Join Date: Nov 2003
Location: Toronto, Ontario
Bikes: True North tourer (www.truenorthcycles.com), 2004; Miyata 1000, 1985
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It looks like it could be a very nice route, especially if you take the ferry boat across Lake Michigan. I don't know anything about riding across Michigan, but once you cross into Ontario (maybe via Marine City, but possibly Windsor or Sarnia), you should be fine.
You will want to get onto the Waterfront Trail quickly, although some of the rural roads between towns and cities could be quite interesting. I can tell you that the Waterfront Trail that runs east along Lake Ontario from just East of Toronto all the way to the Québec border is excellent. There are marked bicycle trails most of the way, and you will be able to avoid heavily trafficked roads 80% or 90% of the time.
Once you enter the province of Québec, you will be following the La Route Verte much of the way to Québec city, although I think you may need to get to Montréal to pick up the trail. There are others on this forum who are much more familiar with this leg of the journey, and hopefully they will chime in.
There should be no problem flying home from Québec city. It is a decent sized airport, and I had no significant problems flying in and out, other than the normal hassle of flying with a bicycle. Taking the train is also a good possibility, although I doubt you could get all the way home easily. No problem going from Québec city to Windsor, which shares a border with Detroit.
If you do this trip, remember that you will need a passport to return home. Americans can enter Canada without a passport, but the USA has become fanatically strict about keeping out the bad guys. No matter. If you don't already have a passport, having one is a, well, passport to adventure!