Personally, unless you prefer seats, I wouldn't bother with reserved seating. It's easy to work your way into a good spot on the rail and the action and vibe is much better there. When I sat in the grandstands, it felt too far from the track and there wasn't much buzz. We got into a rhythm of going to paddock, placing bets, getting a beer, going to rail, rinse, repeat. Even on Bluegrass day, the crowd wasn't too bad and that's probably way more than the fall meet.
You can bring in a tailgate chair and set it up in the rail area if you aren't able to secure a bench to sit on. Or have your crew all bring bag chairs and just set them up in a circle where you want to be near the rail. And you can always head to one of the bars under the grandstands and sit down for a bit if you need to. Plenty of betting windows in there as well.
So save the $60 bucks per person and use it to bet!
As for parking, get there a little early and park up close in the paid lots. It's $5! And you have about a 100yd walk to the front gate. I think we entered via Gate 2 and were probably two hours before the first post? Spots were super easy to come by, $5, and again, this was the Bluegrass.
Our first year, we did the Phoenix Room and got dressed up and paid the $40 a person for the fancy buffet. It was nice. Food was delicious, but I could have taken it or left it. Keeneland standard concessions are fantastic and not unreasonably priced. Corned Beef Sandwiches are the bomb! I didn't feel like the sit down meal was worth it. And I definitely wouldn't do it if it was away from the track.
Some cool local places to eat, drink after the race:
Country Boy Brewing - They just made the Keeneland Sale Ale! Cool little microbrewery in town.
Saul Good - Fantastic selection of awesome pizzas and pub grub. Really good.
Tons of good little divey bars in that general area around Short St. And the awesome thing is they've got TVG playing on all the TVs!
Love Keeneland! Have fun!
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