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Boston, Massachusettes
The historic, cobble stoned town looks beautiful come fall, letting you nip into bars for hot toddies, restaurants for clam chowder, and then drive out to the outskirts for scenic apple or pumpkin picking. 

As for more spooky-oriented events, there is the Ghosts and Gravestones tours, ImprovBoston's hilarious GoreFest production which is meant to be a faux TV reality game show, plenty of Halloween bashes, and a Rocky Horror Show dinner and movie event. 
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