Chris Byrne over at The Anarchangel points out that Don Draper's midnite dash from Westchester to Bedford, MA to drop off his new girlfriend's brother would've been a tall order. But who cares when my hometown of Framingham gets a shout out as a landmark! Don is hesitant to drop off the brother "20 miles from Framingham." I'd guess the writers wanted to punch up the phrase "middle of nowhere?" Right? That's what you'd normally say. "I can't just drop you off in the middle of nowhere."
20 miles from Framingham = Middle of Nowhwere
My best guess is that he was in Auburn, MA, having taken 84N to the Pike. Lovely place, Auburn.
And just because it's the best scene ever... The Carousel... "This device is not a spaceship. It's a time machine."
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