5. Man vs. Montauk
5. "Man vs. Montauk"
A Wilderness adventure. Can the Hamptons provide that? Better question: can a Hamptons yuppie survive it? Well we'd sure like to see him try. Taking things outside Montauk (it would obviously be called Man vs. Montauk for alliteration purposes) the North Sea Wilderness Trail looks pretty challenging. Good luck running in those boat shoes and rock climbing in linen pants. There's also the Hamptons Conservation. The Film Festival is over and the freshwater fish are swimming, boys. And we know there is plenty of wild in Quogue to give an out-of-towner plenty to work with for a series of self-survival. Let the games begin. [Photo via]