Another from Richmond- thought I'm a transplant, and I've only been here for 14 years. I think a lot depends on what you are into- shopping, history, the party scene, music?
Maymont park is a great place, which, while a little colder right now, is beautiful. Especially check out the Japanese gardens there. For shopping, definitely Stony Point(my favorite- has a Saks with a Chanel and
Gucci boutique, and a stand alone LV next to Saks) and Short Pump Town Center (my second favorite store is there-
Nordstrom!).
I'm not so big on Shockoe Bottom and Slip- if you are into the party scene, they are great. However, Bottoms Up Pizza in the Bottom is a yummy, Richmond-only thing to do. I'm more particular to the Fan area and the restaurants there (Carytown is a GREAT place for shopping AND eating). Strawberry Street Cafe is one of "the" landmark restaurants there that a lot of people consider a must see.
If you're looking for something relaxing, Nesbit Salon in the Fan on Main Street is one of the best known salons in the area. It can be a little pricey, however, and is a bit on the snooty side (I got my hair done there for YEARS, and they are STILL uppity with me after the thousands I've spent there).
The Jefferson is a great place, and even if you don't stay there, just stop in for drinks. It's worth it just to sip coffee or cocktails in the lobby lounge.
If you haven't been to Williamsburg before, and have time, definitely take a quick side trip down there. Merchant's Square has some great shopping and dining (as in The Trellis, home of Death by Chocolate) and is at one end of the main part of Colonial Williamsburg. It's also a lot of fun to eat at the taverns (King's Arms is by far the best, though you need to make reservations if you want to have any chance of eating dinner there).
Umm..if I think of anything else I'll post that too