September - November
Charlottesville isn’t the kind of traveler’s mecca that makes it impossible to get a hotel room or a restaurant reservation any time of year, but the return of the UVA students always causes the city to swell a bit. Even though the Cavalier football team can’t play their way out of a paper bag these days, faithful fans still fill Scott Stadium and most of the nearby hotels every home game weekend. Leaf peepers flock to the Shenandoah Valley every October, and special events like Family Weekend at UVA in November and the September Foxfield steeplechase races always bring crowds, but Charlottesville is never Disney-World-or-Labor-Day-weekend crowded. Traffic is always a nightmare around UVA whenever there’s a football game or a big event at the John Paul Jones Arena, so if you’re not attending, those might be good days to head for the mountains out of town and go hiking. The weather couldn’t be better for outdoor activities this time of year.
December - April
The winter isn’t usually very harsh here (2009-2010 was an aberration with its many feet of snow), so there’s no real reason to stay away. In fact, you might find the best deals on hotels during this time of year when the tourists aren’t really around. Monticello is lovely when decorated for the holidays, and there’s even some decent skiing at nearby Wintergreen Resort or Massanutten Resort. It’s no Breckenridge, but the crowds aren’t too bad, except on holidays.
May - August
Charlottesville definitely has a quieter feel to it when the students are gone. Summer is a great time to bring your family for an educational trip to see all the presidents’ homes, and the gardens at Monticello are spectacular when they’re in full bloom, but the heat and humidity are a major detraction in the summertime. Locals like to beat the heat by going tubing on the James River, or taking a dip in the chilly Blue Hole at Sugar Hollow.