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Expecting a snow day? These are the 15 best places to go sledding in the Berkshires

With a day off from school, you'll want to hit up at least one of these Berkshire hills for nonstop sledding fun

Snow Day

The conditions at the top of the hill at Clapp Park in Pittsfield were perfect for a sledding day Oct. 30, 2011. 

When it comes to finding the best place to go sledding, there are three key factors to keep in mind: steepness, length of run and accessibility. 

Or at least, these are the factors Nick Watroba, a Pittsfield resident and co-founder of 413Shirts.com, says are the things he looks for in a good sledding spot. Last year, his mom gifted him a snow tube for Christmas, which inspired him to set out and sled down 28 hills in 28 days

Because of the short snow season last year, Watroba was unable to complete his mission, he said, but he plans to pick up right where he left off this season. 

"The snow melted at the end of February last year, and I never made it to 28 hills in 28 days," he said. "So, the upcoming tagline to the new videos will be, '28 hills in 28 days ... we just never said 28 days in a row.'"

Of the hills he was able to conquer last year, these were his top three picks:

Most accessible: Clapp Park in Pittsfield.

"It offers easy parking at the base of the hill with a fun, but safe, hill slope," Watroba said. 

Best advanced hill: Sheep's Hill in Williamstown; parking off route 7.

"The hill is so long and so steep that they have a rule where there can be no jumps, because it would be too crazy. It's great for 12 and up if someone is looking for a next-level ride," he said. 

Family friendly: Forest Park in Adams.

"This is a golf course in Adams. A windy road takes you through the course, where there are many hills to choose from. Small slopes for the little ones, and fun steep ones for the bigger kids."

Watroba went on to say that, ultimately, the best hill, really, is any one that you can find, whether that be in your back yard, a neighborhood park, or even the Lanesborough Target parking lot

The most important thing, he says, is to get out there and have fun.

"Sledding doesn't need [to be] a long drive; it's great exercise and it gets the fun flowing."

So, if you find yourself with a good amount of snow, warm snow gear and a sled or tube ready for the slopes, here are some places around Berkshire County to check out:

Forest Park sledding in Adams

Children sled at the fourth hole at the Forest Park Country Club in Adams.


• Hoosac Valley Elementary School

14 Commercial St, Adams

Forest Park Country Club

• 41 Forest Park Ave., Adams


• Wahconah Country Club

20 Orchard Road, Dalton


Lucy Rosen, 5, of Lenox, sleds down the hill at Monument Mountain High School in Great Barrington, where families joined to go sledding Dec. 26, 2017.

Great Barrington

• Monument Mountain High School

600 Stockbridge Road, Great Barrington


• Lee Elementary School

310 Greylock St. in Lee


• Tanglewood parking lots

The hill opposite the Main Gate of Tanglewood (West St., Route 183)


Clockwise from left: Erik Thomas, officers David Lemieux and Kyler Cahoon, Amalio Jusino and Kingston DeJesus, 8, slide down the hill at Southview Cemetery on South Church Street in North Adams, during a community sledding event. Thomas and Jusino organized the event, which they first held in 2013. 

North Adams

• Bryaton Elementary School

20 Barbour St., North Adams

• St. Joseph Cemetery

Church St., North Adams

• Southview Cemetery

Church St., North Adams


People enjoy a day of sledding at Osceola Park in Pittsfield.


• Clapp Park

233 W. Housatonic St., Pittsfield

• John T. Reid Middle School

950 North St., Pittsfield

• Osceola Park

41 Osceola St., Pittsfield


• Cole Field at Williams College

Stetson Road, Williamstown

• Sheep Hill

671 Cold Spring Road, Williamstown 

• Taconic Golf Club

19 Meacham St., Williamstown


Simon Shin slides down the hill at Taconic Golf course in Williamstown in 2017.

Jess Gamari can be reached at jgamari@berkshireeagle.com.

Digital content creator

Jess Gamari has worked at The Berkshire Eagle since 2016. She was previously a Berkshires Week intern in 2013 and a North Adams Transcript summer intern in 2009.

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