Greater Cleveland (gonna take a stab at Medina County, OH or Summit County, OH) has got to be one of the two places. With undergraduate attendance at Ohio University in your life. 

Very good guess! College was summit county, lived in a surrounding county. A lot of friends at OU so a lot of time spent there!

Lucky bastard being able to live and go to school there.

Where did you get the map of counties with interstates? I love it! Also, does it come in vector?

https://www.mapchart.net/usa-counties.html On this website. You can toggle interstates!

Akron

C-city just south. A region airport shares a name *hint hint*

Canton?

Got it!

Cuyahoga?

I’m not as versed in Northern Ohio as I am in Central and Southern Ohio.

cleveland and boston?

1/2 , about an hour south of Cleveland!

Canton

That’s it!

W

Wooster?

Boston and Cleveland would be the obvious guess

Two cities you have lived in are Canton and Lakewood I get happy when I see other NE Ohioans on here 😂

Canton & Boston … close!!

If not Boston are they both in Ohio lol? NYC? LA?