Hey Mr. Pete:
If I may be as so bold as to make a suggestion to you. Try coming West through Canada into Michigan using the Blue Water Bridge at Sarnia/Port Huron.
Once in Michigan, make your way across the state, and you have two ferry's you can use to cross lake Michigan.
The "slow boat" (about 4hrs) is the USS Badger out of Ludington MI, to Mantiwoc WI. The "fast Boat" is the lake Michigan Ferry(about 2.5 hrs) is out of Muskegon MI to Milwaukee WI. Just google lake michigan ferry and you will come up with the websites.
Your other option is to head north across the Mighty Mackinaw Bridge, and then take U.S. 2 all the way West. However the Mackinaw is not a good bridge if you are intimidated by heights, plus there is a grated section in the middle of the bridge that is tough to ride on...
However, the U.P. of Michigan has some great riding and scenery!
I'll be in Gillette, but I am not leaving out until 7/13.
2003 K1200RS/GT Options
Oh, BTW, I too am origianlly from Upstate NY (West Point area)