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Exploring US & Canada December '12

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We're heading over to the States and Canada for Dec/Jan this year, planning to cover the West Coast then fly across to the East. It's going to be a cool experience- we're from tropical Queensland where 10 degrees c is a cool day! Would love some helpful tips for the itinerary we've put together so far!

Itinerary as it stands:
Arrive LA
Fly to San Fran (2 nights)
Fly to Seattle (or train to Portland, then Seattle) (2 nights)
~ any thoughts on whether Portland worth a stop? Is is better just to fly through to Seattle? (I realise it's a long trip by train)

Ferry to Vancouver (2 nights)
Fly Montreal, train Quebec (2 nights)
Return to Montreal via train, (2 nights)
Train to Toronto (4 nights) (daytrip to Niagara) (probably for Christmas Day)

I've read that the US doesn't celebrate Boxing Day, wondering if Canada does and how widespread the closures are if so- is it an ok day to travel?

Third leg is getting to NYC, is it better to travel East from Toronto or to go south via Lancaster etc.
I'm Wondering if the Amish/Mennonite communities are accessible via public transport during Winter.

Is a Niagara-Lancaster-Washington DC-Philadelphia route a worthwhile on via train?

We'd like to make it to NY for the 30 of Dec (despite the horrific price rises at hotels at that time of year!)... so is it realistic to cover all of these between the 26-30?

Any suggestions would be appreciated!
Thanks :)

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