Windsor Trail

This classic trail from the 1930's is the most direct (i.e. steepest) assent up Mt Ascutney. The bottom half follows a brook, with one tricky water crossing and plenty of water for dogs most of the way. About 20 minutes up from the start, hikers will come to Gerry's Falls, a little rest spot with a beautiful waterfall. It goes by the old stone lean-to shelter, which is worth seeing, especially since it has a spring for fresh drinking water. There are a few views, but not many. The trail is interesting with flora in the summer and fall foliage. It's a significant hike in snow, but I know a couple 70-year-olds that made it, so it is definitely doable!