A pretty walk through the woods to the summit of Wachusett Mtn, crosses the auto road near the top.
Cross the street from the parking area and head uphill. You will shortly cross the Bicentennial trail. This trail goes uphill and can be wet near the bottom if there has been recent rain. Mostly dirt path with some rocks in the wetter areas and as you get closer to the top. Keep an eye out as you go up the trail for big boulders and interesting trees.
This is a nice peaceful route, though there are no facilities where you start and may or may not be any maps. Check the visitor's center out for these.
Views mostly at the top - great place to stop for lunch. Boston skyline, Mount Monadnock and Mt Watatic are visible from the top on a clear day.
Rt 140 to Mountain Road (signs for Wachusett Ski Area). Go past the ski area and the DCR Visitor's Center at the top of the hill (though you might want to grab a map and a pit stop here). As you head down the other side watch for the parking area on the left side of the road at the intersection with Gregory Rd.
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