We Played Connect 4 by Travelling to Actual US States

I think both groups really overlooked the midwest. Minnesota especially has a TON of options. It's got a super funky shape which means it has sections that are North, south, east, and west of several states. Like a few of the other states, the "main" city has the big airport which has lots connections galore. 

Depending on how your rules are working you can pick which state is "on top" of another which opens up lots of options:

A vertical line at at 96° 37W passes through N Dakota, S Dakota, Minnesota and Nebraska OR Iowa,

ND -> MN -> SD -> IA
ND -> MN -> SD -> NE

or 
MN -> ND -> SD -> IA
MN -> ND -> SD -> NE
MN -> SD -> IA -> NE
ND -> MN -> SD -> IA

Horizontally you can chain together , 

MN -> SD -> MT -> ID
MN -> SD -> WY -> ID
MN -> SD -> WY -> MT 
MN -> ND -> MT -> ID 

The middle flat states have lots of potential too (although not as interesting for challenges lol)

KS -> NE -> MO -> IA is really compact 

I think my route would have been 
a) fly to Des Moines
b) drive to Lincoln if not blocked (otherwise pick up Missouri, Kansas, and Minnesota)
c) drive to Topeka
d) drive to Jefferson City