I participated to the International Air Rally last August. It started in Oshkosh, went up North to Iqaluit on Baffin Island and then back South to Charlevoix.
What a great experience. Some 20 planes participated. There were teams from France, Germany, Switzerland, South Africa, Canada and the US. The only problem was the weather... Nevertheless, All managed to maintain the schedule and return home safely.
If you have a chance, check next year's rally. The info is on the Web.