Boston to Niagara and back Oct 12-26

I am UK based and new to this, and would be grateful for some advice on how to plan a route. I have come up with the following and would welcome some feedback and ideas about how to improve this.

Start at Boston on to Albany, Niagara, Toronto, Ottowa, Montreal, Portland and back to Boston.

Google reckons 1338 miles and 23 hrs driving, is this to much in 2 weeks? On this route which are the best stops, and places to see? Do you need to book all accomodation in advance or can you find it at the last minute?

Welcome aboard the RoadTrip America Forums!

Have a look through these discussions that cover the US portion of your trip and this one for the Canadian part. Two weeks is quite sufficient to wander around this area and see a good bit of what it has to offer. The best and worst part of your planning is the timing. Those two weeks are the peak of fall foliage season, so everything will be beautiful. It will also be crowded as everyone hits the road at the same time, so yes, I'd start booking accommodations now if you know where you'll be.

AZBuck