I took the blue blazed trail that leads right down to the Inn at Long Trail. I didn’t really try to hitch into Killington since it was a short walk from the trail. There’s not really a town but there’s a great general store with decent resupply, great sandwiches, and alcohol. There’s also an outfitter another .2 down the road. You could do a short resupply here if you need to.
Hitching from here to Rutland was super easy even during the pandemic. Just wear your mask. Overall a really cool stop.