> Near the Delaware 896 exit on Interstate 95 in Newark, DE is
> a billboard for Sunny 104 FM in Philadelphia.
>
> This interchange is *40 miles* from Center City
> Philadelphia.
>
> Are there any other stations that rent billboards this far
> (or farther) from the city of license? Probably plenty.

> Especially if the COL is a large market.
>
> ixnay
>
Numerous Chicago stations advertise on billboards along I-94, just outside of Kenosha Wisconsin. One billboard that tends to get advertised a lot around there is for The Drive out of Chicago. It usually will say:
The Drive Now Loud & Clear on 96.9. Or you might find it saying 97.1 Fuzzy, Try 96.9 The Drive.
97.1 in Chicago is the only city grade signal that doesn't cover the entire market, so the station simulcasts on 96.9. licensed to Zion Illinois, which not only covers the northern suburbs of Chicago, but also Milwaukee & the south suburbs of Milwaukee. So The Drive billboards have been posted around Franksville Wisconsin too, which is outside of Racine, and I think once I saw one in Milwaukee County too around Oak Creek.