A Short Week
5 days · ~720 miles · from New Orleans
Up the Mississippi's levee roads to Natchez, then all 444 billboard-free miles of the old Trace to Nashville — ten thousand years of footpath at a parkway crawl, one overnight town at a time.
This trip chains: River Road & the Felicianas · Natchez Trace Parkway
Starting in New Orleans, this 5-day itinerary connects River Road & the Felicianas and Natchez Trace Parkway. It suits travellers interested in parks, coast, mountains & water; blues, country, jukes & jamborees; battlefields, the movement & the past. The day-by-day bases let you split roughly 720 miles into a sequence of visits rather than trying to cover every linked route end to end. Use the daily highlights to decide which places deserve your longest stops.
Budget an average of about 144 miles per day across the whole trip, or roughly 3.2–4.8 hours behind the wheel at an assumed 30–45 mph back-roads pace. This is a planning estimate, not a measured time for each leg: transfer days can be longer and rest days shorter. Add meal stops, tours, ferries, traffic and hikes separately; use each day's navigation link for current driving estimates.
Use these day-end areas to plan lodging; the map pins are orientation points, not hotel recommendations. The final day can be your departure day.
Choose your dates around the experiences below rather than assuming one season fits the entire trip. These notes come from the linked route guides; check current forecasts and official schedules.
Leave the city on the River Road: Whitney's sobering tour, Oak Alley's oaks, a plate lunch in the shadow of the levee. Wind up in St. Francisville by dusk — Grace Church's live oaks, a porch on the bluff, the Felicianas going quiet.
The quarter-mile allée of 28 live oaks, planted a century before the 1839 house. The postcard of the Old South — read its slavery exhibit so you see the whole picture.
English Louisiana: Grace Church's mossy churchyard, Rosedown's gardens, and Oakley House, where the young Audubon painted dozens of his birds as a live-in tutor.
The oldest documented plantation house in the lower Mississippi valley (1787) — and a tribunal site after the 1811 German Coast uprising, when hundreds of enslaved people marched on New Orleans. The history is told straight here now.
The one museum on the river told entirely from the enslaved person's perspective (opened 2014) — memorials, first-person narratives, the Wall of Honor. The essential stop on this road; book the timed tour.
Twenty-two cypress slave cabins in an unbroken double row — the most intact plantation landscape in the South, still a working farm. Tarantino shot Django Unchained here, uneasily.
Navigate day 1 in Google Maps ↗ · via Destrehan Plantation, Whitney Plantation, Evergreen Plantation, Oak Alley, Houmas House, Donaldsonville, Louisiana's Two Capitols, Port Hudson
Across the line into Mississippi and up to Natchez by late morning: Longwood's unfinished octagon, the Under-the-Hill saloons, a slow walk of the bluff at sunset. Pick up the Trace's Milepost 0 for tomorrow.
English Louisiana: Grace Church's mossy churchyard, Rosedown's gardens, and Oakley House, where the young Audubon painted dozens of his birds as a live-in tutor.
At the gate of the prison that occupies a former plantation — unsparing history, and the famous (and controversial) October inmate rodeo. LA 66 dead-ends here: 'the end of the road' in every sense.
Jefferson Davis's boyhood home, kept small and plain — a footnote that explains a lot of what follows upriver.
A 1940 roadside restaurant built as a 28-foot hoop-skirted woman; you eat lunch inside the skirt. A complicated icon — repainted, reconsidered, still serving legendary banana caramel pie.
One of the largest Mississippian platform mounds in North America (ca. 1250–1600) — eight acres of engineered earth. Climb at dusk and have it to yourself.
Navigate day 2 in Google Maps ↗ · via Angola Museum, Rosemont, Mammy's Cupboard
The Trace proper: Emerald Mound, the sunken Old Trace where you can walk the original path, Rocky Springs' vanished town. Detour into Jackson for the evening — the Old Capitol, a blue-plate supper, a juke if the night obliges.
One of the largest Mississippian platform mounds in North America (ca. 1250–1600) — eight acres of engineered earth. Climb at dusk and have it to yourself.
Sole survivor of the fifty-odd 'stands' that boarded walking boatmen — straw pallet, cornmeal mush, repeat for 400 miles. The enslaved community that ran it is named and remembered here too.
Two centuries of feet, hooves and wagon wheels wore the path twenty feet down into the loess. Five minutes' walk, total silence, slight chill — the road itself as artifact.
A town of 2,600 reduced by war, yellow fever, the boll weevil and erosion to one brick church and some cisterns in the woods. Free campground; gothic dreams included.
Navigate day 3 in Google Maps ↗ · via Emerald Mound (MP 10.3), Mount Locust (MP 15.5), Sunken Trace (MP 41.5), Rocky Springs (MP 54.8)
The long middle miles north: French Camp's grist mill, the Pigeon Roost and Chickasaw stands, the cypress swamp boardwalk. Roll into Tupelo for Elvis's two-room birthplace and a tamale supper on Main.
A boardwalk loop through tupelo and bald cypress knees — twenty minutes of primordial Mississippi, gators optional.
An 1885 academy village still running; in fall they grind sorghum with mule power. The Council House Café's Mississippi Mud cake is a parkway institution.
One of the highest points in Mississippi — 603 whole feet. Savor the badge; the overlook at sunset is genuinely lovely.
The $180 two-room shotgun house Vernon Presley built; the museum and chapel beside it. Downtown: Tupelo Hardware, where Gladys steered 11-year-old Elvis from a rifle to a $7.75 guitar, and Johnnie's Drive-In's dough burger.
Navigate day 4 in Google Maps ↗ · via Cypress Swamp (MP 122), French Camp (MP 180.7), Jeff Busby Point (MP 193.1)
The prettiest run of all: the double-arch bridge at Franklin, Meriwether Lewis's grave and monument, the Gordon House. The Trace ends north of Franklin — coast into Nashville, ears full of birdsong, for a last night on Lower Broadway.
Eight burial mounds scattered across ninety acres of hay meadow, built around 1–200 CE — older than almost anything else you'll drive past in America.
Sandstone bluffs, fern canyons and a CCC swinging bridge — scenery Mississippi isn't supposed to have, named for the great Chickasaw chief.
George Colbert's stand and ferry over the Tennessee River; legend says the Chickasaw leader once charged Andrew Jackson $75,000 to cross his army. Respect.
FAME Studios (Aretha, Pickett, Etta) and 3614 Jackson Highway, where the Swampers backed the Stones' 'Wild Horses.' Add W.C. Handy's birthplace cabin and Helen Keller's Ivy Green water pump in Tuscumbia — one spur, four shrines.
Grinder's Stand, where the explorer died of gunshots in 1809 — suicide or murder, still argued. His grave's monument is a deliberately broken column: a life cut short.
Navigate day 5 in Google Maps ↗ · via Pharr Mounds (MP 286.7), Tishomingo State Park (MP 304.5), Colbert Ferry (MP 327.3), The Shoals (spur), Meriwether Lewis Site (MP 385.9), Jackson Falls (MP 404.7), Double Arch Bridge (MP 438), Loveless Cafe
The Natchez Trace, End to End is a 5-day trip of about 720 miles.
It starts in New Orleans.
It chains River Road & the Felicianas and Natchez Trace Parkway.
Day 1: near St. Francisville, LA; Day 2: St. Francisville → Natchez; Day 3: Natchez → Jackson; Day 4: Jackson → Tupelo; Day 5: Tupelo → Nashville.