The Appalachian Trail and the Chesapeake and Ohio Canal Towpath are both accessible from here and offer two very different types of hikes.
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.
Rutland is an excellent destination as there are many hiking options available. I researched several but haven't actually done them all, hopefully you will find something that meets your needs. An out and back is obviously possible in any direction and can give you full control over the desired distance/time, but I find the point to point routes more compelling.
I have ridden most of the long-haul Amtrak trains except the Zephyr, so I started looking there. My departure point (also the terminus) is Emeryville, CA. First, could I get there by the 9:10 am departure time using public transit? It would take two hours and forty minutes, but it could be done.
I have driven over ten thousand miles in the last two years to hike and camp in beautiful places across the US. The car spent days sitting at trailheads, baking in the sun, soaking in the rain, and consuming money (when it was a rental) and gas the rest of the time. A car does have many advantages but it is not low impact or traveling light. It felt like my base weight was sixteen pounds plus another three thousand for the car; it left me wanting for a better way. Could I backcountry hike and backpack around the US with literally just the pack on my back?