Quick notes:
According to my New England Ski Bulletin Board, The old-timers are predicting an earlier and quicker leaf peeping season do to the dry summer.
The aerial tramway at Cannon Mountain, NH will be closing for an unknown period starting October 28th.
A number of ski areas in the region run a chairlift on weekends during leaf peeping season. At many, you can get off, walk around and ride or walk down later. I'm partial to the single chair at Mad River Glen as it goes base to summit and drops you at the Long Trail of the Appalachian Trail. Amazing views. Full disclosure I'm a co-op shareholder at MRG.
If you want to keep an eye on the leaves I suggest looking at the webcams of various ski ares. They're all here It VT, North to South: Jay, Burke, Stowe, Mad River Glen, Sugarbush, Killington, Stratton, Mount Snow.
If you want a rainy day activity, the King Arthur bakery, store and baking school in Norwich, VT is a lot of fun. There's also the Ben and Jerry's factory tour.