Road Trip Guides

Ninety miles of cliff-hung coastline where the Santa Lucia Range falls straight into the Pacific. Condors overhead, whales below, and a bridge story around every third curve.

90 miles

Sixteen miles of the road where the Revolution started, and then had to fight its way back to Boston. Every bend, tavern, and stone wall along it has a name and a story.

16 miles

Four hundred forty-four miles with no billboards, no trucks, and ten thousand years of footsteps. A bison path that became the road home for boatmen who floated the Mississippi one way.

444 miles

Six and a half million tons of concrete wedged into a black volcanic canyon, holding back the largest reservoir the country ever built. In August 2026 it fell to the lowest level it has held since the day it started filling.

Limestone hills where the rain does not soak in: it runs off fast into spring-fed rivers, under bald cypress, and into the best swimming holes in Texas. German dance halls, bluebonnets in April, and a river system that demands respect.

Four hundred sixty-nine miles strung between two national parks like beads on a string, exactly as its designer meant it. The most visited unit in the entire National Park System, and in places still recovering from the worst flood damage it has ever taken.

469 miles

One hundred thirteen miles and forty two bridges laid over the ruins of Henry Flagler's railroad, with nothing on either side but water most of the way. It ends at a buoy that is not quite as far south as it claims to be, which is the most Key West fact there is.

113 miles

Three days in July 1863 left more than fifty thousand casualties and over thirteen hundred monuments on the same square miles of Pennsylvania farmland, more outdoor sculpture than almost anywhere else on earth. The roads that connect them are laid out to be driven in one direction, and this is that direction.

The longest unbroken stretch of the Mother Road left anywhere: the one the interstate never buried, just quietly walked away from. Neon signs, a Hualapai reservation town, the barbershop that inspired a Pixar movie, and a mountain pass so severe that drivers once paid locals to take the wheel.

Two hundred markers over the flat cotton country where the blues was invented, then carried north up Highway 61 until it turned into rock and roll. Dockery Farms, a filling station crossroads, the last of the juke joints, and three separate graves for one man.

A French grid rebuilt by the Spanish, filled by Africans and Caribbean refugees, and sold to the United States in a room off Jackson Square. Park once and walk the Quarter, then drive the neighborhoods that actually made the music.

Railroad, silver and coal fortunes stacked marble palaces along one avenue above the Atlantic, then called them cottages and used them six or eight weeks a year. Tour the grandest of them, and walk the public path that still runs beneath their lawns.