Hi everybody!

I've hiked VT, MA, & CT on the AT, in their entirety, as well as half of NH, & half of NY. I've also hiked the entire Long Trail, & the original MMM Trail (half of which is now the NET) three times in it's entirety (which is scary because there are old sections in the middle of MA that are almost completely impassable). Enough pleasantries, though. I have some real questions about Massachusetts, & Connecticut.

I'm planning a section hike that would either start at the Metro AT stop in Pawling, New York, & end at Mount Greylock in North Adams (Northbound), or the opposite (Southbound). My concerns lean heavily on mail drops (as well as elevation gains).

I understand that this could take between 2-3 weeks, & don't want to carry excessive amounts of food.

Which would you anticipate as the easier option? Starting in Massachusetts, & hiking south in the direction of Pawling at an elevation gain that slants downward, or hiking north, & ending in North Adams, at the cost of a much steeper elevation gain? I have found it harder to find my legs when I start at a steeper elevation gain, but the options for a mail drop seem more readily accessible if I start in Connecticut.

Cheers!