Upper South

States: Virginia

Start near: Richmond (about 1 h 40 min to Charlottesville) · Washington, DC (about 1 h 40 min to Sperryville)

The Constitution Route & 231

Jefferson and Madison's neighborhood, then Virginia's prettiest road

The Constitution Route & 231 is a ~75-mile back-roads route from Charlottesville to Sperryville on VA 20 and VA 231, driven in 1–2 days, that stays off US 29 through the Upper South.

Open the interactive map →

Drive

Charlottesville → Sperryville

Distance

~75 miles

Time

1–2 days

Highways

VA 20 · VA 231

Avoids

US 29

Region

Upper South

Two presidents lived eight miles apart out here, and the road between their houses is signed the Constitution Route. Past Monticello and Montpelier it becomes VA 231 — a US-top-ten scenic byway: stone fences, horse farms and the Blue Ridge wall rising over every pasture, Old Rag's granite dome dead ahead. Wine country the whole way (the Monticello AVA's 40-odd wineries surround the start), ending at Sperryville under Skyline Drive.

📍 The Journey Through Hallowed Ground corridor stacks markers thick here; 231 is a designated Virginia Byway end to end.

The drive, segment by segment

Jefferson's Neighborhood

Charlottesville → Orange · ~30 mi

Monticello's little mountain, ale at Michie Tavern, the Jefferson-designed ruins (and vines) at Barboursville, Gordonsville's fried-chicken history — then Madison's Montpelier, where the Constitution was thought up.

• 🏛️Monticello — Charlottesville

  Jefferson's 40-year argument with a hilltop — the clock, the dumbwaiters, the garden lab, and (told straight now) Mulberry Row, where the enslaved community that ran it all lived. Book the first tour; fog burns off the valley below.

• 🍽️Michie Tavern — Charlottesville

  A 1784 ordinary moved up the mountain — fried chicken and blackeyed peas served by the fire like the stagecoach just left. Touristy and completely worth it.

• 🍷Monticello Wine Trail — Charlottesville

  Jefferson's failed dream, gloriously realized two centuries late: 40+ wineries ring Charlottesville in the Monticello AVA (est. 1984) — Viognier and Cab Franc are the local language. King Family's Sunday polo and Veritas's lawn are the classics.

• 🍷Barboursville Vineyards & Ruins — Barboursville

  Virginia's benchmark winery, planted by the Zonin family in 1976 around the burned-out ruins of a mansion Jefferson designed for Governor Barbour — taste Octagon in sight of the columns. The whole state's wine story in one frame.

• 🍽️Gordonsville — Gordonsville

  The 'Fried Chicken Capital': in the rail decades after the Civil War, Black women known as waiter carriers sold platters of fried chicken through train windows here — entrepreneurship history honored with a festival each spring. The Exchange Hotel by the tracks served as a Civil War hospital; its museum is excellent and haunted, allegedly.

• 🏛️Montpelier — Orange

  James Madison's house, where he spent a year reading a trunkful of books and emerged with the Constitution's architecture. The Mere Distinction of Colour exhibit on the enslaved community is among the best interpretation anywhere.

The 231: Virginia's Prettiest Road

Orange → Sperryville · ~45 mi

Somerset's horse country, Madison's courthouse square, and mile after mile of open pasture running at the Blue Ridge — Old Rag fills the windshield by Banco. Sperryville's galleries and cider close it out at Skyline Drive's doorstep.

• 🏘️Old Somerset — Somerset

  A crossroads of stone walls and horse farms where 231 begins its show — the Madison family's houses dot the fields; the view opens south toward Gordonsville and north to the mountains.

• 🌿Madison & the 231 corridor — Madison, VA

  Madison County calls its stretch a US top-ten scenic byway and the claim holds: open pasture to the Shenandoah ridgeline the whole run. Pull-offs are informal; cows are not impressed.

• 🌿Old Rag View & Banco — Banco

  The granite dome of Old Rag — Virginia's most beloved (and mobbed) summit — owns the horizon; Graves Mountain Lodge below has fed hikers family-style since forever. Apple butter weekends in fall.

• 🏘️Sperryville — Sperryville

  Galleries, a chandlery, copper-pot whisky at the distillery, and Before & After's coffee — a two-block town at Thornton Gap's foot. Skyline Drive starts ten minutes up; the Valley Pike waits over the ridge.

Tips and best time to go

• This route grafts straight onto the Civil War loop at Orange — Cedar Mountain is fifteen minutes from Montpelier.
• October is Virginia Wine Month and peak 231 foliage; book Monticello and tastings ahead.
• Drive 231 northbound in late afternoon: the light rakes the pastures and the Blue Ridge goes violet.

Frequently asked questions

How long is The Constitution Route & 231 and how many days does it take?

The Constitution Route & 231 is about 75 miles and takes 1–2 days at a back-roads pace.

Where does The Constitution Route & 231 start and end?

It runs from Charlottesville to Sperryville.

Which highways does The Constitution Route & 231 follow?

It follows VA 20 and VA 231.

Which interstate does The Constitution Route & 231 replace?

It avoids US 29, using VA 20 and VA 231 instead.

How many stops are on The Constitution Route & 231, and what are the highlights?

10 stops are mapped, including Monticello, Michie Tavern, Monticello Wine Trail, Barboursville Vineyards & Ruins and Gordonsville.

Which ready-made itineraries include The Constitution Route & 231?

Presidents & Pinot (3 days).

When is the best time to drive The Constitution Route & 231?

The atlas’s seasonal note for this route: “October is Virginia Wine Month and peak 231 foliage; book Monticello and tastings ahead.”

Worth a detour

• James Madison Museum of Orange — Hometown miscellany including Madison's own ice house — pairs with the courthouse square.
• Early Mountain & the Madison wineries — The 231 corridor's own tasting rooms — Early Mountain's barn is the area's showpiece pour.
• Skyline Drive (Thornton Gap) — Enter at Sperryville's gap for the ridge-top sequel — 105 miles of overlooks.

Spurs & side-roads

• Montpelier