figures" in tax dollars allocated for guns and missiles when food insecurity and the need for mental health and social services are their highest.

"Pride is the Black trans women with black, indigenous, and queers of color who have paved the all too bloody ground for our rainbow-colored festivals. Pride is in the radical acceptance of oneself. Pride is knowing that all bodies are good bodies. Pride is in Tulsa. Pride is with the Palestinians in the West Bank, Gaza. Pride is against Asian hate. Pride is immigration," Squailia said.

"Pride is sex work. Pride is disability. Pride is neurodiversity. Pride is against Orientalism and fetishization of the other. Pride is against mass incarceration. Pride is against the exploitation and appropriation of favor. Pride is in these too little, too late colonial reparations. Pride is in the mutual aid that does not wait for recognition or legitimacy from the cultures, dominant narratives, but comes from love."

State Rep. Tricia Farley Bouvier, representatives from the District Attorney's Office, Ward 1 Councilor Helen Moon, and Councilor at Large Pete White were in attendance at the mid-day celebration among other officials.

O’Brien said there will be no Pride Festival in the city in June but the organization will be supporting Berkshire NAACP on Juneteenth holiday -- June 19 -- which is the day the festival would typically be hosted.

Berkshire Pride reportedly will be holding a rally on June 26, the day that Supreme Court in 2015 held that states may not deny marriage licenses to same-sex couples.

The organization is exploring festival options for later in the summer or closer to National Coming Out Day on Oct. 11.


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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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