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Sledding Destinations in Berkshire County

By Sabrina DammsiBerkshires Staff
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The snow is perfectly packed for a day of sledding. Head for the hills before the winter season ends. Here is out list of sledding destinations: 
 
Have a sledding destination that we missed? Email info@iberkshires.com and we will add it.
 
Clapp Park
Pittsfield
 
Every year Berkshire County residents can be seen flocking to Clapp Park, sleds in hand, to experience the thrill of sliding down the hill. 
 
It’s no surprise children drift to this park in the winter. Many can be seen sliding down the hill with cardboard during the other seasons. 
 
The packing snow adds the perfect amount of slippery to slide down the bumpy hill and the right amount of soft to catch riders when they inevitably roll into the snow. 
 
The hill has a few sliding areas varying in bumpiness and height, so it is a great destination for parents looking for a place to take their youngsters. 
 
Don't have a sled? No worries, the park has a sled library so visitors can borrow one. 
 
After spending an hour or so sledding, warm up and have a cup of hot chocolate at one of the money restaurants in downtown Pittsfield. 
 
Sheep's Hill 
Williamstown
 
Enjoy a ride down a hill while overlooking Mount Greylock. Sheep's Hill at Williamstown Rural Lands is one of Williamstown's most spectacular properties open for passive recreation and has community programming on natural history and rural heritage.
 
The entrance is on Cold Spring Road, about 1.2 miles south of Williamstown center. Parking is available off Route 7. 
 
Monument Mountain Regional High School 
Great Barrington
 
Berkshire County has many mountains and hills, it is no surprise that even our schools have magnificent hills to sled down. One of the most noteworthy hills is Monument Mountain Regional High School. 
 
Trails made by eager children and teens can be seen in the hill in front of the schools and as soon as those schools bells ring students can be seen racing for a chance to experience the hill's thrill.
 
Reid Middle School
Pittsfield 
 
Reid Middle School mimics this joyous scene with the tracks from the sleds being seen on the side of the school greeting the children. 
 
The hill is mildly steep and open making it an amazing sledding destination. Students bundle up head to toe and release their stress with joyful screams as they speed down the hill.  
 
Osceola Park
Pittsfield
 
The weather is lovely for a sleigh ride together through the steep hill at Osceola Park, located at 41 Osceola St. Children can be heard yelling woohoo as they zoom down with their friends and family. 
 
Wahconah Country Club 
Dalton
 
Wahconah Country Club is used for golf in the spring and fall but in the winter the landscape is perfect for sledding. 
 
The bright screen grass becomes a winter wonderland filled with screams and laughter as kids and their families slide down the hills, some brave enough to make jumps. 
 
More information on the country club here

Bas Ridge Golf Course
Hinsdale
 
Bas Ridge Golf Course is a family run public golf course in the heart of the Berkshires with some of the best views of the Berkshire Mountains. 
 
In the winter the 18-hole course becomes a winter wonderland of snow. The hills of the grounds makes it one of the best destinations in the area to make lasting memories with your family this winter season.
More information on the golf course here
 
Forest Park Country Club  
Adams
 
Forest Park Country Club is yet another golf course that is transformed into a land of joyous screams and snowy trails for the excited children eager for a thrill.
 
The nine hole golf course is located at the base of Mount Greylock provides a scenic view of the mountains as you bolt down the hill.  
 
More information on the country club here
 
Commercial Tubing Options
 
The county also has commercial tubing options at local ski resorts including Bousquet Mountain and Ski Butternut. 
 
Bousquet Mountain
Pittsfield 
 
Bousquet has a dedicated tubing hill for ages 5 and up with a magic carpet, making your thrill seeking a little easier. Tickets are $30 each for an hour and a half of tubing. More information here
 
Ski Butternut
Great Barrington
 
Ski Butternut features a 7-lane tubing park for family fun. The Tubing Center is located on the  far-left side of its main parking lot with its own ticketing building. It now offers hundreds of tubes, and a magic carpet lift,
 
Tickets are $30 each for an hour and a half of tubing. Children must be able to ride in tube alone. More information here
 
Honorable Mention Outside the County:
 
William Cullen Bryant Homestead
Cummington 
 
The Trustees of Reservations serene vista William Cullen Bryant Homestead is a wonderful sledding destination that has pastures, fields, and woodlands to explore. 
 
The two-story-farmhouse-turned-three-story Victorian cottage served as lifelong inspiration for editor and publisher of the New York Evening Post William Cullen Bryant who summered there during his childhood. 
 
From its iconic red barn to an elegant allée of maples, this lovely home is testament to the celebrated poet's ideal of living mindfully on the land.
 
More information here

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If you would like to contribute information on this article, contact us at info@iberkshires.com.

Fenton: Governor's Council Must Deliver for the Berkshires

Community submissionGuest Column
I am a Springfield lawyer running for Governor's Council and I am asking for Berkshire County residents to support me over an incumbent from North Adams. 
 
Here's why: Last year I learned about staffing issues in our regional courts that I could not ignore. In 2025, it was reported that four of Western Massachusetts' 11 Superior Court judgeships were vacant, all at the same time. A few weeks later, that grew to five vacancies. This meant there were only six Superior Court judges serving all of Western Mass at a time when Berkshire, Hampshire, Franklin, and Hampden counties had more than 100 pending homicide cases. 
 
Those numbers were alarming to me, so I started to engage with leaders in the community who work most closely with the court system and I came to learn that these vacancies were only the tip of the iceberg here in Berkshire County.
 
I learned that no Superior Court or District Court judge had been appointed from the Berkshires since the current incumbent took office. As a result, there is not a single Superior Court judge who lives in the Berkshires today, and several of the District Court judges drive in from other counties to support Berkshire courts in Pittsfield, Great Barrington, and North Adams. Court staff also informed me about severe staffing shortages at the Berkshire Clerk of Courts office resulting in other counties needing to loan staff to the Berkshires just so hardworking employees can take a brief and planned summer vacation. This is not normal. These issues are a reflection of genuine problems with the Berkshire County court system and show a lack of proactive attention from our Governor's Councilor.
 
Instead of focusing on regional equity, I watched as the current incumbent celebrated that she has voted against the governor's nominees more than any other councilor, without much explanation as to why. Most recently, she voted against two extremely qualified former prosecutors for the Parole Board. This was despite an in-person plea from the governor and a letter of support from all the three of the district attorney's from Western Mass. Those votes do not show independence or standing up for principles, they demonstrate naivete, and an unwillingness to work with the key stakeholders.
 
I had seen and heard enough. I decided to jump in the race and challenge the incumbent to address these problems head-on.
 
I am a partner of a regional law firm. I understand our courts and the importance of having qualified, fair and hardworking judges. And I know how important it is to have judges from the Berkshires serving the Berkshires. To achieve that, you need strong relationships with the legal community and local stakeholders. You need to know how to use the power of the Governor's Council to fight forcefully for our region. And you need to be laser focused on identifying vacancies before they occur so that they can be filled quickly with local candidates.
 
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