Worldpilot, I did a similar routing a few years ago (from Hampton, NH, 40 miles from your Bedford MA).
If you would like some recommended stopovers / lunchbreak stops, let me know and I can elaborate.
What aircraft will you be flying? I've flown in to Oshkosh twice VFR, and it's as easy as chips (don't forget to download and read the NOTAM when it gets published, on or around 1st May. [the 2013 version is
here if you would like to see the general idea].
Russ.