4 Best Sights in Middleburg, Northern Virginia

Two miles east of Middleburg is the Chrysalis Vineyard, a 412-acre-and-growing vineyard dedicated to producing both old- and new-world varieties of wine and hoping to revive interest in the fabled Norton, a grape native to Virginia. The owner maintains she'd rather grow the world's best Norton than the 400th best cabernet. Wine tastings here emphasize the educational experience, as volunteers present each wine in detail to tasters. The entire experience takes about 45 minutes. Afterward, buy a bottle of wine and snag a picnic table near the tasting tents. Grills are available on a first-come, first-served basis. Chrysalis is also host to a number of music festivals throughout the year, including a jazz festival in May and the Norton Wine & Bluegrass Festival the first weekend in October.

Five miles south of Leesburg on Route 15, Oatlands is a former 3,408-acre plantation built by a great-grandson of Robert "King" Carter, one of the wealthiest pre-Revolution planters in Virginia. The Greek Revival manor house was begun in 1804 in the Federal style; a stately portico and half-octagonal stair wings were added in the 1820s. The house, a National Trust Historic Site, has been meticulously restored, and the manicured fields remain host to equestrian events from spring to fall. Among these is the Loudoun Hunt Point-to-Point in April, a race that brings out the entire community for tailgates and picnics. The terraced gardens here house boxwoods, roses, a reflecting pool, and the Carter tomb. Guided tours of the home and grounds are available daily.

The "Virginia Winery Guide" lists each of the state's wineries (many offer tours and tastings). It's free and can be picked up at visitor information centers throughout the state or by on the Virginia Wine Board's website. From there you can also find descriptions of more than 500 wine events and festivals that take place each year.