The Oregon Trail

Driving the Oregon Trail

From the wide-open spaces of the West to the dense urban chaos of the East, this route offers the longest and most involved road trip in Road Trip USA. Connecting an exceedingly diverse range of places and totaling over 3,300 mi (5,311 km)—many more if you count all the potential detours, side trips, and parallel routes—US-20 takes in a little of everything during its two-lane trek from Oregon’s rugged coast to the glorious sea and sand of Cape Cod.

Oregon Trail travel map with Driving Distances between key sights

Superlative sights include at least two wonders of the world, New York’s Niagara Falls and Wyoming’s Yellowstone National Park; the great cities of Boston and Chicago; and two halls of fame, one in Cleveland celebrating rock ’n’ roll, the other in Cooperstown idolizing the national pastime, baseball. Odd museums, classic diners, idyllic towns, and poignant postindustrial decay—you’ll find it all along this great cross-country highway.

Starting in the West, the route parallels, and in places runs right on top of, the broad path that formed the Oregon Trail. The landscape across Oregon, Idaho, and Wyoming along US-20 and a parallel highway, US-26, is still as lonesome as it was more than 150 years ago, when pioneer families followed this one-way route west to the promised lands of the Pacific Coast. Midway across the country you can visit two All-American monuments, Mt. Rushmore and Carhenge.

You also can test the wisdom of Walt Whitman, who wrote, “While I know the standard claim is that Yosemite, Niagara Falls, the upper Yellowstone and the like afford the greatest natural shows, I am not so sure but the Prairies and Plains last longer, fill the aesthetic sense fuller, precede all the rest and make North America’s characteristic landscape.” Drive across the Sand Hills of northern Nebraska on your way past Iowa’s Field of Dreams, and see for yourself what’s so great about the Great Plains.

US-20 crosses the Mississippi River at Dubuque, which, like Galena, on the Illinois side, was one of the oldest settlements on what was once the nation’s western frontier. It then stops off for a look at Chicago before winding east through the newly resurgent, former “Rust Belt” along the Great Lakes. This densely populated region also holds some perfectly preserved historic sites, ranging from rolling Amish farmlands to automobile plants responsible for the country’s classiest cars.

In upstate New York, we follow US-20 across a historical middle ground, between the slow boats of the Erie Canal and the high-speed toll road of the I-90 New York Thruway, winding along the north edge of the lovely Finger Lakes before crossing the Hudson River into the Berkshires of western Massachusetts. The historic Mohawk Trail carries us past Lexington and Concord and into Boston, retracing Paul Revere’s historic ride—in reverse—before following old US-6 to the tip of Cape Cod at the lovely and lively resort of Provincetown, where the Pilgrims really arrived in America, way back in 1620.

Historic Oregon Trail Route

From 1843 until the 1860s, some 400,000 men, women, and children followed this 2,000-mile trail, averaging four months to make the cross-country journey. For more about the pioneer journey, check out our blog post on the Historic Oregon Trail.

Map of the historic Oregon Trail pioneer route

Explore Notable Sights Along the Oregon Trail

Oregon Trail Maps for Road Trippers

Map of the Oregon Trail through Oregon.
Map of the Oregon Trail through Idaho.
Map of the Oregon Trail through Wyoming.
Map of the Oregon Trail through Nebraska.
Map of the Oregon Trail through Iowa.
Map of the Oregon Trail through Illinois.
Map of the Oregon Trail through Indiana.
Map of the Oregon Trail through Ohio.
Map of the Oregon Trail through Pennsylvania and Upstate New York.
Pennsylvania and Upstate New York
Map of the Oregon Trail through Eastern New York.
Eastern New York
Map of the Oregon Trail through Massachusetts.

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