Oakland Trailwalk is a 1.1-mile loop trail near Wilbraham, Massachusetts, generally considered an easy route that takes an average of 22 minutes to complete. The trail is a forest trailandoffers a pleasant walk through a “pocket” of preserved land in Wilbraham, with some portions featuring suburban views of houses and backyards. The trek is mostly flat, starting at 150 feet elevation with only minor elevation changes, except for a 40-foot dip in the middle of the western loop that is somewhat steep but quickly ascends back up. The trail is great for hiking, snowshoeing, and running, is open year-round, and is beautiful to visit anytime.