Upper South

States: Virginia

Start near: Washington, DC (starts here)

Bull Run to the Bloody Angle

The Northern Virginia Civil War loop

Bull Run to the Bloody Angle is a ~240-mile back-roads route, a loop from Alexandria, on US 29, US 50, US 15, VA 3 and US 1, driven in 2–3 days, that stays off I-95 / I-66 through the Upper South.

Open the interactive map →

Drive

Loop from Alexandria

Distance

~240 miles

Time

2–3 days

Highways

US 29 · US 50 · US 15 · VA 3 · US 1

Avoids

I-95 / I-66

Region

Upper South

More Civil War per square mile than anywhere on Earth: both Bull Runs, Mosby's partisan country along the John Mosby Highway, the biggest cavalry battle ever fought in North America, and the terrible quadrilateral — Fredericksburg, Chancellorsville, Wilderness, Spotsylvania — where 100,000 men fell within fifteen miles. Driveable from DC, unforgettable in any direction.

📍 Virginia Civil War Trails' red-bugle signs mark practically every crossroads on this loop.

The drive, segment by segment

Bull Run & Mosby's Confederacy

Alexandria → Warrenton · ~75 mi

Manassas's twin battlefields, then US 50 — the John Mosby Highway — through Aldie, Middleburg and Upperville, where the Gray Ghost's partisans owned the night.

• ⚔️Manassas: Henry Hill — Manassas

  July 21, 1861 — picnicking spectators watched the war get suddenly, permanently real; Jackson stood 'like a stone wall' by the Henry House. Second Manassas' Deep Cut a year later was bigger and darker.

• ⚔️Aldie Mill & the Mosby Highway — Aldie

  US 50 is signed the John Mosby Highway: the Gray Ghost's rangers melted in and out of these gaps and hamlets all war. The 1807 twin-wheel mill still grinds on weekends.

• 🏘️Middleburg & Upperville — Middleburg

  Stone-walled horse country strung on the old turnpike — June 1863 cavalry clashes at every crossroads as Stuart screened Lee's march to Gettysburg. The Red Fox Inn has poured since 1728.

Cavalry Country

Warrenton → Orange · ~60 mi

Brandy Station's Fleetwood Hill (the largest cavalry battle in North American history), Culpeper, and Cedar Mountain, where Jackson rallied his line sword in hand.

• 🏛️Mosby's Warrenton — Warrenton

  The Gray Ghost practiced law and is buried here; the Old Jail museum keeps his revolver and the county's stories.

• ⚔️Brandy Station: Fleetwood Hill — Brandy Station

  June 9, 1863: 20,000 horsemen in the largest cavalry battle ever fought in North America. The Graffiti House's plaster still carries soldiers' charcoal signatures from both armies — they billeted in shifts.

• ⚔️Cedar Mountain — Culpeper

  August 9, 1862: Jackson — famously indifferent to gunfire — drew his sword (rusted into its scabbard, the story goes) to rally a breaking line. Preserved fields, walking trail, profound quiet.

The Bloody Quadrilateral

Orange → return · ~105 mi

Wilderness, Chancellorsville, Fredericksburg's stone wall, Spotsylvania's Bloody Angle — and the little plantation office where Stonewall Jackson crossed the river to rest under the trees.

• ⚔️Wilderness: Ellwood — Locust Grove

  May 1864: Grant and Lee's first collision, fought in burning scrub. In Ellwood's little family cemetery stands the war's strangest marker — the grave of Stonewall Jackson's amputated arm, buried a year before the rest of him.

• ⚔️Chancellorsville — Chancellorsville

  Lee's masterpiece, May 1863 — outnumbered two to one, he split his army and sent Jackson crashing through the flank. That night Jackson was shot by his own men in the dark woods; the visitor center stands near the spot.

• ⚔️Fredericksburg's Sunken Road — Fredericksburg

  December 1862: fourteen assaults up Marye's Heights against the stone wall; none got within fifty yards. Chatham Manor across the river hosted Lincoln in better days — then Walt Whitman and Clara Barton beside the surgeons' tables.

• ⚔️Spotsylvania: the Bloody Angle — Spotsylvania

  May 12, 1864: roughly twenty hours of point-blank, hand-to-hand fighting at the Mule Shoe salient — an oak nearly two feet thick fell, cut down by rifle fire alone. The stump is in the Smithsonian; the silence here is total.

• ⚔️Stonewall Jackson Death Site — Woodford

  The plantation office at Guinea Station where Jackson died of his wounds, May 10, 1863 — 'Let us cross over the river, and rest under the shade of the trees.' The clock on the mantel still runs.

Tips and best time to go

• The NPS app's audio tours for all four Fredericksburg-area battlefields are excellent and free.
• Drive the loop counterclockwise to follow the war chronologically (1861 → 1865).
• US 50 west continues to Winchester — handing off to the Valley Pike.

Frequently asked questions

How long is Bull Run to the Bloody Angle and how many days does it take?

Bull Run to the Bloody Angle is about 240 miles and takes 2–3 days at a back-roads pace.

Where does Bull Run to the Bloody Angle start and end?

It is a loop: Loop from Alexandria.

Which highways does Bull Run to the Bloody Angle follow?

It follows US 29, US 50, US 15, VA 3 and US 1.

Which interstate does Bull Run to the Bloody Angle replace?

It avoids I-95 / I-66, using US 29, US 50, US 15, VA 3 and US 1 instead.

How many stops are on Bull Run to the Bloody Angle, and what are the highlights?

11 stops are mapped, including Manassas: Henry Hill, Aldie Mill & the Mosby Highway, Middleburg & Upperville, Mosby's Warrenton and Brandy Station: Fleetwood Hill.

Which ready-made itineraries include Bull Run to the Bloody Angle?

Mosby to the Bloody Angle (3 days), Presidents & Pinot (3 days), The Eastern Crescent (15 days) and The Whole Hog (28 days).

Worth a detour

• Ball's Bluff — Leesburg: a tiny bluff-top national cemetery from an 1861 fiasco that cost a sitting U.S. senator his life and created a congressional committee that hounded generals all war.
• Massaponax Church — Where Grant's staff dragged the pews outside for a council of war — and a photographer on the balcony caught the whole thing, frame by famous frame.
• Kelly's Ford & Germanna — The Rappahannock-Rapidan crossings every campaign fought over; pretty river country now.