Start at the Lafayette Place Campground. Hike up Cannon Mountain via the Hi-Cannon trail then backtrack and hope on Kinsman Ridge trail going out over North Kinsman and South Kinsman. Turn around at South Kinsman and hike back until you get to the Fishin Jimmy trail. Take that down to the Lonesome Lake hut and then take the Lonesome lake trail back to the Lafayette Place Campground. 

Beautiful off road path connecting Breakwater Lighthouse in South Portland Maine through marshes, beaches, and forests to the Maine - New Hampshire State Line.  Part of the East Coast Greenway connecting Florida to Maine.

https://www.easterntrail.org/

Ragged Mountain is among the most popular hiking destinations in Connecticut, and over the past few years has become a trail running hot spot as well. This loop consists of a few miles of the Metacomet trail, one of the blue-blazed trails maintained by the CTFPA, and a connector trail blazed in the same blue with an additional red stripe. There is a popular Strava segment of this route from West Lane in Berlin, CT, traveling clockwise around the loop (362 attempts by 108 people at this time), but you can start and finish from any point on this loop and travel in either direction.