I live in Lexington GE, so holler at me if you need anything.
Rupp Arena is in a civic center. The center is open but the arena won't be unless a game is going on. We just redid the entire building so at least driving by it and checking it out from both the High Street and Main Street side by Triangle Park is at least worth your time.
Right across the street from Rupp is Tony's (link:
https://tonysoflexington.com/gift-c...eTjkvpmhrIyyp4q_Eu2wpxPDepB-PCnoaArgJEALw_wcB) and down Vine Street is Jeff Ruby's ( link
https://www.jeffruby.com/lexington?...foYYUOh9ERQkserCyyqpzpXDlSjbtlk0aApBgEALw_wcB ) Both are excellent high end steakhouses so be prepared to spend some coin, but you and your lady will love them. Malone's mentioned above is also an excellent choice. Just wanted to offer two options that are downtown close to Rupp.
I'm not sure about horse farm tours. I live here so it's not something I ever do. Usually you have to make reservations in advance. A quick Google search showed me we actually have Horse Farm Tour agencies here...I honestly didn't know that. Id check with one of them.
I'd recommend the Woodford Reserve tour because the drive out there from Lexington takes you through scenic horse farm country. Just gorgeous especially in the fall. Also, the Town Branch distillery is downtown here in Lexington basically across from Rupp Arena. I've not done that tour as I'm not a fan of their bourbon.
I'd recommend (haha yet again something very close to Rupp Arena) Justin's House of Bourbon if you want to find some quality bourbon and rare stuff. They've got all manner of good bourbons for sale in there.
I think that covers all your questions. RailBird has been growing in popularity. I know last year or the year before they had a hell of a time with parking and traffic. I may pick up some tickets myself just haven't decided yet. It's always a blast and yall will have fun.
If you have any more Lexington questions just holler at me.