Want to win the election? Take my way, that's the highway, it's the best.
So I had a little fun and decided to make a superstate following the length of Route 66 (excepting Cook County to make this actually work). The results were 273-263 (I had to kill Delaware)
I made sure to not split any state, so I combined North TX/OK with KS, South MO with AR, north IL with WI (flipping it). North NM was added to CO, South CA to AZ. In addition, VT and NH were combined, and parts of DE were combined with PA and MD.
Thanks to major urban centers like LA and St. Louis, Route 66 is a Safe D state, worth 28 EVs. Hillary's margin was over 1 million votes (thanks entirely to LA county).
Other figures:
New Wisconsin is worth 24 EVs, and is also hugely Democratic.
Old Illinois is only worth 5 EVs.
North Missouri is also worth 5 EVs.
Arkansas+ is worth 8.
Greater Kansas has taken much of Oklahoma's population and has gained an electoral vote, growing to 7.
Lesser Oklahoma is only worth 4 EVs, and was hillary's 5th worst state in raw vote total.
New Texas has dimmed its margin to under a million, but the loss of Amarillo gets it to only 37 EVs.
South New Mexico is worth 4 EVs and is very narrowly democratic.
Greater Colorado doesn't gain any EVs.
New California falls to 26 EVs, but is deep blue.
South Arizona is worth 22 EVs.
Any other questions?
statefile