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Since you mentioned late Oct, I'd suggest using that car and going to Salem, MA for all their witch trial Halloween fun. On the ride you'd get to see the fall foliage of peak color in New England (I've been told it's last week of Oct though the leaves are already turning, so I'm not convinced 100%).
Are you driving from NYC to Boston? I'd suggest going the southern route through CT and stopping at Mohegan Sun or Foxwoods (I prefer Mohegan as it's so pretty inside) for some good food, bars, shopping, and I also think penny slots on silly animated machines are fun. I can make $20 last for about 3 hours there!)
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::: waiting for someone to post in Irishpipes 2013-2014 chapter listing thread that quota was .25 ::: - ASTalumna06
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