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Rental Car Rally
Yes, it's every bit as cool as it sounds. A 60 team dash from NYC to Montreal using only rental cars (OK other cars are allowed too, but rental car use is encouraged). Entry is a paltry $150, but you're responsible for your expenses along the route. Buy-in does, however, include a huge blowout party on the night the rally ends. Also be sure to read the entire event site for some great comedy.
