York at NantucketThose who know me know that I am a simple man with simple loves. I love cookies. I also love road trips. So as the end of 2003 approached, I decided to leave a high-paying job with Yahoo! to pursue a non-paying amalgamation of my loves, the Cross-Country Cookie Crusade.

My favourite cookies at the time (yes, the significance of the past tense here shall be soon revealed) were Pepperidge Farm’s Chocolate Chunk Cookies, which (my fellow cookie aficionados will know) are named after various charming locales throughout America: Tahoe, Sausalito, Sedona, Nantucket, Montauk, and Chesapeake (Sanibel and Stowe arrived on the market later.)

Being brilliant (and I continue to believe that I am brilliant, despite rapidly mounting evidence to the contrary,) I thought that, if I went to each of these places and photographed myself with the appropriately-named bag of cookies, that surely Pepperidge Farms would see the awesome marketing potential and gladly sponsor my road-tripping adventures. The Cross-Country Cookie Crusade’s advertising campaign, with its online blog, chats, photo ops and video spots, would be a coup for the folks at PF corporate, for the unbelievably low price of a few thousand dollars in gas and motel bills.

And over the course of the next 10 weeks and 20,000 miles, I delivered on the dream.

York at Tahoe

York at Sausalito

York at Sedona

York at Nantucket

York at Montauk

York at Chesapeake

I sent off the pictures, along with a well-reasoned explanation of how the Cross-Country Cookie Crusade was going to revolutionize how Pepperidge Farms did business, and several weeks later, I received their reply, which you can see by clicking here.


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