I think that's an interesting sign of the evolution of Sam as a character. In season 1, Sam associated Hallowe'en with 'the family business' and he hated everything to do with that. Now he's a natural born hunter, and embraces the family business, I guess he's just learned to embrace Hallowe'en as well? Especially as it's him and Dean celebrating together.
Yes, Sam saw it as connected to "the family business" and the monsters they hunted. He didn't want the reminder. But now, he doesn't resist it anymore, and it frees him up to enjoy Halloween. It's especially great when he can celebrates it with Dean.
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Just my head canon!
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They're having so much fun with those pumpkins. :D
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