Chester Street — “Why did they put a diagonal street in the middle of Front Royal?” 

Have you ever turned onto Chester Street, that diagonal road that runs from Main Street up to Royal Avenue, and wondered what town planners were thinking?

Did you know Front Royal was built around Chester Street, and not the other way?

You have heard of the Silk Road of antiquity… that all roads lead to Rome… or in and out of the Shire or Mordor if you are a Hobbit fan.

For a long time in the early days of Warren County there was one road that led in and out of town.

That road was Chester Street, which was the original road running up to Chester Gap to the south, linking the Valley community to vital markets over the Blue Ridge, and on the other end meeting up with the Shenandoah for river-borne trade items. Chester Street was named for Thomas Chester, who operated a ferry across the Shenandoah in the early 1700s. Think about that next time you’re stuck in traffic on the bridges…

When you go up Chester Street, you are following in the footsteps of Front Royal’s earliest citizens!

Of course, people also traveled into town via Chester Street from surrounding dry counties to have a drink — and maybe gave rise to Front Royal’s nickname of Hell Town. But that’s another story for another day (the road to Helltown?).

Chester Street was home to leading families of the area, and still boasts at least seventeen historic buildings dating back to the 1700 and 1800s.

During the Civil War, the rebel spy Belle Boyd stayed at a cottage behind Main Street (later relocated to Chester Street). And during the Battle of Front Royal, Stonewall Jackson rode his horse on the same road we now walk or motor down.  Nowadays you just have to watch for traffic. But we hope you enjoyed this stroll down memory lane.

Stop by the Warren Heritage Society for an in-person experience with local history. We have buildings, artifacts, and history buffs to discover.