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Is this itinerary doable?

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I am trying hard to see if we have enough time to see some fall foliage, towns, waterfalls, etc. I REALLY need your advice if this itinerary is possible:

1.Arrive Boston/Logan airport Thursday Sept. 27th approximately 11:00 a.m.
2. Drive to Jackson, N.H. - stay 1 night (?) - see Mr. Washington, do Cog R.R. visit North Conway etc.
3. Leave Jackson on 28th (?) head N. on 302 to see Crawford Notch, head south to Lincoln, spend night in Lincoln .
4. Leave Lincoln on 30th (?) head back to Boston via I-93
5. Flight home from Boston on October 1st approximately 8:00 p.m.

We can add another day to the trip if advised.

Would it be best to stay somewhere between Lincoln and Boston over night and then head to Boston/Logan airport mid day on our "flight home" day.

I desperately need help.

It was easier for me to plan 2 trips to Ireland in 2009 and 2010 than it seems for me to figure out when, where, and how long to make this trip to see fall foliage.

Thanks!

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