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The absolute big one for Winchester is the Shenandoah Apple Blossom Festival, or locally known as The Bloom. It happens every year the first weekend in May, and draws about 250,000 (yes, a quarter-million!) people here - it's a huge festival, with two big parades. The first is the Fireman's Parade, on Friday night, and has over 300 firetrucks on parade -- it's the single largest display of fire-fighting equipment at one time in the USA. Kind of fun! Then Saturday features a big midway downtown, with lots of food and fair-type happenings all over town, followed by the afternoon parade. Check out their web site: www.thebloom.com , has all the info.
Second for big events are the Civil War re-enactments. Each October, the Battle of Cedar Creek is re-enacted, with all the fun that surround those. This July, 2006, an additional re-enactment is taking place here: the Battle of Manassas. Now before you ask, Yes, they moved the re-enactment from Manassas to here in Winchester... confederate soldiers are rolling over in their graves! But should be fun.
Go to the Winchester-Frederick County Convention & Visitors Bureau website: www.visitwinchesterva.com for all the details and more.