These guys are on a football road trip. They're not hitting up Middlefork or Jean Farris.
On and around Campus:
Pazzo's - Pizza and beers
Local Taco
Tin Roof - Student bar
Tolly Ho - Late night staple
Two Keys - Student Bar
If you're looking for a slight older crowd downtown is a short walk from campus, 4-5 blocks down the hill. Uber is also very prevalent.
Belle's Mixed crowd, cool rooftop, wide variety of bourbon
Parlay Social - Older crowd
Harvey's
Rosebud
McCarthy's
Goodfellas Pizza - Best pizza in town and open late
Pies & Pint - Also good pizza and really good beer list.
Tony's - doubt you all want it but best steakhouse in town $$$$
For recharge breakfast go to Winchell's. Grab a spot at the bar. It's amazing.
Also, Lexington has a great brewery scene. All these are really good and in or around downtown. They should all have solid crowds, music and food trucks each night.
Blue Stallion - My fav, German style beers
Country Boy - Cool little place with good mix of crowd
West 6th - Good beer, big, and has a goot restaurant on site.
Mirror Twin
Ethereal
Keeneland is a must. If you have time the Bourbon Distillery Tours are a ton of fun. The two best close to Lex are Buffalo Trace or Woodford Reserve.
*I bolded the things I would personally suggest.