One Week (2008)

From IMDb:

"Ben Tyler (Joshua Jackson) has been diagnosed with cancer. With a grim chance of survival in the best case scenario even if he immediately begins treatment, he instead decides to take a motorcycle trip from Toronto through the Canadian prairies to British Columbia. Along the way, he makes new friends, reevaluates his relationship with his fiancée Samantha (played by Liane Balaban), his job, and his dream of becoming a writer, and, after suffering some near-death experiences, learns to appreciate life.

Fitting squarely in the tradition of 'road trip' movies, the film features classic Canadian scenery, roadside attractions and Canadian icons: even the Stanley Cup makes a cameo appearance."

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