Shadowbrook is a 3 mile loop trail located near Richmond, MA and is rated as moderate. The trail is primarily used for hiking and is accessible from April until October.
This is a fairly short loop trail right off of a parking lot that overlooks a BEAUTIFUL lake. The trail is actually called Olivia's Overlook and can be found by walking from the parking lot through a small meadow to the trailhead (look for the carved rock - I forget the inscription but I believe the name on it is "Michael"). The path meanders through the woods and eventually opens up at the top with a view through a break in the trees out to the surrounding mountains. In the winter I'd imagine this view is pretty spectacular when some of the tree cover is gone. The hike itself is really just a quick walk with only 600ft of elevation gain. It's great if you have an hour to kill and want to get in a quick walk/run in the woods, but it's certainly not a "destination" hike. Very quiet too - we only saw one man and his dog doing a trail run to the top.