The Berkshires Blog

The Berkshires Best-Kept Sledding Secrets – Berkshire Family Focus

sleddingLooking for some free family winter fun this winter? I’ve got a local secret that involves rope tows and hills of all sizes. Look outside. Do you see nothing but the fluffy white stuff? Then it’s a great time to partake in one of the Berkshires most inexpensive winter family activities — sledding.

*A quick note before I go any further: Please check with property owners before sledding at all private venues.

Now that that’s taken care off, let me share a little about the fun to be had from Williamstown to Great Barrington and beyond for experienced and non-experienced sledders alike this winter.

One of the area’s best little kept secrets (well not anymore), is the hill at Osceola Park (Osceola Street) in Pittsfield. What’s so special about this hill? It’s got a rope tow. Yup, each Saturday and Sunday from noon to 4 p.m. you and your little (and not-so-little ones), can get help with the trek to the top of hill with this baby. The tow experienced a few electrical problems during the projected opening weekend, but the City of Pittsfield has been diligently working to fix the problems. For more information about the state of the rope tow visit the Pittsfield Parks and Recreation Facebook page at P.S. The park also has a skating rink this year, courtesy of the Pittsfield Fire Department, so be sure to bring your skates along, too, for a full day of winter fun.

Some other Central Berkshire favorites include the hill at Clapp Park and Reid Middle School in Pittsfield; Wahconah Regional Country Club and the tubing hill at Bousquet ($15 for two hours; ages 5 and up).

Other Southern Berkshire sledding hill favorites include Monument Mountain Regional High School in Great Barrington and Bartholomew’s Cobble in Ashley Falls.

If you are heading to the Northern Berkshire area, sledders have been spotted every year at the Taconic Golf Club in Williamstown and the Forest Park Country Club in Adams. There is also an extra large, steep hill that provides the perfect sledding opportunities for experienced sledders at Sheep Hill on Cold Spring Road in Williamstown. But this isn’t a hill for the sledding novice, so be sure to accompany young children — and the folks at Sheep Hill ask that you please do not build jumps on the hill.

So get to it. Bundle up and head out to the local hills for some free (and low-cost) sledding adventures. And once again, be sure to call ahead for permission to ski and to check out the conditions of the hills.

For more recommendations for sledding hills go online to