15 Church is a great bet, my wife and I just ate there a couple of weeks ago and had a really great night. We chose to eat out on the covered patio (get a reservation). The outdoor "Patio menu" which is a bit more relaxed than what's offered inside. We each had a couple of cocktails, an app and fantastic meals for under $100 which I think is acceptable for the quality of what's offered.
With a handful of sales guys there will be plenty to look at as well.
A Wednesday should be no issue getting out of the track. If you wanted to walk someplace when track lets out you could always hit the Brook Tavern which has great food just no (or very limited) outdoor seating.
Wishing Well is great but it's out of town and it's more like a place I would take my mom.
Uber is only starting up this week, so it's hard to say how it will work at the track this year. I'm guessing there will be plenty of Uber but they will have a hard time figuring out all the congestion around the track. If you have the budget, get a limo for the day. And bring a couple of tiny guys and dress them up in nice suits. People will think they are jockeys, which are babe magnets in Toga.