Lucky you, ZDAV ! In spite of being a KY native, I've only done the Derby once, 5 years ago. The one thing we had not known ahead of time---and it could have cost us----is that you need to show proof of your SS# in order to collect. (not sure if there's a minumum $ amount for this requirement, but it is probably at whatever point they start to withhold taxes). Hubby hit a race for $960, so we were excited. Turned out neither of us had any SS# doc on us, just the usual DL, CCs. Finally, he remembered that he carries a wallet-size copy of his DD-214 (from US Army, decides ago), which does show the SS#. (Glad we didn't have to find out what would have happened otherwise)

Your experience (RV, lots of friends in the group) will make it memorable---even if it's not YOUR bachelor party ! As much as I enjoyed the races----all the color, sounds, hats both elegant and crazy----the highlight for me was seeing Walter Cronkite and his wife passing 2 feet in front of me in a golf cart !
At the track, I highly recommend 2 things (both alcohol-related, as it turns out):
a Bloody Mary at the Finlandia booth, and a Mint Julep, preferably from the vendor roving in the stands. I was amazed at how icy, minty and fresh it was...and on a hot day in May, there's nothing better. I suspect it would still be a good choice on a cool, rainy day in May.

For dining out, these were our memorable experiences:
Del Frisco's - delfriscoslouisville.com and
Napa River Grill -napariverlouisville.com. Not sure about convenience for your Fairgrounds location, but both were ideal for us from our hotel in Jeffersontown.You might still be able to get reservations, and you will need them, for any non-family dining or non-fastfood place that you decide to try.

I'm sure you'll get good advice for other great places. Sorry I can't offer suggestions on clubs, bars., etc---but I suspect you'd prefer that advice to come from someone UNDER 60 ;-P

Enjoy yourselves, be safe, and be sure to bet a few longshots !

It's actually more fun to go to the Oaks on Friday. + it will easier to get tickets/seats.www.kentuckyoaks.com

Are you doing the infield or do you have grandstand tickets?

By the way, if you are doing the infield this year, you can take a cooler this year. This has not been allowed for the past few years. You can take lawn chairs too, but have to use a designated gate.
You can catch a bus from the Fairgrounds to Churchill Downs-hope it works well as it is a private company this year who sued to keep TARC (who has done a great job year after year) from transporting people to the tracks. The private buses will not be as numerous or as nice as the TARC buses.

Have a wonderful time.

Yes, coolers allowed this year, but you must use certain gates and no booze/glass allowed. Coolers will be searched.