Jackson, MS; Natchez, MS; New Orleans (283 Miles)
The first four segments of our great Southern road trip have brought us all the way from the South Carolina coast to central Mississippi (with no shortage of meandering detours along the way). And now, after bidding Jackson, Mississippi, farewell with an early lunch of pot roast and bacon-flecked green beans at the city's oldest restaurant, the Mayflower Cafe (mayflowercafems.com), we set out to travel one of America's oldest roads. The Natchez Trace Parkway (nps.gov/natr) runs roughly parallel to the Natchez Trace, a 440-mile footpath that was first trod by prehistoric animals, with Native Americans, European explorers, and now my travel buddy Tim and me following in their footsteps. For miles, the winding route is free of other cars, and as we pass turnoffs for waterfall hikes, ancient ceremonial mounds, and historic way stations, it feels like we're on our own private road.
A little less than two hours later, we arrive in Natchez, Mississippi, where the Trace ends at the edge of the mighty Mississippi River. There, a narrow sliver of riverbank lined with wood-frame storefronts makes up the city's Under-the-Hill, where the first settlement was built in 1716 and which became a haven for gamblers, goodtimers, and good-for-nothings after the more respectable "upper town" was built post-Revolutionary War. A tamer version of that history persists, in the Under the Hill Saloon (underthehillsaloon.com), with Patsy Cline drifting out the doors, and the newest arrival, The Camp (601/897-0466), a craft beer joint that opened on the Silver Street strip in May. At nearby Magnolia Grill (magnoliagrill.com), where you can see the water from every seat in the house, we dine on blue cheese-topped burgers and sweet potato fries.
Next, we join tours of two of the city's 11 antebellum mansions—most built as homes for local politicians, lawyers, and cotton merchants—that open their doors to visitors year-round. Rosalie Mansion (rosaliemansion.com), an 1823 Greek Revival with unbeatable bluff-top Mississippi River views, served as a model for many later mansions across the South. Inside, it's all ornate carpets, marble mantelpieces, and Rococo furniture. And at the dome-topped Longwood (601/442-5193), which would have been America's largest octagonal house had the Civil War not halted construction after only the ground-level "basement" was completed, you can still see the builders' abandoned tools in the second floor workshop and peer 100 feet up into the unfinished cupola, through a swirling bird's nest of overlapping cypress beams.
After the tours, we set the GPS for New Orleans and settle for a car-window view of the antiques shops along Natchez's Franklin Street in order to get a leg up on the three-hour drive. The light-dappled roads look tiger-striped as we wind through Homochitto National Forest, but the scenery gets a little less poetic (more traffic, more taillights) as we approach NOLA. Our payoff for navigating rush hour comes when we check in at the Windsor Court Hotel (windsorcourthotel.com; rooms from $180), a luxe, 316-room property fresh off a $22 million restoration (including a swanky new 4,500-square-foot spa, marble baths, and custom toile wall coverings). Frankly, it'd make even those wealthy Natchez cotton merchants a little green. We splurge on dinner at Pêche Seafood Grill (pecherestaurant.com), a hybrid raw bar/wood-fired grill from a trifecta of top Louisiana chefs (Donald Link, Stephen Stryjewski, and Ryan Prewitt). And after a single round of the bartender's potent 3rd Ward Rougaroux, made with two kinds of rum, hazelnut liqueur, pineapple, and lime, we're delighted that the restaurant's a mere 10-minute walk from our hotel.
New Orleans (10 Miles)
There's something about morning in New Orleans, when the sidewalks are still wet from being cleaned, the light is just starting to filter through the ferns that hang from the French Quarter balconies, and you can make a game of guessing who among your fellow travelers rose bright and early and who's been up all night. Especially at Café Du Monde (cafedumonde.com), the open-air landmark (since 1862) where there are essentially only two items on the menu: coffee and beignets, both served 24 hours a day. The chewy, dense mounds of fried dough come three to a plate and piled high with drifts of powdered sugar. As Tim and I divvy up the last one, a trumpet player begins a rendition of "Amazing Grace," while other diners wipe sleep out of their eyes—and sugar off the tips of their noses.
We've set aside the rest of the day for wandering, and start by browsing the paperbacks and 19th-century botanical etchings at Crescent City Books (crescentcitybooks.com), then head to the galleries and antiques shops along Royal Street. There's a whole wild world to be found—namely, Chris Roberts-Antieau's taxidermy deer heads in elaborately embroidered masks at Antieau Gallery (antieaugallery.com) and Lisa Brawn's colorful woodcuts of native Louisiana birds at Tresor Gallery (tresorgallery.com). And the indigenous street life is pretty exotic, too—we pass sidewalk musicians in all manner of plumage (from green-haired groups in well-worn rags to a solo slide-guitarist in a smart gray suit). The Quarter's dreamy 18th-century architecture, with its pastel facades and romantic ironwork, however, always threatens to steal the show.
We head to Mid-City to Emeril alum Isaac Toups' contemporary-Cajun joint, Toups' Meatery (toupsmeatery.com). Ordering only from the lengthy à la carte section, we assemble a hearty spread—an order of fried, pickle-topped boudin balls, house-made garlic-pork sausage, and the addictive cracklins (which can be bought, along with a pint of beer, in a to-go cup). It's lucky that the 1,300-acre City Park (neworleanscitypark.com) is just two blocks away, because we're in dire need of a constitutional after all that carnivory. Along with 60 acres of forest, a 12-acre botanical garden, and the New Orleans Museum of Art's Sydney and Walda Besthoff Sculpture Garden (noma.org), the park is home to one of the world's largest groves of mature live oaks, some of which first sprouted leaves 600 years ago.
For dinner, we hit up Cane & Table (caneandtablenola.com), a dimly lit and elegantly decayed, tiki-tinged craft cocktail spot on Decatur Street—the one unmarked exception to the rest of the block's rowdy bars and their gaudy signs. The light-as-air Florida Natural cocktail (made with orange-and-cardamom shrub and sparkling wine) is the perfect complement to the fiery, crispy, fried rum ribs, topped with papaya chutney and a thick layer of sambal. From there, it's a short stroll to Frenchmen Street, where the weekend Frenchmen Art Market (frenchmenartmarket.com) has set up in a light-strung lot across from a row of music clubs. Practically every establishment has its doors thrown open wide to let loose the sounds of live jazz and blues. Tim and I duck into d.b.a. (dbaneworleans.com) for a set by the Shannon Powell Trio, which briefly becomes a foursome when the band welcomes a blond British tourist on stage to belt out a couple of tunes—proof positive that this town's anything-goes ethos isn't just about boozing in the streets and flinging beads, but also friendliness, flexibility, and a knack for artful improvisation.
New Orleans (5 Miles)
It's felt like a whirlwind of a visit to New Orleans, so it's fitting that the front desk staff at Windsor Court Hotel directs us to the Ruby Slipper Cafe (therubyslippercafe.net), two blocks away, for our final breakfast. Under other circumstances, my plate of Bananas Foster Pain Perdu would've sent me right back to bed for a nap, so instead of getting behind the wheel right away, we stall. The genius plan: Let the city drive for us! We board a St. Charles Streetcar (norta.com) for an impromptu cruise through the Garden District. It's hard to think of a better use of $1.25 as we take in all the stately 19th-century homes and eavesdrop on the chatter of tourists bound for Jazz Brunch at Commander's Palace (commanderspalace.com) and locals gossiping about the conductor throughout their unconventional commute. One thing we do know for sure as the antique car sways along its track: We're just happy to be along for the ride.