I'll have to vote for Charlottesville, VA as well. I grew up there. If you have time to spare this is one of those cities you can just walk around and get lost in the history. It's big enough that you won't run out of stuff to do but small enough you won't feel like you're a grain of sand at the beach.
The original Main Street has been bricked over and turned into a pedestrian mall, known as the Downtown Mall- they've since planted trees in the middle and it's just well, quaint. All the old buildings along main street from the early 1900s still line the street yet new businesses and restaurants occupy them. At the West end their is a concert pavilion and every Friday they have "Friday's After Five" where after 5pm a huge turn out of the population comes out for a free concert. Usually they have a beer truck or two also
Charlottesville is unique in the fact that probably more than 75% of the businesses there are "mom and pop" shops, not chains, and if they are a chain it's locally owned, not by a mega corporation. You'll still find chipotle and mcdonalds but the majority of places are individually owned and operated and everyone who lives there understands that you need to support local business in order to keep the local economy flowing. It's been rated as one of the best places to start your own business and succeed.
At the East end of the Downtown Mall is my favorite restaurant "Es Cafe" serving awesome original dishes and a full bar. You can stay at the Omni hotel which is adjacent to the Downtown Mall which is pretty neat, across from this is a indoor ice skating rink too.
The Boars Head Inn is also a nice place to stay and they used to do a lot of Hot Air Balloon launching from there as well... Def something worth doing so you can take in the scenery and see how Charlottesville is nestled in between the Blue Ridge Mountains and the Appalachians.
You'll of course want to do some history sight seeing as well, you're in the prime spot if you're there - Monticello, Thomas Jefferson's home (back of every Nickle) is down the street as is Ash Lawn, home of James Monroe. And, of course you can't go up there without stopping in for a bite n drink at Michie's Tavern; an 18th Century Inn.
If you're a wine person you can of course check out the abundance of vineyards in the area as well, Virginia actually boasts a large number of well know vineyards.
Charlottesville even has it's own Observatory! McCormick Observatory.
If you're an art person you may want to check out the McGuffy Art Gallery as well. If you like races, you might want to conincide your trip with the Fox Field Races, its a spectacle in itself.
As for resturants and bars there's so many, but I think my top favorite ones would be
Es Cafe
La Cocina del Sol
C & O Restaurant (upscale)They make the Best Greyhound Drink, fresh squeezed juice for a mixer!
The White Spot (Good greasy Cheese Burger sometimes cooked by Elvis, the one that didn't leave the building)
Tokyo Rose if you like Sushi
Revolutionary Soup for the best of fresh made soup daily n more.
If you're feeling mexican check out Guadalajara.
and what Charlottesville adventure is complete without a trip to the FAMOUS
Bodo's where the bagels are always warm and fresh when you order.
You'll also want to check out St Maarten, ZoCaLo, Star Hill, Orbit Billyards and South Street Brewery as some of the great watering holes.
Omni Hotel
Boars Head Inn
Monticello
Ash Lawn
Michie Tavern
McCormick Observatory
Fox Field Races
Virginia Wine
The orginal
C & O Station still stands but has been turned into a business center still kind of neat to see, and it's at the end of the Downtown Mall.
That should keep ya busy for a bit, hope this helps!