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.

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.

Explore Notable Sights Along the Oregon Trail

• Detour to Columbia Gorge and the Historic Columbia River Highway – Deep, verdant basalt canyon through which the mighty river runs and the oldest scenic route in the country
• Yellowstone National Parks – Packed full of burbling geysers, magnificent canyons, raging waterfalls, and still-wild wildlife
• Mount Rushmore – Equal parts impressive monument and kitschy Americana, Mount Rushmore one of those places you really have to see to believe
• Dyersville: Field of Dreams and the National Farm Toy Museum – Tour the Field of Dreams Movie Site, then see over 30,000 miniature tractors and plows
• Niagara Falls – Venture underneath the falls on the famous Maid of the Mist boat ride or stand on the brink at Prospect Park or Goat Island
• Detour to Cooperstown: National Hall of Fame – See Babe Ruth’s bat, the pair of cracked black leather shoes worn by “Black Sox” player Shoeless Joe Jackson, and rows and rows of bronze plaques naming all the greats of the game
• Boston – Visit the site where Paul Revere set off on his midnight ride or catch a game at Fenway Park

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Oregon Trail Maps for Road Trippers

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