Sledding in Western Massachusetts

Hilltown Families > Winter Activities > > Q&As > Sledding

Photograph of two older children sledding together with text overlay, "Sledding Hills Western MA."
Over the years we’ve been welcoming recommendations for sledding hills across the region from our readers to help connect families with community-based resources. Check out these reader recommendations from our archives!
  1. Kelly recommends: Frog Hill in Grenville Park in Ware is a huge hill and great for sledding.
  2. Abbi P. recommends: The hill behind Pearl Thodes Elementary School in Leyden. Great variety of steepness, fun for all ages!!
  3. Jamison S. recommends: For an area filled with as many hills as North Adams, is, you may be surprised to hear that the best sledding in the Northern Berkshires is found at local golf courses. In Williamstown at the Taconic golf course, located on Water St. In Adams, at the Adams golf course. And lastly, Braytonville Elementary School has a great hill to hit as well, but that spot is usually pretty crowded.
  4. Andrea recommends: The sledding hill at Mary Lynch Elementary School (Springfield) on North Branch Parkway is great. The hill is steep and is a good distance from the road/parking lots.
  5. Sienna recommends: Osceola Park in Pittsfield has a rope tow for sledders!
  6. Cynthia and Mark recommend: We like behind Smith College, take Route 66 going to Westhampton, the hill is near the old State Hospital, on your right side heading West. It is also across from the Smith College equestrian barn…. this is a big hill and usually has lots of college kid – for the more adventurous kid. (Northampton, MA)
  7. Diana recommends: Southwick High School. The hill there is long! And no traffic to contend with!
  8. Kathleen recommends: I like East Mountain Country Club – have not been this year yet but in previous years it was great. (Westfield, MA)
  9. Kara K. recommends: Look Park (Florence, MA)
  10. Jara M. recommends: We love JFK (Northampton, MA)… There is enough room for everyone to spread out and it’s clear at the bottom of the hill (i.e,. no trees to dodge).
  11. Erika recommends: The hill behind Mary Dryden Memorial Elementary school (Springfield) is great. fun enough for little or big kids. Very few people there when we have gone, even on the weekends. Also, across the street, there is a great hill behind Cathedral High School.
  12. Cultural Pittsfield recommends: Clapp Park in Pittsfield is terrific!
  13. Robin S. recommends: GCC (Greenfield Community College).
  14. Sienna recommends: The Worthington Golf Course and the Bryant Homestead in Cummington, MA.
  15. Faith Ann recommends: Beacon Field, Greenfield
  16. Michael C. recommends: For my son, I took one of those small, round sleds and tied a rope through its handle. Then I pulled him on a flat, snow-covered surface. He had a blast.
  17. Kristen H. recommends: Behind the middle school in Amherst. Located on Chestnut St.
  18. Bob C. recommends: The hill behind the Rowe Elementary School is a blast! Young and old will enjoy it. Park in the parking lot after school or on weekends.
  19. Christa F. recommends: HCC (Holyoke Community College) is great for all ages. Depending on where you decide to start from you can have a very small slide down or a very steep slide. Our family really likes it.
  20. Susan W. recommends: Chester Elementary has a great hill for anyone up in the hilltowns.
  21. Amanda S. recommends: [There is a] great hill behind Stop and Shop in Belchertown – GREAT hill. lots of families. [Also] the hill at Crocker Farm in Amherst (Rte 116) – easy parking at the school.
  22. April A. recommends: There’s a great hill behind Stop n Shop off of Route 9 in Belchertown! Just turn onto George Hannum Rd and go straight. Vere right after you go under the little bridge and you’ll see the hill on your right!
  23. Jim S. recommends: Try the hill behind the school near the brewery in Williamsburg.
  24. Kristen recommends: Behind the middle school in Amherst on Chestnut St. Plus, there is within walking distance two more hills in fields of middle school and wild wood elementary school.
  25. Jamison S. recommends: For an area filled with as many hills as North Adams, is, you may be surprised to hear that the best sledding in the Northern Berkshires is found at local golf courses. In Williamstown at the Taconic golf course, located on Water st. In Adams, at the Adams golf course. And lastly, Braytonville Elementary School, has a great hill to hit as well but that spot is usually pretty crowded.

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