Here's Why Your Next Road Trip Should Be On America's Longest Highway

At 3,365 miles from Boston, Massachusetts to Newport, Oregon, Route 20 is one of the only uninterrupted routes you can still take across America that captures the spirit of an old-fashioned road trip. The two-lane road became a U.S. highway in 1926 and resisted the trend of conversion to a four- or eight-lane superhighways that has affected routes like I-90, I-35, and I-94.

If you drive the entire highway, you’ll pass through Massachusetts, New York, Pennsylvania, Ohio, Indiana, Illinois, Iowa, Nebraska, Wyoming, Montana, Idaho, and Oregon. This gives you a chance to experience an incredible variety of landscapes and environments across the country.

Route 20 will take you through a few of the most dramatic national parks in America. If you’re headed west, the first park you’ll encounter is Indiana Dunes National Lakeshore, which is famed for its stunning waterfront and rolling dunes. The highway will also take you to Yellowstone National Park in Wyoming and through the surreal landscapes of Craters of the Moon National Monument in Idaho. Technically, the highway ends at the eastern entrance of Yellowstone and restarts at the western entrance, but this is only because numbered highways are not designated within national parks.

You’ll start off in Boston and travel west through Albany, New York, passing through places like Toledo, Chicago, Gary, Casper, Sioux City, and Boise. Route 20 is a great path to travel if you’re interested in hitting as many urban attractions on your road trip as possible.

Be prepared to drive through an endless array of small towns with Main Streets that seem stuck in another age. Many spots look almost exactly as they did in the 1950s, like charming Cherry Valley in New York.

A ride down Route 20 has been a classic American road trip for decades. As travel trends continue to change, the era of the great American cross-country car ride might be fading. Explore U.S. Route 20 while you can and make memories that will last a lifetime.