Williamstown MA South or Killington VT North Which way should I go?

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Strummystick

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I'm hitting the AT next week for a two week section hike. Last summer I did an end to end of the Vermont Long Trail and so I'm planning on adding to the 100 AT miles that were completed on that trip. That means I can go south from Williamstown MA (and hit the Berkshires right away)or north from Killington VT (with a bit of a hike before I enter the Whites ...if I reach them) Which way do you think I should I go?
Some of my personal goals would include ... meeting some interesting AT thruhikers, seeing some nice views without killing myself like I did in Northern VT, getting off the trail every 4-5 days for a day of playing and singing on my strumstick travel guitar (in some pretty touristy little New England town with shoppers who will toss $$$ into my hat). I had a great time doing that stuff in Vermont.
I tend to walk about 7-10 miles daily, so I'll probaly do a little more than 120 miles total. (I know that's wimpy but it's the hiking level that I enjoy, especially since I turned fifty last year!).
What do you think folks. North or South?
Strummystick
 
I would think that if meeting other interesting AT thruhikers is your goal, a southward bound section would be best, perhaps start in NH and work your way south to Killington, VT. I ran into a bunch of throughhikers in Williamstown, MA when I did the AT to Greylock. This was on 6/25 so surely you will run into many northbounders around northern VT...

Jay
 
Leaning toward the North

I'm starting to think that Killington North would work the best. I can do as many miles as possible and stop when I've had enough. On first glance that area seems to have fewer peaks until I hit the Whites. That,s the reason that I'm considering the Berkshires instead . I wouldn't want to just trudge through bug infested valleys for two weeks. Has anybody done that Killington VT Northbound hike in late July? Strummystick
 
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