I love love love Wayside. Charlottesville is a tough food town. People are very proud of local choices but there are sadly few to recommend. Another place to try is Michie Tavern. It is a tourist haunt but you can get your chicken-and-country-ham fix all at once. There is a market called Feast on West Main Street that has some gourmet shops and eateries in it. It’s purple and hard to miss.
Foods of All Nations is a lovely place to spend some time gawking at all the neat stuff and it’s much less pretentious than Whole Foods.
If you stumble into lovely Orange, VA where James Madison’s Montpelier is located, head downtown for Elmwood at Sparks. They’re not open on Sundays but worth dashing to on a Saturday just to see what’s being whipped up. Orange is also a beguiling, dog-eared kind of place, the sad Southern town.
More favorites include The Local in Charlottesville’s Belmont neighborhood, Revolutionary Soup on the Downtown Mall and Siips for cheap lunch and a glass of good local wine, also on the mall.