9 ½ mile loop hike - Mattabesett Trail and Lone Pine Trail - Guilford and Madison, CT
Trail Map - Guilford's Northwoods Trail System
Heading west from the parking lot, the trail starts off with a bang – a very steep climb up Bluff Head. The main trail climbs almost straight up to the 720’ crest, but there’s a side trail (blue blaze with orange dots) that takes an easier route up the hill. Your choice – 300 yards straight up, or 1 mile zigzagging up the side. I had almost 10 miles to go, so straight up it is! Complete with warning signs from CFPA noting it's a bad idea to fall from the ridge!