Historic downtown Leesburg is a walkable 18th-century core along King Street and Market Street — boutiques, restaurants, breweries, and the Wentworth Center for the Arts in the historic theater. The Leesburg Flower & Garden Festival (April) and the Leesburg Christmas Parade (December) close downtown for street events.
Loudoun County wine country is the marquee draw — 40+ wineries within 30 minutes of downtown Leesburg, from Chrysalis and Stone Tower to Sunset Hills and Bluemont Vineyard on the Blue Ridge. Weekend tastings run year-round and the Loudoun Wine Fest (August) is the summer highlight.
Morven Park is a 1,000-acre estate with a Greek Revival mansion, a Museum of Hounds and Hunting, formal gardens and the Morven Park International Horse Trials (October). Oatlands Historic House and Gardens (south of Leesburg on US-15) is a National Historic Landmark with a formal terraced garden. Ball's Bluff Battlefield Regional Park preserves an 1861 Civil War battlefield on the Potomac bluffs.
Leesburg Corner Premium Outlets offer 110+ outlet stores at US-15 and Fort Evans Road, and the Journey Through Hallowed Ground scenic byway follows US-15 from Leesburg south through 175 miles of Civil War history and farmland.
There is more within easy reach: Loudoun wine country (40+ wineries within 30 min); Morven Park estate and horse trials; Oatlands Historic House and Gardens; Ball's Bluff Battlefield on the Potomac; Leesburg Corner Premium Outlets. Seasonal highlights: spring Flower & Garden Festival and Morven Bloom, summer wine harvest and pool season, fall Loudoun wine-harvest weekends and Morven Horse Trials, winter cozy downtown pubs and holiday parade.