Upper South road trips

Shenandoah battlefields, mountain fiddles, bourbon warehouses and the Blue Ridge running like a spine. Valleys where the Civil War never quite ended and the music never stopped.

The Upper South has 31 back-roads routes, about 5,515 miles and 259 curated stops, and 15 ready-made itineraries use them.

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Routes in the Upper South

The Valley Pike
US 11 down the Shenandoah
Winchester → Roanoke · ~200 mi · 2–3 days · skips I-81
Bull Run to the Bloody Angle
The Northern Virginia Civil War loop
Loop from Alexandria · ~240 mi · 2–3 days · skips I-95 / I-66
The Crooked Road
Virginia's mountain music trail
Bristol → Floyd · ~210 mi · 2–3 days · skips I-81
Blue Ridge Parkway & the Smokies
America's longest slow road, southern half
Roanoke → Cherokee (+ Smokies spurs) · ~400 mi · 3–5 days · skips I-81 / I-40 / I-26
Highway 64: Shiloh to Lookout Mountain
Southern Tennessee the long way
Memphis → Chattanooga · ~340 mi · 2–3 days · skips I-40 / I-24
Bourbon, Bluegrass & Shakers
US 68 and the old Kentucky pikes
Lexington → Mammoth Cave · ~180 mi · 2–3 days · skips I-64 / I-65
The Constitution Route & 231
Jefferson and Madison's neighborhood, then Virginia's prettiest road
Charlottesville → Sperryville · ~75 mi · 1–2 days · skips US 29
The Overhill Country
Ocoee whitewater to the peaceful side of the Smokies
Chattanooga → Gatlinburg · ~175 mi · 2 days · skips I-75
Gold, Clay & Longleaf
the Carolina Piedmont crescent
Raleigh → Columbia · ~250 mi · 2–3 days · skips I-85 / I-77
US 11: The Valley Road South
the Great Wagon Road's last act
Roanoke → Bristol · ~150 mi · 1–2 days · skips I-81
Skyline Drive & the Parkway
the Virginia ridgeline, end to end
Front Royal → Roanoke · ~225 mi · 2–3 days · skips I-81 (running parallel below)
Lee's Retreat
the last week of the war
Petersburg → Appomattox · ~110 mi · 1–2 days · skips I-85
The Booth Escape Route
twelve days in April 1865
Washington → Port Royal · ~95 mi · 1 day · skips I-95
US 23: The Country Music Highway
coal seams and gold records
Ashland → Pikeville · ~140 mi · 1–2 days · skips I-64
US 52: The Mine Wars Road
billion-dollar coalfield, five-and-dime pay
Bluefield → Williamson · ~100 mi · 1–2 days · skips I-77 (by a county)
The Midland Trail
US 60 over the New River country
White Sulphur Springs → Charleston · ~120 mi · 1–2 days · skips I-64
The Quiet Zone
no signal, all signal
Lewisburg → Petersburg, WV · ~160 mi · 2 days · skips I-79 (by 60 miles)
The Wilderness Road
Boone's gap and the first West
Bristol → Berea · ~220 mi · 2–3 days · skips I-75 / I-81
Moonbows & the Gorge
Red River Gorge to Cumberland Falls
Slade → Cumberland Falls · ~150 mi · 2 days · skips I-75 (mostly)
US 60: The Mutton Line
Louisville to Paducah the long way
Louisville → Paducah · ~220 mi · 2 days · skips I-64 / the parkways
US 70: Broadway of America
Memphis to Nashville, pre-interstate
Memphis → Nashville · ~210 mi · 2 days · skips I-40
The Middle Tennessee Pike
Franklin to the Shoals on the old roads
Nashville → Muscle Shoals · ~140 mi · 2 days · skips I-65
US 127: The Plateau & the Sale
Sequatchie to York country
Chattanooga → Albany, KY · ~160 mi · 2 days · skips I-40
US 11E: The Great Valley Road
Knoxville to Bristol, statesman country
Knoxville → Bristol · ~110 mi · 1–2 days · skips I-81 / I-26
US 64: The Waterfall Byway
Brevard to Murphy, falling water all the way
Brevard → Murphy · ~120 mi · 2 days · skips I-40 (by 50 miles)
SC 11: The Cherokee Foothills
the peach-shed skyline road
Gaffney → Walhalla · ~115 mi · 1–2 days · skips I-85
The Old Ninety Six District
backcountry crowns and kilns
Augusta → Abbeville · ~100 mi · 1 day · skips I-20
Old Salem to Mayberry
Moravians, Pilot Mountain and Andy
Winston-Salem → Mount Airy · ~70 mi · 1 day · skips I-74
US 58: The Last Capital Road
Martinsville to the Dismal Swamp
Martinsville → Suffolk · ~230 mi · 2 days · skips I-85
The Dragon & the Skyway
Newfound Gap, the Cherohala and US 129: a Smokies loop
Loop from Gatlinburg · ~280 mi · 2–3 days · skips I-40 (by 200 miles)
US 41: Dixie Highway, Nashville to Chattanooga
the old Dixie Highway over Monteagle, with the whiskey dogleg
Nashville → Chattanooga · ~220 mi · 2 days · skips I-24

Ready-made itineraries in the Upper South

Also touches the Upper South: The Whole Hog · Cradle & Surrender: Jamestown to Appomattox

States: Virginia · Tennessee · Kentucky · North Carolina · South Carolina · West Virginia · Alabama · Georgia · Maryland · Washington, DC. Browse the other regions: Gulf Coast · Deep South · Atlantic Coast · Florida Peninsula · Ozarks, Ouachitas & the Bootheel · Beyond the Sabine.

Frequently asked questions

How many Upper South road trips are in the atlas?

31 back-roads routes, about 5,515 miles in all, with 259 curated stops. Every one follows two-lane highways instead of the interstate.

What is the longest route in the Upper South?

Blue Ridge Parkway & the Smokies at about 400 miles (Roanoke → Cherokee (+ Smokies spurs)), a 3–5-day drive.

Which Upper South route works for a weekend?

Old Salem to Mayberry: about 70 miles, 1 day, Winston-Salem → Mount Airy.

Which states does the Upper South cover?

Its routes run through Virginia, Tennessee, Kentucky, North Carolina, South Carolina, West Virginia, Alabama, Georgia, Maryland and Washington, DC.