October's the time for outdoor autumnal activities. In Tom's case that means traveling to Long Island to tour wineries, go pumpkin picking, visiting a corn maze and running into Arnold Schwarzenegger in Manhattan. In Tim's case that means going to the Bronx to walk around a cemetery at night with a bunch of elderly people, which of course leads to a debate about the reality Michael Jackson's Thriller video is set in.

This week Tom recounts his recent trip to Chicago and the midwest for the first time ever where he discovers how big lakes can be (really big), the numerous ways entrepreneurs are ripping off the Chicago Cubs, and lazy facial hair. Also the guys solve a listener problem concerning what type of gift is appropriate for a new "fauxmance's" birthday.

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