bethl5

Neither my best friend or I have ever been to Virginia, so we'd like to spend a long weekend there in late October or early November. What would be a good area to visit that offers unique, "boutique"-style shopping (more "downtown" rather than big shopping malls or outlets), good restaurants and things to do? Thanks!

Hobbert

Winchester, Leesburg, and Charlottesville all have near downtown areas with shopping and restaurants. Leesburg also has a decent outlet mall if that's of any interest.

bankbabe

Charlottesville or Williamsburg

schlegal1

Exactly what Hobbert said. You also might consider Culpeper, though it is quite small.

Charlottesville is probably going to fit the bill as it has great shops, restaurants, and also has tourism activities like historical sites at Monticello, UVA, Ash Lawn (though I think it is now called Ash Lawn Highland), outdoor activities in close proximity, plus wineries/distilleries/breweries nearby to tour and taste.

SusieQQ

Staunton has a lot to offer including a historic hotel, a theater, a church with lots of Tiffany windows, historic buildings and shopping. Take a look.

starrs

Check out this place - The Inn at Meander Plantation
http://www.meander.net/

schlegal1

I live close to Staunton and consider it "my" town. I am embarrassed I didn't think of it. On the other hand there is not a lot of boutique shopping. There is one nice shopping street and not much else. There are other activities as well. Depends on what priority the shopping part takes.

Starrs, that place looks nice but really secluded. It isn't close to anything --have you stayed there?

obxgirl

Old Town Alexandria would be my choice. Many good suggestions here.

Birdie

I'd also take a look at Middleburg but it's been a few years since I've been there. Do you mind if I ask you your age and what types of boutiques you're looking for?

sf7307

Middleburg is historic and charming. We stayed at the resort hotel - Salamander Resort & Spa - and loved it. Very comfortably furnished, beautiful common areas, walking distance (10 minutes) to town. The restaurants in the hotel are excellent.