The Only Diagonal Street in Old Town Alexandria—and the History Behind It

Alexandria, VA – At first glance, it looks like just another charming Old Town street—lined with brick, framed by blazing fall color. But look a little closer, and you’ll spot something unusual. Commerce Street is the only diagonal street in the original grid of Old Town Alexandria.

Once you notice it, you can’t unsee it. And its odd angle isn’t an accident.

Commerce Street first appeared on a 1798 map drawn by George Gilpin, at a time when Alexandria was one of the busiest ports on the Eastern Seaboard. The city’s prosperity depended on what surrounded it—particularly the farms of Fairfax County, which originally produced tobacco before switching to wheat and other grains as soil exhaustion set in during the 1790s.

That shift raised a practical question: how did all that agricultural bounty get to market?

The answer rolled in on massive Conestoga wagons, carrying grain and tobacco along Little River Turnpike, one of the earliest toll roads in the country. The route ran from Aldie in Loudoun County, through Fairfax County, and into Alexandria, where it became Duke Street.

Today, Commerce Street is cut off from Duke Street in the 1400 block. But originally, it ran diagonally for two full blocks—straight through to King Street.

That diagonal mattered.

Instead of forcing heavily loaded wagons to grind through sharp 90-degree turns—common in a rigid street grid—Commerce Street offered a gradual curve. The design made it far easier for those enormous wagons to navigate toward the wharves at the foot of King Street, where goods were transferred onto ships bound for Europe.

In the most literal sense, Commerce Street kept Alexandria’s economy moving. Its unusual angle is a quiet reminder that Old Town’s layout wasn’t just about symmetry or beauty—it was shaped by commerce, engineering, and the daily realities of an 18th-century port city.

So the next time you walk Commerce Street, remember: that gentle diagonal once helped turn wheat and tobacco into global trade.