The longest road in the country travels from Boston, Massachusetts all the way west to Newport, Oregon. U.S. Route 20 is not only the nation’s longest road, but among the most scenic for a road trip.
The route travels across 12 different states, allowing voyagers to explore over 20% of the nation in a straight shot!
How long does it take to drive U.S. Route 20
Despite being the longest road in the nation, traveling cross-country with no stops would take approximately 60 hours to travel all 3,365 miles.
With minimal stops, the trip would more realistically take four days to one week, depending on the number of drivers participating. Often, voyagers traverse U.S. Route 20 over the span of 2-3 weeks, stopping to explore the national landmarks, wildlife, and transforming landscapes across the route!
Road trip from Boston to Newport, Oregon along U.S. Route 20
There are 12 states along U.S. Route 20 and over 100 landmarks to explore across the trip! Find a bit of magic in each state!
Boston
The road begins in Kenmore Square! Key landmarks in this area include Fenway Park, Commonwealth Avenue Malls, and the Charles River Esplanade!
Massachusetts
The road continues west of Boston past local suburbs, the Boston Post Road historic district, and the birthplace of basketball, Springfield!
New York
Traveling through Western and Central New York, the route grazes the Finger Lakes, and is just by the glorious Lake Placid! Niagara falls is just 30 miles off-route.
Pennsylvania
The road continues through several quaint Pennsylvania towns and Presque Isle State Park!
Ohio
A major part of the route, explore Cedar Point Amusement Park, one of the best in the nation for rollercoasters and downtown Cleveland.
Indiana
The route is one of the main roads to Indiana Dunes National Park. Admire the architecture at Notre Dame!
Illinois
The road travels through Chicago, so give yourself plenty of time to explore The Windy City!
Iowa
You’ll cross the historic Mississippi River and get ready for major change of scenery. Trade city skylines for farmland and cornfields galore! Movie buffs will love a look at the Field of Dreams Movie Site.
Nebraska
When you hit Newport, Nebraska, you’ve neared the halfway point of the trip! Here, visit a Stonehenge dupe made from vintage cars, aka “Carhenge.” The state is also filled with wildlife and national parks to explore.
Wyoming
Traveling through the town of Lost Springs, you’ll pass through America’s “least populated municipality.” Travel through mountains at Wind River Canyon, and take side roads to see wild bison and get to Yellowstone National Park—the world’s first national park!
Montana
The route only travels 10 miles of Montana, but enjoy the gorgeous “Going-to-the-Sun Road,” heralded among the nation’s most scenic.
Idaho
Take a 30-minute detour to Blackfoot and visit the state’s Potato Museum, because, when in Idaho! For a a city stop, visit Boise.
Oregon
The final state, but 451 miles to reach Newport, Oregon and complete U.S. Route 20! You’ll travel through both desert, forests, and ocean in this scenic state!
U.S. Route 20 early origins
Two digit route ending in the number zero signify major cross-country highways. In the 1920s, the U.S. Highway system assigned two digit codes to various major coast to coast routes.
Before it was U.S. Route 20, the road was “an American Indian trail early colonists used to travel westward in the 1630s and was later called the Boston Post Road as laid out by Benjamin Franklin to carry mail from New York to Boston,” according to MetroWest Daily News.
