Route 66 may get all the headlines, but U.S. Route 20 is actually the longest road in America! The highway runs from Boston, Massachusetts in the east to Newport, Oregon in the west. That’s 3365 total miles!
Route 20 passes through several big cities (Boston, Cleveland, Chicago) and a bunch of small towns through 12 states. For much of its path between the big cities, Route 20 is a quiet, two-lane road. Taking this road trip gives you a chance to see a great slice of America, from urban centers to rural areas to national parks like Yellowstone!
I’ve personally driven about 75% of Route 20, including the northeast and central portions. If you’re curious about driving any or all of Route 20, this itinerary should be a good starter guide to provide direction and get you on the road.
U.S. Route 20: Map of the Longest Road in America
Here it is. Highway 20, the longest road in the U.S.
Driving Time: 52-60 hours
Note that Route 20 is not considered an interstate, since it’s not a four-lane highway. So it’s not the longest interstate highway in America – that distinction belongs to I-90, which goes from Boston to Seattle and runs parallel to Route 20 across most of the country.
If you’re planning to drive all of Route 20, how much time do you need? Google Maps says the driving time is 52 hours. But with traffic and rest stops, figure more like 60 hours.
Once you factor in all the attractions and cities to visit along the way, you’d want a bare minimum of 12 days to make such a road trip. That’s an average of five hours of driving per day.
However, there’s no reason to rush through a road trip. The journey is the whole point. I’d recommend taking 3-4 weeks if possible, so that you have sufficient time to relax and fully dive into each destination.
Things To See By State
Here’s a guide to some of the coolest things to see in each of the 12 states along the way. Because I’m a fan of kooky roadside attractions, I’ll take special note to highlight some of the quirky spots that are worth pulling over for.
Our road trip will start in the east and move west! We’re also including a few worthy detours when you’ll want to get off Route 20 to check out something cool.
U.S. Route 20 begins on the east in Boston. If you’re not local to the Boston area, definitely take a day or two to check out Bunker Hill and the other historic Revolutionary War sites, including Granary Cemetery, where luminaries like Paul Revere and Samuel Adams are buried.
Route 20 runs for 153 miles through Massachusetts. Boston is the main highlight, but you may also want to Old Sturbridge Village, a living history museum in Sturbridge, or the Naismith Memorial Basketball Hall of Fame in Springfield.
In the western edge of the state near Greenwater Pond in Becket, the Appalachian Trail crosses over Route 20. That’s the perfect place to get out and enjoy a hike!
QUIRKY ATTRACTION: In Springfield, leave Route 20 briefly for your first taste of quirky fun on the trip. Visit the Dr. Seuss National Memorial Sculpture Garden by the Dr. Seuss Museum to see characters like Lorax and Horton the Elephant immortalized in bronze!
Route 20 travels through central New York, starting in the capital city of Albany. See the capitol building and check out a few shops or restaurants before beginning your 372-mile drive through the state.
In New York, the highway travels mostly through small towns. Syracuse and Rochester are two noteworthy cities that are both located less than 20 minutes off U.S. Route 20, so you may consider stopping by there if the quiet countryside isn’t exciting enough.
Sports fans should take the 12-mile detour to visit the National Baseball Hall of Fame in Cooperstown. Also swing over to the town of LeRoy, the birthplace of Jell-O! They have a Jell-O Museum that only costs $5 and features historic Jell-O packaging, advertising, and collectibles.
QUIRKY ATTRACTION: The It’s a Wonderful Life Museum in Seneca Falls is worth a visit if you like quirky museums or you’re really into the classic holiday movie. The museum features photographs and artifacts related to the film. Note the schedule: it’s only open from 11 am to 4 pm, Tuesday through Saturday.
DETOUR OPTION: The most essential New York Route 20 detour is to pass through the city of Buffalo and the iconic landmark of Niagara Falls. From the town of Depew, where Route 20 turns south, Niagara Falls is only 30 miles away. If you’re that close, you’ve got to visit the powerful falls!
Route 20 only spans about 50 miles in the northwest corner of Pennsylvania. This is a fairly busy area, so the highway is four lanes in most of the state.
The main point of attraction here is Erie, the fourth-largest city in Pennsylvania. If you have the time, swing by Presque Isle State Park, a peninsula that juts out into Lake Erie. It’s a great place for picnicking, swimming, and hanging out on the beach. I enjoyed many a family beach vacation in Presque Isle when I was growing up!
At 262 miles, Ohio will eat up a big chunk of your U.S. Route 20 road trip. Devote several hours to Cleveland so you can visit the Rock and Roll Hall of Fame. Other cool things to do in Cleveland include the giant ‘FREE’ stamp downtown, and the A Christmas Story House, dedicated to the famous movie.
In Sandusky, give yourself a full day to experience Cedar Point amusement park. When it comes to roller coasters, I consider Cedar Point the best park in the entire country. I’ve been here many times and they are always adding new thrill rides every year.
DETOUR OPTION: Twenty miles south of Cleveland, you’ll find the often-overlooked Cuyahoga Valley National Park. This place is pretty modest by national park standards – its main draw is a network of hiking and biking trails.
You’ll find a surprising number of Indiana activities on or near Route 20. The highway covers 156 miles in Indiana.
In South Bend, visit Notre Dame University and the impressive Basilica of the Sacred Heart cathedral. Then try the Studebaker National Museum to see a collection of classic cars and even a horse carriage once used by President Lincoln.
Route 20 takes you right to Indiana Dunes National Park, a unique landscape along Lake Michigan. You can climb small sand dunes, go camping, or explore the water.
Just before leaving the state, make a quick pitstop at Michael Jackson’s birth home in Gary.
QUIRKY ATTRACTION: In Elkhart, head up to I-90 to see the RV & Motorhome Hall of Fame. Anybody who enjoys road trips will find this museum fascinating, as it showcases vintage and new campers.
The 234 mile-stretch in Illinois include the biggest city on all of Route 20: Chicago! If you’ve never visited the Windy City, give yourself at least two days to explore.
I lived in Chicago for eight years and I love this city. Personal favorite spots I’d recommend: The Green Mill, an old-time jazz club that has been in business since the days Al Capone used to hang out here; take an architecture boat tour down the Chicago River; and the free Lincoln Park Zoo.
Want some more detour options? Check our list of the 25 most awesome day trips and road trips from Chicago!
Besides Chicago, the biggest Illinois city you’ll encounter on Highway 20 is Rockford, a rust belt city that has been reinventing itself. Grab a meal at a nice restaurant or brewery, then check out the Sock Monkey Statues and Museum.
QUIRKY ATTRACTION: The town of Galena has a cute little business district. They have a statue here of former President Ulysses S. Grant and another of his wife Julia that is sometimes referred to as the Mrs. Butterworth statue because of its unfortunate resemblance. President Grant was the one who in 1872 created Yellowstone National Park, which you’ll be visiting later on this road trip, so stopping here at the home he once lived in is a neat moment of foreshadowing.
After crossing the Mississippi River to leave Illinois, the longest road in America continues into Iowa. Now you’re really entering the heartland of America. Be ready for lots of farmland and cornfields everywhere!
You’ll encounter fun attractions at both far ends of the state. On the east, pass through Dubuque to reach the Field of Dreams movie site in Dyersville. This is the spot where the acclaimed 1989 Kevin Costner movie was filmed. The baseball diamond is still here and you can run the bases if you like!
On the western edge of the state in Sioux City, see the Lewis & Clark Interpretive Site. You’ll be seeing lots of Lewis & Clark historic markers along Route 20, and this is the place to educate yourself about the famous explorers’ journey.
QUIRKY ATTRACTION: In Dyersville, check out the National Farm Toy Museum, which is precisely what it sounds like. All the farm toys you can imagine, from Matchbox cars to plastic tractors to John Deere Barbie dolls, are on display here.
Welcome to Nebraska! A full 423 miles of Route 20 pass through Nebraska, which means you’ll be in this state for quite some time. Fortunately, the state has more unique attractions than you might expect to liven up the journey.
The coolest attraction is Carhenge, the quirky replica of Stonehenge made from old cars. Carhenge requires a 40-mile detour from Route 20, but it’s so worth it!
The Museum of the Fur Trade in Chadron has limited hours but a nice collection of thousands of artifacts related to pioneer life and trading with Native Americans.
QUIRKY ATTRACTION: In the tiny town of Plainview, you’ll find one of the quirkiest attractions I’ve ever visited: The Plainview Klown Doll Museum. This small museum has collected thousands of clown dolls – the largest collection in the world, in fact!
DETOUR OPTION: Mount Rushmore sits 100 miles north of Chadron. That’s a lengthy detour, but the whole point of a road trip is to see the country, right? It makes no sense to pass within two hours of Rushmore and not go up to see those giant heads on the mountain!
The western side of South Dakota has so much to see that it’s worth taking an extra day or two to explore. Besides Rushmore, you can visit Wind Cave and Badlands National Parks and Custer State Park. Keep an eye out for bison!
Heading west into Wyoming, you’ll go through the town of Lost Springs. When I visited Lost Springs years ago, its official population was 1, making it the least-populated municipality in America! However, after the most recent census, it now has a booming population of 4 people.
Continue on to Casper, which has a population of 55,000, making it the largest city on this road trip since way back in Sioux City, Iowa. You’ll probably be desperate for some urban life at this point. Find a brewery or bar for a taste of nightlife and enjoy hanging out in a city that will feel like a thriving metropolis compared to the towns you’ve been passing through over the past several days.
For some history, check in to the National Historic Trails Interpretive Center to learn about the Oregon Trail, Pony Express, and other pioneer trails. Then head up to Cody and the Buffalo Bill Dam Visitor Center.
Have your camera ready as you pass through Wind River Canyon, a scenic byway in which the road is surrounded by mountains.
Finally, the USA Route 20 road trip reaches Yellowstone National Park. Watch the eruption of the Old Faithful geyser, go hiking at Mount Washburn, watch for bears and other wildlife, and visit the “Grand Canyon of Yellowstone” waterfall. This place is magical!
Spend at least a couple days in Yellowstone to truly experience the park. Campgrounds and park lodges are the best places to stay. Be prepared for traffic jams, as the park gets crowded during the summer and people always stop to look at wild animals on the side of the road.
Highway 20 travels through Montana for only 10 miles. There’s not much in this part of the state except the town of West Yellowstone, at the western entrance to the park.
DETOUR OPTION: Montana has such incredible natural beauty. It might be my favorite state in the union. You may want to consider ditching Route 20 after Yellowstone and heading north into Glacier National Park. There, you can drive on one of the most scenic roads in the country, Going-to-the-Sun Road.
This detour will take you several hours away from Route 20, so you’d probably want to continue west to Seattle instead of trying to get back onto Route 20. Here’s a map of what such a detour would look like:
Once you leave Yellowstone, you may start to feel that the best parts of this road trip are behind you. But there’s still some excitement left. Route 20 veers south through Idaho and covers 411 miles.
Boise has a lot of cool places worth checking out. Idaho Falls and Boise are the biggest cities you’ll pass through on the state, and there’s a lot of driving between them. Here, it will really feel like you’re on the longest road in America!
The major attraction in this area is Craters of the Moon National Monument and Preserve. This place is amazing. It’s one of the most fascinating natural wonders of the U.S. that people aren’t familiar with.
Its rocky terrain was created by lava flows that took place pretty recently in geologic terms (the most recent ones occurred around 2000 years ago.) Craters of the Moon has lava caves and tubes to explore, and a number of short but challenging hikes along some of the cinder cones that seem to rise up out of nowhere. There’s no light pollution at night, so it provides clear views of the starry skies.
QUIRKY ATTRACTION: Take the 30-minute detour from Idaho Falls to reach the fun Idaho Potato Museum in Blackfoot! You can pose with the giant baked potato statue outside the museum, then go inside and learn how potatoes are produced and why they became synonymous with the state.
Now we’re almost to the finish line! But getting there will require driving 451 miles across Oregon. The eastern half of the state will take you through the Oregon High Desert, which contrasts with the idea most people have of Oregon as being covered in forests.
That starts to change once you reach Bend, as the Cascade Mountains come into view. Drive 7 miles from downtown Bend to reach the High Desert Museum. Or stay in the city and explore its outdoorsy and cultural activities. And pop in to the very last Blockbuster Video store in the world. It’s still open, and they sell lots of souvenirs!
Finally, you’ll reach that spot where U.S. Route 20 intersects with Route 101, the famous coastal highway that runs from California up to Washington. From there, you can park and walk a few blocks to the ocean. You’ve made it all the way across the country on your Route 20 road trip!
Alternate Route 20 Road Trip: Chicago to Wyoming Loop via the Dakotas
Driving time: 39 hours
A few years back when I lived in Chicago, I decided to undertake a Route 20 road trip west into Wyoming, with a northern loop back home through the Dakotas, Minnesota, and Wisconsin. It was a really cool journey, and I’d recommend it for anyone living in the Midwest.
On this road trip, you’ll hit up all the same spots listed above for Illinois, Iowa, Nebraska, and Wyoming. Plus, you’ll get a chance to visit North and South Dakota, two of the lesser-seen states in this part of the country. Here are some of the additional highlights from taking this loop:
In South Dakota, visit Mount Rushmore as previously suggested. Stop by the Crazy Horse Memorial and learn the strange and unusual story behind that monument that may never be finished. Visit Wall Drug if you like tourist traps. Drive through Custer State Park for the bison and burros, and Badlands National Park for the bighorn sheep and prairie dogs.
Visit Theodore Roosevelt National Park in the western side of the state. In Bismarck, ride the Lewis & Clark Riverboat and check out the unique 19-story state capitol building. Moving east, find the Fargo Air Museum, as well as the National Buffalo Museum in Jamestown. Consider taking your road trip to the Sheyenne River National Scenic Byway.
Most of the excitement in Minneapolis will centered around the Twin Cities of Minneapolis and St. Paul. Stop by one the many beaches on the lakes, and visit the Minneapolis Sculpture Garden or the quirky Mill City Museum. You can spend an entire day at the Mall of America too!
Lastly, passing through Wisconsin on the way back to Chicago provides a chance to spend a day in Madison. You can also visit the wonderfully bizarre House on the Rock, taste some jelly beans at the Jelly Belly Warehouse in Kenosha, and visit the Harley Davidson Museum in Milwaukee.
Whether you complete the full U.S. Route 20 road trip or just drive a portion of the longest road in America, you’ll find lots of interesting places to see. Get out and hit the road!
Are you ready to drive Highway 20 across the country?