Originally Posted by
Dogwood
Good late Sept early Oct Fall hike choice well suited for you for a two wk east coast jaunt. As you may already know the lower 100 miles or so of the LT conjoined with the AT is easier. That 100 miles isn't as steep, as rooty, isn't as rocky, is generally wider tread, and largely but not entirely routed through deciduous woods. In the northern 2/3 or so the LT goes steeply at times only a pedestrian can follow directly up and over the state's highest peaks. Don't expect easily graded switchbacks as you find in Colorado such as on the CT that is constructed for multi use. The construction is based on straight up and straight over the peaks. Come ready to hike. All the LT elevation profiles I've seen can be deceptive as that northern half has so many 50 ft or less elev changes that don't show up on the profiles. I suppose you're going SOBO?
I've found the same thing as Orthofingers said particularly in late Sept after a strong growing season and a bit lax of maintenance on the ski runs: "As far as "walk right down a gentle ski run and hit a resort" I've done that and I was shocked at how difficult that can be. Most ski runs from the top of the lifts on that section (where the LT goes) are anything but gentle. What seems like a gentle slope with snow on skis can be much more steep walking. Also, a ski trail that can take you a few minutes to ski top to bottom can take much, much longer to negotiate on foot. But the biggest challenge for me, and one that I had not thought about was hiking through chest-high, thick grass on the slopes. I must have fallen ten times from getting my legs tangled up in the grass (which was actually kind of fun because the grass was so cushioning, you couldn't get hurt)." I'll add some ski runs have loose rocks some the size of basketballs.
Getting back to your question though yes you'll be able to supplement a bit so possibly can afford taking less food at times.
VT has to be one of the friendliest hitch hiker states for hikers. Only in the most touristy areas will you have a harder time finding a hitch from tourists or those from out of state(Naw Yarkers, Bostonites, hoity toity Connectites, etc) with second homes in VT. Vermonters know about their beloved Long Trail. When they see you they will know what you're doing being a hiker hiking the LT and needing a ride. Many times these same folks will stop and offer or ask what you're doing to confirm you're hiking the LT which opens the door to getting a ride.
If you're getting off before Killington Ski Resort and didn't already do it on your AT/LT hike you may want to take the tram up to the observation deck where there will be some food and possibly a hot chocolate, beer , etc at the Upper Summit. It's a great panoramic view on a clear crisp fall day.