Prospect Hill Park

Prospect Hill Park is a small mountain in Waltham, MA that used to be a small ski resort. There are a number of small trails branching off from the main road (that I haven't explored) and a dozen or so cookout areas (not sure if you need a permit, it kind of looked like people were arriving early to squat at a spot). There is a nice overlook by the old observation tower that gives a good view of Boston and Blue Hills.

Some links:

Prospect Hill park (~2.8 mi):
The full ride (~24 mi):

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