In 1890, the United States Congress passed legislation improving Military Road and turning it into a wide boulevard for traffic.

[6] Arlington County officials refused to challenge the proposal, claiming this was a fight only for the federal government (owners of the road).

In 1909, the federal government began posting military guards along the road to ensure that speed limits were obeyed.

[9] Later that year, the federal government won an eminent domain case against landowners who owned property to the east of Military Road, allowing the street to be expanded by 20 feet (6 m).

With the construction of Wilson Boulevard and Chain Bridge, major impediments to traffic occurred on the Virginia side of the Potomac River as older streets curved around natural landscape features.

Hoover Field's single runway was crossed by Military Road,[14][15] and an airport employee had to stop traffic with a rope when planes landed.

In August 1931, Arlington County and the U.S. Army agreed to end a dispute over who should continue to maintain the road, with the county taking responsibility for the road itself and the military assuming authority over connections and on/off ramps to nearby military facilities like Fort Myer and Arlington National Cemetery.