I’d suggest that you think about using rail transport to get most of the way. I’m sure I don’t need to tell you about Amtrak from D.C. to NYC (fairly straightforward) but it gets a little more difficult to find the needed information from there, though the travel itself is not hard. The MTA runs the Metro-North Railroad system out of NYC (specifically, out of Grand Central Terminal just a bit north of Penn Station in Manhattan where Amtrak comes in) into most parts on New York State. The line you need is the Harlem Valley line (the same one the famous Appalachian Trail Station is on, which you would have passed last year south of Kent, assuming you were NOBO.) I’d suggest taking it to Wingdale, NY and then either getting a trail shuttle to take you to the trailhead or a taxi to take you to Kent (or the trailhead.) You can then get a shuttle to the town nearest wherever you get off-trail, catch a bus either back south to Wassaic, NY (the end of the Harlem Valley line) or to another nearby major city the has Amtrak service (Albany, NY is the obvious choice here.) That way you won’t have to worry about a car, the trip won’t actually take any longer than driving, and you’ll arrive ready to hike rather than exhausted from a very long drive.
I know this sounds like a lot of work, and it does take a bit of planning, but it is worth it. I did something similar last year on my second section of the season by taking New Jersey Transit trains to NYC, then a bus out of NYC directly to the trailhead on NY17a (just south of Wildcat shelter) and heading north. I would have taken a Short Line bus back to NYC from Bear Mountain Inn, but I was injured and had to cut my hike short. But even then, I managed to get off-trail at NY17, call a cab to take me the 1 1/2 miles north to a Metro-North station (Harriman), and trained it all the way back to Philly (I didn’t even have to go into NYC, but changed to a New Jersey Transit train at Secaucus Junction.)
Once you get north of New Jersey it becomes a relatively easy matter to get to or near the trail by using public transit. I highly recommend this for anyone not actually from the area, as most of the info you need (for bus and train stops and schedules) is online, and you can put together a pretty good itinerary ahead of time. I also tend to carry printed timetables for the lines I’ll be using and any others that I might be near, for exactly the kind of emergency I had on my NY hike (I cracked my shoulder blade in a spectacular fall on Arden Mountain and had to walk out 1 1/2 miles to NY17, including descending the Agony Grind.) Seriously, though, the public transit route is the way to go.
Here are a few links to help you on the way:
The ATC “Getting to the Trail” page, including the all-important shuttle list. Be careful with this info though, it is sometimes a bit dated so be sure to check before relying on it.
The Metro-North Railroad page, which will give you the timetables and ticketing for getting to Kent.
Peter Pan Bus Lines They run most of the bus service now in western MA and upstate NY, which they took over when they bought Bonanza Bus Lines. They have regular service between most MA trailtowns in the south (places like Lee or Dalton, your likely end-points about 100 miles north of Kent) and Albany.
Amtrak Just to make the list complete, though I’m sure this is one you already know about.
Those should get you started. I hope all goes as planned and you have a great hike.
Strategic