The Long Trail to Glastenbury Mountain is a 22.6 mile out and back trail located near Bennington, VT that features a river and is rated as moderate. The trail is primarily used for hiking, camping, and backpacking and is accessible from May until October.
a buddy and I did this in January 2014. We started at route 9 and snow shoed all the way in to the GOddard Shelter, and back out the next morning instead of the west ridge. It was EXTREMELY cold overnight with ambient temps below zero and wind chills around -30. In the morning we made our way up tto the top of the fire tower, then broke trail the whole way out. It was somewhat grueling and should not be taken lightly in the winter. Would have gotten five stars, except you don't get much in the way of views, and the AT blazes are very worn so trail finding in deep fresh snow can be interesting...