I'm a W&L undergrad, so I wandered into this thread out of curiosity and thought I'd share thoughts on the town since I am procrastinating right now:
Food: Pretty good for a town of less than 10,000. But then again, it's a town of 10,000. There are all your typical fast food restaurants as well as a couple of sit-down chains--though no Chipotle/Qdoba or Chick-Fil-A, unfortunately. There are lots of nice little lunch places in town--Blue Sky and Joyful Spirit are probably the best, although guys won't feel very manly eating there. Sweet Treats is also nice, McCoy's and Macado's have decent sandwiches. For something a bit nicer, there are a handful of options. The Southern Inn is overrated (except for a great brunch), Tuscany is eh, The Sheridan Livery is almost always pretty good, and the Main Street Bistro is my favorite. It also has the best lunch in town: you won't pay much more than you would for a quick sandwich, and the quality is excellent. The Red Hen has overpriced local farm/livestock food, and there are a couple of other niche restaurants. Other than that, there are perplexingly many pizza/pasta/sub places (Salerno's is my favorite). The Healthy Foods Co-Op also has a mostly vegan lunch cafe (easily missed) that is surprisingly filling and usually quite tasty. If you can figure out their weird opening hours, don't forget to check out the Pink Hut for ice cream and Kenny Burger for unadulterated grease. Don Tequila's has pretty bad Mexican food, but if you're craving enchiladas, go for it and get a Jumbo Texas Margarita or two to top it off.
Campus: Gorgeous. The law school isn't as impressive as the Colonnade (national historic landmark), but the two campuses are separated by well less than a mile. Absolutely stunning, can't say enough about it really. Have only been in parts of the law school; it seems fairly nice. Very quiet, in my experience. Pretty good gym facilities for such a small school.
Town in general: Great feel and very pretty--IF you like small towns. Pretty much dominated by W&L and VMI. Cutesy shopping; the town plays up its historic nature (probably a bit too much--nothing much actually happened here).
Stuff to do: You've probably heard this before. Only Macado's and The Palms (which sucks) really feel like bars, although I think law students may hang out at a few of the restaurant bars as well. We have one three-screen movie theater and practically everything else is at least 45 minutes to an hour away (bowling, ice-skating, big shopping, concert venues, etc.). The school does a nice job of bringing speakers and stuff in, but don't fool yourself--the town is small and isolated. The undergrad scene is dominantly Greek, so I don't have too much to offer you in the way of creativity, but friends at the law school tell me that social life is very tight, because of the class size, and involves lots of house/apartment parties and law school functions. IM sports are pretty big, especially football and softball. So the town isn't much, as you've probably heard, but the surrounding country is just as beautiful as people say. If you are outdoorsy, you will love it--cool stuff like Natural Bridge and several caverns close-by, lots of hiking/cycling to do, and oddities like Safari Park and Foamhenge (exactly what it sounds like). A lot of wineries near Charlottesville, which is just an hour away and a nice change of pace.
Miscellaneous: The Honor System is absolutely incredible (without peer, from everything I've been able to gather) and there is a genuine community here, even among law students, that you don't find many places. Hope this helps!