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Sledding Destinations in Berkshire County
By Sabrina Damms, iBerkshires Staff
09:48AM / Saturday, January 21, 2023
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There's snow this weekend! It might be slushy but there's enough to pull out those sleds you got over the holidays. Head for the hills before it disappears again. Here is our list of sledding destinations: 

 
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 and 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. 
 
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

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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