Oregon Trail

Following in the footsteps of pilgrims and pioneers, 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.

Between the Oregon Coast and Provincetown, Massachusetts

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 this book. Connecting an exceedingly diverse range of places and totaling over 3,300 miles—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. 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 post-industrial 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 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 notable 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, including Amish farmlands and the automobile plants responsible for the
country’s classiest cars.

In upstate New York, we follow US-20 across a historical middle ground, in 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.

Cannon Beach, Oregon

Provincetown, Massachusetts