the Old Spanish Trail's middle act
The central act of the old Old Spanish Trail — the 1920s auto trail that ran St. Augustine to San Diego on what became US 90. Before the interstate, this was how America met the Gulf: shrimp boats, live oaks, a lighthouse in the median and five flags' worth of history. From New Orleans it threads the Mississippi Sound's old resort towns, rounds Mobile Bay through a utopian colony, and lands in Pensacola, where Spain planted a colony in 1559 — before St. Augustine, though the hurricane that wrecked it cost Pensacola the bragging rights. (The Trail's Florida and Louisiana acts are their own routes — chain all three for the full US 90.)
📍 Mississippi's coast towns keep dense runs of state historical markers — Bay St. Louis and Ocean Springs reward walking.
Out the old Chef Menteur Highway past Fort Pike, across the Rigolets and into the string of Mississippi Sound towns — Bay St. Louis, Pass Christian, Biloxi — that were the South's seaside playground a century before condos.
An 1820s brick fort guarding the back door to Lake Pontchartrain — the moody, marshy way out of New Orleans that I-10 drivers never see.
A 1922 chitlin'-circuit dance hall — Etta James, Big Joe Turner — still throwing shows in a town that calls itself 'a place apart.'
Cast iron, 1848, and standing in the median of US 90 — it rode out Camille and Katrina and became the coast's comeback symbol. Long tended by women keepers, a 19th-century rarity.
Frank Gehry pavilions under the oaks for George Ohr, the self-declared 'Mad Potter of Biloxi,' whose wild pots America only appreciated fifty years too late.
The hermit genius who rowed twelve miles to Horn Island to paint pelicans through hurricanes. His secret painted room, discovered after his death, is here intact.
Art-town Ocean Springs, the Pascagoula (the 'singing river' of Native legend — and of one very famous 1973 UFO story), then over the delta into Mobile, the original Mardi Gras city — with the Dauphin Island spur hanging south into the bay's mouth.
In 1973, two fishermen reported being floated aboard a craft by clawed beings — one of the most documented UFO cases ever. The city put up a historical marker in 2019. The river already had legends; it sings, after all.
Founded by survivors of the Clotilda, the last known slave ship (1860, fifty years after the trade was banned). The wreck was finally found in 2019; the Heritage House museum tells the community's story.
Mardi Gras started here in 1703 — fifteen years before New Orleans existed, as Mobilians will gladly remind you. Trains, crowns and Joe Cain's whole story.
Mobile's oldest restaurant (1924), home of the upside-down hot dog. Jimmy Buffett name-checked it; locals never needed the endorsement.
The unhurried barrier island at the bay's mouth: Fort Gaines' 1864 ramparts (it was between here and Fort Morgan that Farragut roared 'Damn the torpedoes — full speed ahead!'), the Audubon bird sanctuary where spring migrants make landfall, and the Estuarium's touch tanks.
Fairhope's utopian pier, Point Clear's grand hotel — then choose your beach spur: west down the Fort Morgan peninsula to the 'Damn the torpedoes!' fort (car ferry to Dauphin Island closes the loop), or east through Gulf Shores and Orange Beach to the Flora-Bama. Pensacola collects you either way.
Founded 1894 as a single-tax utopian colony — the experiment technically still runs. Bookshops, flowers on every corner, and the pier at sunset over Mobile Bay.
The star-shaped 1834 fort guarding the bay's throat — the other half of the 'Damn the torpedoes' duel. The little car ferry to Dauphin Island (40 minutes, dolphins frequent) turns the two spurs into the best loop on the coast.
Four miles of undeveloped dune and maritime forest between the condo walls — 'safe harbor' in French, and it is: nesting sea turtles, the Pine Beach trail, and the beach as it looked before 1950.
Alabama's sugar-sand main beach: the Hangout's family sprawl, Gulf State Park's pier and 28 miles of trails — and the hot-pink Pink Pony Pub (1956), the dive that every hurricane has spared.
Home of the Gulf's largest charter fishing fleet, The Wharf's 112-foot Ferris wheel, and back-bay dives reachable by boat — including Pirate's Cove across Arnica Bay, where the floor is sand and the dogs swim.
A full-scale fiberglass Stonehenge hidden in the pines of Barber Marina, with life-size dinosaurs lurking down the road — all by Virginia roadside auteur Mark Cline. Free, weird, perfect.
The honky-tonk that straddles the state line — home of the Interstate Mullet Toss, where thousands hurl dead fish from Florida into Alabama each April. Songwriters' nights are shockingly good.
Free, vast, and the Blue Angels practice overhead most summer Tuesday and Wednesday mornings — locals bring lawn chairs.
A working seafood market the size of a supermarket, bedlam since 1931. Get royal reds. McGuire's Irish Pub nearby has over a million signed dollar bills on the ceiling.
More in the Gulf Coast: The Forgotten Coast · Bayou Teche & the Cajun Prairie · River Road & the Felicianas · US 90: The Florida Backbone · US 90: Rice & Rails · LA 1: End of the Road · Cane River & El Camino Real · Poverty Point & the Delta Parishes