Growing up we always went to the WL town hall. Some decent sledding behind the building. Haven't done it in ages but it was always full of people any time it snowed.

I live in suffield and we go behind the academy/church/country club. I haven't had the cops called as of yet. But I'll come back to this post to see if anyone has any new ideas!

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Honestly, I have no idea if it's allowed. No one has said anything and people have definitely seen us. Sometimes other people are there too.

We went behind the WL town hall/library or Suffield academy.

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Perhaps try the Mill Brook Open Space in Windsor:

https://townofwindsorct.com/mill-brook-steering-committee/

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The location is a former golf course which is now a nature preserve.

Yes bell hill is the best spot

Just over the river is Enfield high school. It's got a great hill in the back.

There are some steep, if short, hills there. The trip would be fun, but brief.