October could be the best time to visit the Commonwealth of Virginia; the peaking fall foliage draws plenty of leaf-peepers, and Virginia Wine Month means festivities and celebrations galore. From concerts to barrel tastings, hay-rides to artist displays, the month will be jam-packed with fun events. It all kicks off at Monticello (how fitting!) when The Governor's Cup for White Wines will be presented to one lucky Virginia winery as the opening event for October Virginia Wine Month. Looking to stay in the area? Check into Keswick Hall, the gorgeous 600-acre estate managed by Orient-Express, and you might just find yourself joining in the grape harvest (or stomping the resort's own grapes!) Plus, Keswick hosts a wine tasting every Thursday in Fossett's Bar with Keswick's Richard Hewitt, one of the few Master Sommeliers in Virginia.