Join Date: Aug 2007
Location: Ithaca, New York
Bikes: Felt Z80 road bike, Trek 7.2FX hybrid, Jamis Aurora Touring, Volae Voyager recumbent
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Posted this in touring but will repost here:
My suggestion: start in Montreal
, cut into New York State at Kingston Ontario (which is a wonderful small city) on the ferry to Wolfe Island then Cape Vincent -- the ferry rides are really enjoyable and incredibly scenic as you cross the St Lawrence -- then follow the Seaway trail down around Oswego along the southern shore of Lake Ontario -- this is a beautiful route, no cities (except Oswego, which is pretty small and easy to get through), in fact very rural, then you can either hook up to the Erie Canal towpath or follow the Adventure Cycling Northern Tier Route (which you can actually pick up north of Oswego), which takes you to Niagara Falls.
Cross over into Ontario, follow the Lake Erie Connector route of Adventure Cycling along the northern shore of Lake Erie, cross over into Michigan. The State of Michigan has available a wonderful set of cycling maps
for $5 each which cover regions of the state, and show trails, roads and how bikeable they are, etc., available online (link above). Go to Muskegon as mentioned above, take the ferry across Lake Michigan to Milwaukee, then bike south to Chicago.
This way you get to see some of the most scenic parts of the Great Lakes region east of Chicago, avoid for the most part urban areas, and this particular route also is not very hilly compared to say the route from DC or NYC to Chicago.