McIntire is one of the best parks in the state. Huge park with street and bowls.
Skate shops come and go, but there is a new shop there now (haven’t been). When I lived around there people got their boards from the ski shop. HOWEVER, about 40 minutes away in the small town of Louisa, there’s a shop called Strange House that is pretty rad. He carries a lot of old school/reissue type stuff but it’s worth going just to see his inventory. It’s about halfway between Charlottesville and Richmond. Make sure he’s open before going, hours are weird.
www.strange-house.netIt’s a college town so there’s bars. Food is mostly chain stuff, but Mellow Mushroom has great pizza and a killer beer selection.
Charlottesville’s main attractions are the architecture, wine country, and breweries. You have to go a ways out of town for the good breweries and wineries. Blue Mountain brewery is a cool spot, but is still a 30-40 minute drive from downtown. In town there’s South Street and Champion brewery which are good enough.