Have you used Wachusett Mountain?
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We love the learn to ski program offered at Wachusett! My daughter took several group lessons and it really help teach her the skills and build her confidence. She now loves skiing this mountain. I would say it is great for beginners. We have not experienced any issues during the pandemic, but we book the earliest reservation because it does get crowded.
A range of runs close to Boston that aren’t too crowded (at least from 7-11am). Ample parking. Just be careful driving there in the snow.
I've been going to Wachusett for a long time, but unfortunately this winter I had a bad experience there. The mask rules were not enforced at all, and the the lines for lifts were really crowded. We saw an employee knock over a sign that told guests to wear face coverings. Most upsettingly, a woman yelled & cursed at another skiier over a mask argument and none of the staff stepped in to deescalate.
499 Mountain Rd, Princeton, MA 01473