It's going to be past peak in the White Mountains by mid-October. I live in the Concord NH area and always think Columbus Day weekend is about the peak for our area although it's hard to tell. You'll probably find some suggested drive on Yankee Magazine's website. For that time period I might opt for a trip to Portsmouth NH (either MHT or Logan would be good) and a foliage cruise on the inland rivers. There's some very pretty areas around Portsmouth i.e. Exeter or north to Kittery Point. You won't get mountain views so it depends on what you want. Western MA would also be good, SW NH or southern VT also. Suggest finding a lodging and then deciding once you get here. It doesn't take long to drive further north if color is late or further south if it's early.

Last year wasn't very good for color. If you end up with bad weather, it would be a good idea to be somewhere where you can enjoy an alternate activity.

I agree with Dfrost on the approach. Pick one place to stay, and do scenic drives, or walks from there. Don't go too far north. Portsmouth would be nice. Maybe somewhere in southern New Hampshire, like Peterborough (near Mount Monadnock) would be nice.

One other option, as I suspect it will be near peak in the Berkshires, You could take the long, very pretty drive out on route 2 (the Mohawk trail), then stay somewhere in the northwest corner of MA. From there you can drive into Vermont, or down into the Berkshires depending. And there are lots of nice things to do on rainy days, like visit the Clark or Mass MOCA.

I've been going to the White Mountains in October ever year for more years than I care to admit, and usually aim for about a week sooner than that. If you can change your dates a little, I would stick with the White Mountains. Unless the rain is very heavy, we just proceed with our plans and find the scenery to be just as pretty.

since you're only talking about two days and I'm hoping you mean you fly out on the third day then I wouldn't really try for anything beyond southern New Hampshire or Vermont. I would make Massachusetts my main drive and even driving out to Northwest mass is going to take several hours.
Depending on what time your arriving in the morning into Boston it's going to take you somewhere around an hour to get your bags get into your rental vehicle and get on the road.
From there you could head north up to route to, picking it up around Lexington and Concord and then head west.
If you get a chance stop in Irving. There is a great antique store on the left that serves very good ice cream and then continue heading out towards North Adams.
If you get in early enough 8 AM or so, then you should make North Adams with no problem and I'd say year safe it making your reservations for there.
At this point you could look at what foliage is doing around you if the season is slow You Could Drive North on route seven up into southern Vermont. If you got to Manchester you could stop at Hildene which was Todd Lincoln's home and her gorgeous views from that historic property.
If this season is moving fast you could head South on route 72 Stockbridge which is where the Norman Rockwell Museum is and that is also a beautiful place to stop and drive through. If you drove East from there you could stop in the area of the Quabbin reservoir (Hartman's Herb Farm B&B is near old Dana) and that could be your second nights stop as you head back towards Boston. The next morning you could slowly meander your way back to Boston and hopefully catch a late afternoon flight home.
This is still a lot more driving than I would like you to do on vacation but when you only have two days to work with I think you'll find it to be a fun trip.
If you don't want to drive quite so far in you'd like to relax a little bit more only go out on route to as far as Fitchburg and then south into the Quabbin reservoir and spend the day exploring the lost village scenic byway and places like new Salem and Petersham Massachusetts.
here's an article from my fall foliage route page on new Salem http://new-england-foliage.com/journey-from-olde-salem-to-new-salem/
I hope it gives you some ideas and as of right now I think the fall is can the be splendid.
Jeff foliage

Thanks for the responses. These are a great help.
Our initial plan was to arrive early morning on Saturday in Boston and take an early morning flight on Monday back to SanFrancisco - but I am seriously thinking of adding another day (arrive on friday instead). Adding another day may also allow us to checkout some sights in Boston.
We dont mind pushing ourselves during trips, so driving around for 2-3 days is ok.

If you land in Boston, I think you should do a loop, Portsmouth, through southern nh and into the route 2 corridor back to Boston. If you would like a great hike that is one the way, climb Mt Monadnock, the summit is bald and the fall foliage views are very impressive. If the weather is bad either stay in Boston or somewhere on the coast (Portsmouth, Salem, Portland) so you can do some other stuff or you could stay in Boston. Hope this helps.

Hi,

Its 3 days before we fly into Boston and wanted to get suggestions from people based on current conditions.

The following is what I planned (thanks to the comments earlier to my question)

1. 14th : Drive out early from Boston
2. Cover south NH (Peterborough, Keene)
3. Cover south Vermont (Wilmington,Jamaica, Arlington,Bennington)
4. Stay the night at North Adams
5. 15th: Drive south to see the berkshires area
6. Mohawk trail
7. stay the night in Boston
8. 16th : Fly out from Boston

Looking at the yankeefoliage map, seems MA doesn't have peek color yet.
If instead I want to cover more of VT and less of MA, will there still be color in burlington, stowe, middlebury, manchester area - or will it past peek. I can still change my hotel reservation in North Adams and stick to entirely NH and VT during this trip.

General comments on the above itinerary are also be welcome.

Thanks

I live close to Stowe and foliage is past peak here now. This is a good site for current conditions/suggested routes in VT
http://vermontvacation.com/Vermont%20By%20Season/Fall/Current%20Foliage%20Report.aspx