its legit. The Bike Film Fest has been growing steadily for the last few years, expanding to more and more cities. A new sponsor (42Below) wants to get recognition, develop a brand image as they begin to distribute their product stateside. The total costs they will spend on the ride is most likely comparable to putting up a few billboards and doing open bars at parties.
I have toured cross country before with a friend - I can't image what it would be like to go with 20 others. That said, it's sure to be a fun time for those that get to go. If the jerseys are well made, what's the big deal about wearing one with a logo? Any touring cyclist knows the first thing you forget to pack in your panniers is your self-awareness and concern for looks.