How Did Americans Drive Across the Country Before Highways?

Route 66 was created in 1926 as part of the newly minted U.S. Numbered Highway System, an effort to upgrade America’s interstate roads for the burgeoning automobile age. Before paved highways like Route 66, the idea of driving across the United States was, as the Brooklyn Eagle newspaper described it in 1910, “the last call of the wild.”  

The first cross-country drivers were more like intrepid explorers than road-tripping vacationers. In 1903, a Vermont physician named H. Nelson Jackson made a $50 bet that he and his mechanic, Sewall Crocker, could drive all the way from San Francisco to New York City. 

Without service stations or motels, the two men packed like they were going on safari: a full set of tools, 150 feet of hemp rope, camping and cooking gear, a fireman’s axe, a shotgun and pistols, auxiliary fuel tanks and a single spare tire. It took Jackson and Crocker (and their dog, Bud) 63 days to complete the first successful transcontinental drive in a red 1903 Winton, now housed at the National Museum of American History.

Despite being waylaid for weeks waiting for parts and getting mired in countless mud pits, Jackson and Sewell’s highly publicized drive inspired a generation of intrepid “automobilists” to explore the country by road. And those early cross-country drives—equal parts frustrating and exhilarating—sparked a movement to build a national highway network that eventually included Route 66.  

At the turn of the 20th century, automobiles were an expensive and uncommon luxury, and Americans who wanted to travel from city to city typically did so by train. The only paved roads—bricks, mostly—were confined to the downtown streets of major cities. Once you left the city, rural roads were mostly rutted dirt trails traveled by horse-drawn wagons. When it rained, the already rough roads transformed into impassable quagmires known colloquially as “gumbo.” 

Bicyclists were among the first to lobby for improved road conditions in America. In the late 19th century, wealthy bicycle enthusiasts rallied around the Good Roads Movement, which advocated for better roads in cities and rural areas. Cycling organizations also supported the creation of subscription bike paths for smooth cycling. But of the 2.15 million miles of rural roads in 1904, only 154,000 miles had any sort of pavement, including loose gravel.  

“We’re so used to highways being there and the government paying for them, but that wasn’t the case at all just a few generations ago,” says Brian Butko, author of Greetings from the Lincoln Highway: A Road Trip Celebration of America’s First Coast-to-Coast Highway. 

After Jackson and Crocker’s historic road trip in 1903, “motor touring” became a popular adventure sport for the wealthy, bad roads and all. Wearing protective goggles—windshields weren’t a thing yet—trailblazing automobilists set out from cities to explore the vast American West and tour majestic national parks like Yellowstone and Yosemite.  

“The trails of Kit Carson and Boone and Crockett, and the rest of the early frontiersmen stretch out before the adventurous automobilist,” wrote Colorado attorney Philip Delany about his 1903 road trip from Colorado Springs to Santa Fe.  

Forget GPS—early motorists didn’t even have maps. The author of a 1905 article titled, “Camping Out with an Automobile” recommended going to the library to consult topographical, geographical and survey maps then creating custom road maps using tracing paper. The same article suggested traveling with two cars of the same make and model, so the drivers could share spare parts, since mechanical breakdowns were a major cause of travel delays.

Among the suggested supplies for a cross-country drive were compasses, thermometers, hydrometers (for checking the quality of gasoline), rubber ponchos, tire chains, plenty of guns and ammunition as well as blocks and tackles for hoisting stuck vehicles out of the gumbo.  

Outside of cities, many Americans had never even seen a car at the turn of the 20th century. When one early road-tripper pulled up to a farm to ask for directions, he reported that a small boy “was frightened and commenced to cry violently” at the sight of the loud, dusty contraption.  

By 1912, motor touring had evolved from a hobby into a serious movement to build the first coast-to-coast highways. The American Automobile Association (AAA), formed in 1902, hired a trailblazing (literally) motorist named A. L. Westgard to map of the best cross-country driving routes.  

Westgard, a Norwegian immigrant and mapmaker, was the perfect man for the job. As a charter member of the Touring Club of America, he had already logged more than 4,000 miles in his Midland Pathfinder 40, plotting a passage from New York to California. For the AAA project, Westgard—nicknamed “the Pathfinder”—proposed three routes or “trails” that offered the shortest and smoothest options for a transcontinental drive: 

Westgard’s trail maps were a boon to adventurous motorists, but road conditions could still be sketchy. Because federal and state governments weren’t willing to spend tax dollars improving and paving interstate roads, private associations took up the challenge.  

In 1913, a group of wealthy Midwestern industrialists founded the Lincoln Highway Association to promote the development of the first well-maintained and well-marked transcontinental road. The idea was the brainchild of Carl Fisher, who got rich selling automobile headlamps and was one of the founders of the Indianapolis Motor Speedway. Fisher convinced his auto industry friends (including Frank Seiberling, co-founder of Goodyear Tire & Rubber Company) to pledge millions toward the new highway as an investment in the future of driving.  

“Creating the Lincoln Highway certainly helped their businesses by promoting cars and better roads,” Butko says, “but I really think they also wanted to improve America, to ‘get America out of the mud,’ as they would say.”  

The 3,000-mile Lincoln Highway connected New York City to San Francisco largely following Westgard’s Overland Trail. At first, the route was marked with red, white and blue paint on utility poles, but in 1928, road crews installed 3,000 concrete markers with brass “Lincoln Highway” medallions and arrows pointing the way.

“Something Lincoln Highway drivers would do—mostly wealthy Easterners heading to California—was to dip their tires in the Atlantic Ocean,” says Butko, “and when they made it to San Francisco, they’d dip their tires in the Pacific.”  

Around the same time the Lincoln Highway was established, other private highway associations promoted routes such as the Yellowstone Trail, which eventually stretched from the East Coast to the Pacific Northwest, and the National Old Trails Road, portions of which was later absorbed by Route 66 between New Mexico and California.

In 1915, the “Pathfinder” himself, A.L. Westgard, noted the dramatic improvements in travel conditions in the five short years since he made his first transcontinental drive.  

“Yesterday we had the rough trails with unbridged streams and ravines, rocky and steep hills, deep sand or perchance mud and slush, poor or no accommodations for man or car, motor cars of crude design and unknown weakness,” Westgard wrote, “and Presto! today, overnight, we have well-developed touring routes with fair and fast-improving surface conditions, bridges and culverts, easy grades, plentiful supplies, and well designed, all around dependable cars. Verily, life is decidedly worthwhile, after all.” 

Privately funded cross-country roads like the Lincoln Highway laid the foundation for the advent of the U.S. Numbered Highway System in 1926 and eventually the Interstate Highway System, authorized in 1956.