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Harrisonburg is a good 60 miles from Winchester. So if you would be up for an hour commute. That being said though,there wouldnt be the kind of rush hour traffic youd get if you lived in suburban Washington, D.C.
Both towns are equally nice- . You could compromise and live somewhere in between Harrisonburg and Winchester- perhaps New Market or Woodstock.
Winchester is the oldest town in the valley and has the Patsy Cline legacy.
Harrisonburg is a nice college town, and has a bit more to do than Winchester in terms of night live, etc.
The Shenandoah Valley is pretty conservative, but I dont think youd run into any major problems . Richmond and D.C. tend to have more gay people I think.
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