One of my favorite photos is on route 50, just east of Dodge City, KS (Ardell, KS). It's the first image on my home page of a grain elevator
http://www.lostamericana.com.
About 100 miles north of there is Monument rock (might be worth the drive if you have the time and you're getting clear skies for sunset & night photos).
https://www.flickr.com/photos/vincentjohnson/2267148720/in/album-72157603346855148/Dodge City has a new whiskey distillery called Boot Hill Distillery. If you're into that.
The drive from Lamar to LaJunta, CO. is beautiful. Make sure you have gas, long way between stops. If you find a dirt road going north through open range fields without any "no trespassing" signs, take a drive off the main road. The quite of the wind there when you get out of your car is almost zen like. Lodging in that area consider Garden City, KS, or Pueblo, CO. However there is a nice KOA (with cabins) in Cotopaxi, CO, right on the Arkansas river (good rafting nearby).
Hit Sweeties Sandwich shop up in Salida, CO.
https://goo.gl/maps/JVMpcXDMAAF2 If you have an SUV with clearance and 4x4 try the drive over Tin Cup pass starting at St. Elmo ghost town.
https://www.flickr.com/photos/vincentjohnson/14835844425/in/album-72157603346855148/https://www.youtube.com/watch?v=PmGKODUBp7chttps://goo.gl/maps/q7NmNwNfx6C2Gunnison has a old school steakhouse called Ol Miner's, try them, then try the brewery right next store.
https://goo.gl/maps/efAF8maq3xM2I had good luck staying at the ABC Motel there.
https://goo.gl/maps/HU2AgBbn9BQ2When you get to Montrose, CO. if you have time, take 550 south to at least Ouray, or Silverton. You also aren't going to be that far from Masa Verde & the Four Corners at the point. Might be worth the detour and then head back north on 191.
Sadly I know little about route 50 in my own state of Illinois.
Good luck on your travels.
Cheers,
Vincent