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The land under today's townhomes was once part of the vast holdings of the Lee family of Virginia. In his 1802 will, George Lee — heir of Thomas Ludwell Lee II — named his plantation "Farmwell," and for most of the 1800s that's what this place was called: Farmwell, and later Farmwell Station once the trains came. A post office operated at the crossroads of Ox Road and Church Road as early as 1800. This was rural, agrarian Loudoun — Quaker farmers, dairy herds, and rolling fields.

In 1841, John Janney — a Quaker lawyer who, at the 1840 Whig convention, lost the vice-presidential nomination to John Tyler by a single vote — acquired part of the Lee-family land that became Ashburn Farm. Since Tyler became president when William Henry Harrison died a month into office, Janney missed the presidency by about as narrow a margin as American history allows. Later, he presided over Virginia's 1861 Secession Convention, where he personally opposed secession.

His farm gave Ashburn its name — though how is the town's oldest argument. The beloved legend says lightning struck a giant ash tree on the property, and it burned and smoldered for days while crowds came to watch. Historian Eugene Scheel offers a quieter reading: "ash" for the groves of ash trees, "burn" from the Old English word for a small stream. Either way, the first recorded "Ashburn" appears around 1870, and the village officially took the name in 1896.

The rail line that became the Washington & Old Dominion defined Ashburn for a hundred years. Confederate forces tore up the tracks during the Civil War; the rebuilt line afterward made Ashburn a shipping point for dairy bound for Washington. The village that grew around the station — the stretch of Ashburn Road still standing today, now a designated historic district — was a classic Virginia railroad hamlet: a general store, a mill, churches, and farmhouses built by local craftsmen. When the last W&OD train ran in 1968, the corridor became the trail at the center of community life today.

For decades after the trains stopped, Ashburn stayed a quiet crossroads ringed by dairy farms. Loudoun approved Ashburn Village in 1985, and it opened in 1988 — 5,000+ homes on 1,500 acres — followed by Ashburn Farm, Broadlands, Belmont, and eventually Brambleton. The Dulles Greenway opened in 1995 and tied it all to the airport and the Toll Road. In 1992 the Redskins moved their training facility here. A community of a few hundred in 1980 passed 46,000 by 2020, with some of Virginia's top-rated schools and the nation's highest county median income.

Ashburn's second transformation was nearly invisible until the buildings grew too big to ignore. Thanks to early-internet fiber, cheap land, AOL's presence, and proximity to Washington, data centers began clustering here in the 1990s and accelerated sharply after 2013. As of 2026, Loudoun hosts one of the world's largest concentrations of data centers — on the order of 200 operating campuses with dozens more approved or in development, though published counts vary with how a "data center" is defined — and a significant share of global internet traffic passes through Northern Virginia's "Data Center Alley". The industry pays a remarkable share of the county's taxes — and drives its loudest debates over power lines, land use, and what Ashburn should become next.

The Silver Line's Ashburn Metro station opened in November 2022, making this the end of the line — or the beginning, depending on your direction. One Loudoun has become the de facto downtown. A town named for a burning tree (or maybe just a creek) now anchors one of the world's largest concentrations of data centers — while still running youth basketball leagues, packing the trail on Saturday mornings, and arguing about school boundaries like any other town.