|Resident overseer of the NY Metro AT train station:|
The only place you can catch a train directly from the AT (only on weekends) -
NY highway 22 near Pawling
Nuclear Lake, near Poughquag, NY to Jug End Road, South Egremont, MA (just west of Great Barrington), 75.1 miles
General Impression/Theme: Upscale neighborhoods and towns. This entire section of the AT (starting at Warwick, NY and extending up to Cheshire, MA) passes through exclusive, high income areas with palatial homes and large estate-like tracts. The trail towns are packed with high-end shops and restaurants, while things like laundromats are scarce.
People: 'Wisconsin', Mech. Engineering Student who has spent the last three summer breaks doing the AT. This year he finished the trail, accomplishing the northern third of it despite being hit so hard by Lyme Disease that he couldn't hike one last mile to get to Salisbury (his Dad came to the rescue). 'Day-Glo' and 'Bluebird', a married couple hiking a big section from Del. Water Gap to North Adams, MA. Steve 'Salty' Wilkinson from Graysonville, MD, and 'Peanut Eater', transplant from England, living for the last 35 years in LA, both on successful NoBo thru-hikes.
Supply/Overnight: IGA at Kent, CT; Salisbury, CT; Trailhead Parking Lots; Great Barrington Holiday Inn Express (20% hiker discount) and grocery stores.
Worst Memory: The downside of upscale: spoiled kids, underage drinkers, carrying their contraband up to vista points along the AT, drinking, and leaving all their trash on site. There were some pretty trashy places through this section, and perhaps a shortage of volunteer trail guardians and maintainers.
Best Day Hike: My favorite is the remote section beside the Housatonic River (no roads this side of the river) between River Road, just north of Kent, CT and Cornwall Bridge, CT. The trail runs right along the river with constant pleasant views. Another excellent shorter piece of riverside walking on the Housatonic is the popular section from Bulls Bridge south to Tenmile River.
A very close second (it was hard to choose) is the hike that parallels Undermountain Road near the CT/MA state line. Park at one of the two side-trail Trailheads on that road (CT/MA 41) and hike the Undermountain trail to the AT, cross Bear Mountain, CT with its stone monument and excellent view, Sage's Ravine with its wonderful roaring stream and waterfalls, then back up to the precarious cliff-edge walk along Race Mountain, affording constant excellent views to the east. Then hike back down to Undermountain Road via the Race Brook Falls Trail, or do the whole thing in reverse. You can also access this section from the west, parking in the Guilder Pond Day-Use parking area, but be sure to get in and out before the gate closes. I gave this hike 'runner-up' status simply because it's a more common type of AT scenery (a summit, an exposed ridge walk and a walk beside a roaring stream) than the Housatonic river walk.
Finally, I highly recommend the hike past Rand's View and the Giant's Thumb (a significant natural standing stone). Going up to it from Falls Village, CT, you can also take in the handicapped accessible loop of trail southward alongside the river, and visit the Great Falls of the Housatonic.