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The World Series, Halloween, Austin City Limits Music Festival, pumpkin pie, ComicCon, Ironman and the NYC Food Film Festival are all reasons why Travel Channel is obsessed with October.

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Grand Cayman

As autumn brings cooler weather, we’re dreaming of somewhere warmer in the Caribbean, like Grand Cayman. In October, 1 lucky winner can enter to win a trip for 2 to this sunny spot to enjoy fun activities, including a swim with stingrays.

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