- recent - | Massachusetts Skiing Conditions Many people drive through Massachusetts on their way to go skiing up in Vermont, New Hampshire, or Maine. But there's definitely fun skiing to be had right here in Massachusetts - and you don't have to drive very far to get to it! Nashoba Valley Bolton Very small!! This is for practice runs, maybe, and even then there isn't much slope to practice on. Good for after-work if you can't make it to Wachusetts or another real mountain. Nashoba Valley Otis Ridge Otis Otis Ridge is on the small side, but is great for weekday practice so you're primed to go up to the larger slopes on the weekend. Otis Ridge Wachusett Mountain Princeton This is the closest to us, and a second favorite even though it's relatively small. Usually the trails are a bit icy and there are obnoxious snoboarders that enjoy running down skiiers. On the up side, there are all sorts of trees here, including "old growth" trees. We tend to ski Wachusetts once a week in season. Wachusett Mountain Breakthrough on Skiis A fantastic book No matter what your current level! Tweet