Pittsfield is an option I have explored but haven't hiked. Most of the posts from here on will be potential future trips as I try to document all the opportunities I find and gather them in a single resource.

How to get there

  1. Amtrak CHI to PIT (~18 hours) Departs: 9:30pm, Arrives: 4:30pm

Directions to the Appalachian Trail from PIT

  1. From the Amtrak station
  2. Walk to the Intermodal Center for the bus
  3. Take the Hinsdale #4 bus to Park Ave & High St ($1.75, 1-2 hour layover then ~30 minutes)
  4. Walk (0.2 miles west) to the Gulf Road Parking lot trail head

Various Hike Options

North Bound

North bound options are discussed in the Rutland post and cover:

  • Pittsfield to Bennington, Manchester, Rutland, Waterbury, White River Junction and the ways to reconnect with Amtrak

Appalachian Trail South

  1. Pittsfield to Peekskill (MA-8 and 9-Dalton to US9 NY403-Peekskill, NY 160 miles)
  2. Walk NY403 to Garrison (north west) to catch the Hudson Line train (~3 miles)
  3. Garrison to Poughkeepsie ($6.50 (at station, $13 on train), ~40 minutes) Departs at 3:02pm, Arrives: 3:40pm
  4. POU to CHI (1.5 hour layover then ~19 hours) Departs 5:10pm, Arrives 10:12am