The NY Times did just 36 hours in Richmond:
http://www.nytimes.com/interactive/2016/09/17/travel/what-to-do-36-hours-in-richmond-virginia.html?_r=0
It is my hometown and my family still lives there. Here are my recommendations (just my opinion):
1). Maymont House (do you mean the Dooley Mansion)? No that isn't a must do. If the weather is nice sure Maymont is fun, but if you don't have kids with you I can think of tons of other things to do.
2). VMFA (Virginia museum of fine art) is excellent, to me that is a must do. And the Virginia Historical Society museum is practically next door, I would go there as well.
3). No, there aren't wineries around, you need to head west via 64 towards Charlottesville for that. BUT RVA is a microbrew town, so there are many breweries to visit if that's your fancy.
4). The food scene is EXCELLENT. Call and make a reservation NOW for Saturday night
5). Get drinks at the rooftop bar at Quirk
6). Visit one of the islands on the James
7). Go to Churchill, take a tour of St. John's church
8). Visit carytown
9). Have fun