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Weekend Outlook: Festivals, Concerts, and More

By Sabrina DammsiBerkshires Staff
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Berkshire County has a variety of events this weekend including festivals, car shows, concerts, and more.
 
Lenox Apple Squeeze 
Downtown Lenox
 
Lenox Apple Squeeze returns this Saturday, Sept. 24, from 10 until 5 p.m. throughout downtown Lenox. 
 
This free event will feature live music, magic, kids carnival with hayrides, and more. 
 
Complete line up of events and locations found here
 
 
Freshgrass Festival 2022
Mass MoCA, North Adams
 
The Massachusetts Museum of Contemporary Art will be hosting its annual Fresh Grass Festival this weekend from Friday through Sunday. Thousands are expected to be in the city during the three-day event.
 
Live music will be performed throughout the grounds and at Joe's Field with headliners including  featuring Gary Clark Jr., Old Crow Medicine Show, Tanya Tucker andTrampled by Turtles. There will be plenty of vendors will be on site selling merchandise, food, and drinks. 
 
A 3-day adult pass is $174; see more on ticket prices and performance lineup here
 
 
Whitney's Farm Market & Garden Center
Whitney's Farm, Cheshire
 
It’s pumpkin season! Whitney’s Farm brings back its local favorite, Pumpkin Fest, this Saturday,
Sept. 24. 
 
Pick pumpkins, ride on a hay wagon, get glitter tattoos, walk through a corn maze, and more every weekend through Halloween. 
 
Open every Saturday and Sunday from 11 a.m. until 5:30 p.m. 
 
More information here
 
 
25th Annual Country Fair at Hancock Shaker Village
Hancock Shaker Village, Pittsfield
 
The village will be hosting its annual county fair this Saturday and Sunday from 10 a.m. until 5 p.m.
 
The event will feature local food, vendors, music, animals, craft beer and cider, dancing, an antique tractor exhibit, and more. 
 
More information here
 
Texas Hold’em Tournament
North Adams Elks Lodge, North Adams
 
The Adams Street Fair will be hosting a Texas hold'em carc event this Sunday at 1 p.m. to raise funds for Adams first responders. 
 
Buy-in costs $50 and re-buy is $25, plus high hand. For more information call Dennis Dunn at 1-802-688-7382 or email Haflinger4@verizon.net
 
More information here.
 
Sugar Hill Car Show 
Sugar Hill Assisted Living, Dalton
 
Sugar Hill will be hosting a car show this Saturday from 11 a.m. until 3 p.m. to raise funds for Sugar Hill Senior Living Activities.
 
Sugar Hill residents and people from the surrounding cities and towns can mingle with one another as they view a variety of different vehicles including antiques, classic, muscle, hot rods, and motorcycles displayed on its 18 acre property
 
Show car registration cost $20 and includes two free lunch tickets. Check-in starts at 10 a.m.
 
In the case of rain the show will be on Sunday, Sept. 25.
 
 
The Festival Latino of the Berkshires
Town Hall Green Park & Saint James Place Theater, Great Barrington
 
The Latino Festival of the Berkshires celebrates Hispanic Heritage Month this Saturday from noon until 6 p.m. 
 
This free event will exhibit the history and beauty of the Latin-derived cultures and will feature American folklore dance and music performances, language and cultural activities, artisans, and Latin cuisine vendors.
 
More information here
 
Black Legacy Project Film Screening & Concert
Berkshire Community College, Pittsfield
 
The Black Legacy Project will be hosting a free screening and concert this Friday at 7:30 p.m. to celebrate the year anniversary of the project's launch.
 
The will screen the Berkshires episode of the documentary series followed by a Black LP concert featuring local musicians, and will conclude with a talk back with Project directors and musicians.
 
More information here
 
Meander: Classical Concert
The Clark, Williamstown
 
The Clark Art Institute will be hosting a free meander-themed concert this Saturday from 2 until 5 p.m. 
 
Participants can roam the grounds to encounter performances by musicians and dancers in an effort to complement the "Tauba Auerbach and Yuji Agematsu: Meander" exhibit which will be on view through Oct. 16. 
 
More information on the event here
 
Drive-Walk-Bike-By Art Show
Various locations, Pittsfield
 
The third annual drive-by art show is this Saturday in Pittsfield from 2 to 6 p.m. (Rain date is Sunday, same times.) This event is free to all participants and community. All profits from sales go directly to the artist.
 
Artists will be displaying their works -- from sculpture and crafts to music and dance -- on lawns, driveways and porches throughout the city. Everyone is welcome to celebrate the city's creative accomplishments by driving, walking or biking to various locations to see and even buy art. 
 
This event is part of ArtWeek Berkshires and supported by The Pittsfield Cultural Council. Map out your tour with the list of addresses found here.
 
Lenox Farmer's Market
80 Church St.
 
The Lenox Farmers Market, located at 80 Church St., formerly the Cafe Lucia, will be open this Friday from 11 a.m. until 3 p.m.
 
Participants can peruse local vendors while enjoying food and listening to music. 
 
For more information visit Lenox's Chamber of Commerce page.
 
Sheffield Farmers' Market
125 Main St.
 
Open Friday from 3 until 6 p.m. at First Congregational Church located at 125 Main St. 
 
The market will feature healthy food and products from a variety of local vendors in an attempt to nourish the community by protecting "local small farms, land, bees, and economy."
 
For more information visit the market's website
 
Pittsfield Farmers Market
The Common
 
Powered by Roots Rising, the market is open every Saturday rain or shine from 9 a.m. until 1 p.m. through Oct. 8.
 
Each week the market will have fresh locally grown fruits and vegetables, along with meat, eggs, cheese, baked goods by local vendors. Participants can shop for flowers, and artisan goods while listening to music and participate in family activities. 
 
For more information, visit the website
 
Great Barrington Farmers Market
18 Church St.
 
The market is open every Saturday from 9 a.m. until 1 p.m. until the end of October.  
 
Every week there will be locally grown food, flowers, and plants along with other local vendors. 
 
For more information, visit the website
 
Lee Farmers Market
Town Park, Main and West Park Streets
 
This market is open every Saturday from 10 until 2 p.m. It accepts SNAP/HIP, Senior Coupons, WIC coupons, and offer market match. 
 
More information here.
 
North Adams Farmers Market
St. Anthony Municipal Parking Lot
 
The market is open every Saturday from 9 until 1 p.m. into October in the parking lot across from St. Elizabeth's Church.
 
More information here
 
Williamstown Farmers Market
 
Spring Street, Williamstown
 
The market is open every Saturday from 9 a.m. until 1 p.m. into October in the parking lot at the bottom of Spring Street. 
 
This year the market will feature returning and new vendors, including a fishmonger, knife sharpener, baker, chef, and much more. 
 
More information here.

 


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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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