Los Angeles to Boston in August 2009

[abcwill]

Hi everyone!

My friend and I are planning a road trip from Los Angeles to Boston, stopping via Springfield, Missouri on the way. We are planning to take
1) the route 66 all the way from Los Angeles to Springfield, MO to Chicago,
2) then take the Oregon Trail (US 20) from Chicago to Boston.

On the first (1) leg of the journey above, we plan to drive straight through with only one night stop from Los Angeles to Springfield. On the second (2) leg, we are hoping to slow down, enjoy,and stop for a few nights and enjoy the sites along the way: the great lakes, buffalo ny, niagara falls etc.

Does anyone have any recommendations for interesting places to stop, particularly for the second Oregon Trail part of the journey, which will include Chicago, Ohio, Pennsylvania, New York, then Boston? Are there any alternative routes that might be interesting?

We are hoping to do the entire trip in about 10 days.

Thanks so much!

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Will