Winchester, Virginia is one of those places that is easy to miss when you visit the this part of the world, but that would be a serious omission. Granted that judging from the many “For Sale or Lease” signs in town you could be forgiven for thinking that this is a place where more people are headed out than headed in, but economic hardships aside, Winchester is a pleasure to visit at any time of the year. One of the unique features of this Rout 81 town is Loudoun Street, the downtown pedestrian walkway lined with restaurants, great architecture, and a surprisingly active art scene. One rather interesting gallery is the small, but quaint Sleepy House Studio, which showcases a rather eclectic number of art pieces and where the resident artist can be found outside working on the next art piece (see photo above) while enjoying a warm spring day. And if it is history that you have in mind, then you should head on down to 32 West Cork Street to visit the George Washington Office Museum where the General himself spent about 15 months while supervising the construction of Fort Loudoun. However, hanging around the pedestrian Loudoun Street will be good enough for most photographers. From young jugglers practicing their skills to musicians trying to get some rent money, it seemed that this is the sort of town where the arts don’t stay inside when the sun is shining.
What remains a challenge is getting to the place. If you drive there from the Washington, DC area, plan for a good hour-and-a-half to two hours worth of driving west on Interstate 66 and north on Interstate 81, depending on traffic. Alternatively, you can get there via the old Route 50 that crosses the horse-crazy communities of Middleburg and Upperville, and where some of the area’s best restaurants can be found, not to mention a slew of new wineries trying to transform the Virginia countryside (and Route 50) into the next big thing for wine lovers. So while it may take some patience to drive to Winchester, you will be amply rewarded by scenic countryside, a photo-friendly community with a flourishing art scene, and a handful of wineries that are eager to show you what they have been up to lately. Not a bad to spend a day on a weekend.