Undermountain Trail, Bear Mountain, Salisbury, CT
See more in our guide to 55 Amazing New England Hikes.
This popular hike intersects the Appalachian Trail after about 2 miles. At the top of 2,316-foot Bear Mountain (the highest peak in Connecticut) is an old stone viewing tower.
Level: Moderate | Distance from Boston: 151 miles
Salisbury, CT, 203-788-7665, website.