A potential Stars Hollow can't be judged by adorableness alone.
These people are serious about their history. A group of concerned citizens banded together in the early '90s to save this city from being bulldozed in favor of a major highway and a potential mining operation, and thank god they did. Instead, this Shenandoah Valley hub has pretty much anything you'd be interested in. Art? Numerous galleries. Theater? They're home to the Blackfriar's Playhouse, the only re-creation of Shakespeare’s indoor theater. There are also the requisite number of antique stores (which I've managed to avoid...cute town tends to equal pricey vintage) and plenty of history, including but not limited to the Woodrow Wilson Presidential Library and the Frontier Culture Museum.
There is also plenty of the good stuff - coffee, restaurants, nature (lots of good people in local government making good things happen for the rivers and trees). Staunton has all the small, local stores covered, including stores for clocks, party, books, music, cameras, hobby, and many more.
Guys, this may be the closest Stars Hollow hit I've come across! They even have an ongoing campaign to save a local bridge. Flabbergasted.
*Honestly, I couldn't resist. It's the first thing that came to mind, and I have been promising to keep it real. ;-)