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Need help planning USA trip - autumn colours and more

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To get over my post holiday blues I have started to think about my next trip. I would like to come to the USA, in particular the east coast to see the autumn colours and also I would like to see Savanah and perhaps Charlestown. My lovely friend Sue has also asked me to visit her in Portland Oregon with a side trip to Seattle.

Like Australia the distances are huge and I need help with driving vs flying and which direction I should follow.

Research has told me the colours are anywhere from last week in September to 3rd week October and that year by year this is changing. I am thinking of flying into Portland first then heading to opt 1) Seattle, then Savanah and working my way north. Would I then fly from Charlestown to Vermont? For some reason I fancy Vermont. Or opt 2) Portland, Seattle, Vermont then south. Should I add Boston? And of course have always fancied Montreal and or Quebec.

I would be looking at no more than three weeks total. I have looked at an Inn to Inn walking tour, has anyone done this? I am very open to suggestions as it it early days. Hardly over the jet lag!

Can anyone give me some help? Would driving from Charleston to New Englad be too far for that time frame?

Thanks in advance
Schnauzer

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