Enjoy a One-of-a-Kind Journey on a Coast-to-Coast Roadtrip on US-20
For those who love long road trips, a journey on US-20 is a long, and scenic journey you don’t want to miss. Spanning 3,365 miles from Boston, Massachusetts to Newport, Oregon, this route is the country’s longest highway, taking travelers from big cities like Boston, Chicago, and Cleveland to quaint small towns, past three Great Lakes, iconic spots, and hidden gems.
There’s a lot to see and a lot to do on US-20, so we’ve created an east-to-west 10-day itinerary with tips, sightseeing ideas, and even a few restaurant suggestions as you travel from coast to coast.
NOTE: This is a very long journey to make in 10 days and is meant to provide an overview of various stops along the way. Chances are good that you’ll end up spending a day or two in some cities, so take your time, enjoy the journey, and go at your own pace.
Day 1: Boston, Massachusetts to Albany, New York
Morning
US-20’s eastern terminus is in Boston where Kenmore Square links with MA-2, so start your trip and your day in one of the country’s most historic cities. History buffs can explore historical sites along the Freedom Trail — including Boston Common — and Quincy Market.
The Freedom Trail covers 2.5 miles and takes travelers past 16 historic sites, including the Paul Revere House, the Old North Church, and the site of the Boston Massacre. Boston Common is the country’s oldest public park and Quincy Market is an indoor-outdoor shopping experience with hundreds of shops.
Quincy Market has plenty of eateries, but nearby Faneuil Hall Marketplace also has plenty of breakfast options, including bakeries, burritos, and waffles.
Afternoon
After exploring history around Boston, hop in the car and make your way to Albany — a drive of about three hours. Fair warning, between bigger cities, much of US-20 is a quiet two-lane highway, leaving plenty of time to plan your next steps, listen to audiobooks and radio, or be alone with your thoughts.
You can drive straight through to your destination, but if you like stopping along the way, Great Barrington gives visitors an intimate New England town experience and the Springfield Armory National Historic Site offers a glimpse into the country’s military history.
Evening
Stretch your legs when you reach Albany by exploring New York’s capital city. Ideally, you’ll want to get into town in the mid to early afternoon to see local attractions.
The State Capitol Building is part of the Empire State Plaza on State Street and has stood proud since the 1880s as a marvel of 19th-century architecture. Tours of the capitol are available Monday-Friday at specific times and visitors can also explore memorials on the plaza grounds and a Vietnam Memorial Gallery inside the Abrams Justice Building.
Day 2: Albany, New York to Buffalo, New York
Morning
If you got into town late, set aside time to tour the capital and Empire State Plaza. If you checked that off your bucket list, start your morning at the Albany Institute of History & Art. The museum’s diverse collection of exhibits offers an in-depth look into the history of the Upper Hudson Valley.
You’ve got a long drive ahead of you today, so fill up with a hearty breakfast at Mr. D’s Restaurant & Lounge or Cafe Madison, among many other spots.
Afternoon
Buckle up and grab your shades and snacks as you make your way toward western New York and Buffalo — about a 4.5-hour trip. If you’re keen to stop along the way, this part of the journey takes you through several cities including Utica, Syracuse, and Rochester.
Rochester is a scenic spot on Lake Ontario and travelers can explore the Strong Museum of Play and the George Eastman Museum. In Syracuse, travelers can admire exceptional architecture, and explore unique museums, including the Erie Canal Museum in the historic Weighlock Building.
Shopping enthusiasts can find several shopping centers along their journey, including the Eastview Mall in Victor and the Finger Lakes Premium Outlets in Waterloo.
Wine enthusiasts can find no less than four wineries on the route too, offering a taste and a great view of the Finger Lakes.
Evening
After all that driving, go just a little further — about a half hour — and treat yourself to majestic views of Niagara Falls. The rushing waters of the falls are always a welcome site for travelers of all ages and the feel-good atmosphere is the perfect way to unwind after a long day.
Day 3: Buffalo, New York to Cleveland, Ohio
Morning
Start your morning with some lakefront views of Lake Erie and take some time to visit Buffalo.
One of the city’s most scenic spots is the Buffalo and Erie County Botanical Gardens. Visitors can transform their morning with leisurely walks through a magnificent collection of indoor and outdoor gardens, feed koi fish, and learn plant history from botanical experts.
If you’re heading out in the late morning or early afternoon, make sure to enjoy some of Buffalo’s iconic foods for lunch. The Anchor Bar and Duff’s Famous Wings are two of the most iconic spots for buffalo wings or grab a beef on weck sandwich you can enjoy on the road.
Afternoon
The drive from Buffalo to Cleveland will take around three hours. But the drive goes right along the Lake Erie shore, giving travelers plenty of places to stop and admire the view.
Lighthouse enthusiasts can start with a visit to the Buffalo Main Light and continue with stops including the Dunkirk Lighthouse in Dunkirk, New York, the Presque Isle Lighthouse and North Pier Lighthouse in Erie, Pennsylvania, and the Cleveland Harbor West Pierhead Lighthouse in Cleveland.
Travelers who love hidden gems can detour to the Lucille Ball Desi Arnaz Museum in Jamestown, New York or the Pymatuning Spillway in Linesville, Pennsylvania, where they can feed bread to the large numbers of carp gathered there and watch ducks literally walk on the backs of fish to compete for visitors’ offerings.
Evening
Assuming you’re not sick of listening to music in your car, you can end your day with a trip to the famous Rock and Roll Hall of Fame in Cleveland. Music fans of all ages can explore displays of the most famous musicians of all time, enjoy immersive exhibits, and dive head-first into the history of rock and roll.
Day 4: Cleveland, Ohio to Chicago, Illinois
Morning
You’ve got a long day of driving ahead but, before heading west, stop at Cleveland’s famous West Side Market. It’s Cleveland’s oldest market and offers everything from fresh fruits and vegetables to flowers, spices, and ready-to-eat foods. This is a good spot to get some breakfast and perhaps find something to nosh on during your drive.
Afternoon
Prepare yourself for a long drive — about 350 miles — into the heart of the Midwest and the Windy City, Chicago, Illinois. It’s a lot of driving, but you’ll travel through three states with plenty to see.
Chicago is your final destination for the day, but don’t sleep on sightseeing as you go through Indiana. Shipshewana is a quaint town in the heart of Amish Country in Northern Indiana and offers a delightful look into Amish culture, including Amish stores and cuisine.
Indiana Dunes National Park is an incredibly scenic stretch along Lake Michigan where visitors can hike through the park’s sandy dunes, enjoy beautiful landscapes, or simply enjoy a few moments of quiet surrounded by nature.
Evening
The list of things to see and do in Chicago seems just about endless and could take up its own itinerary, so for time’s sake, we’ll offer just a few ideas.
If you’ve only got an hour or two to get out and see Chicago, the nightlife scene is hopping with many live music spots, including The House of Blues, comedy clubs, and nightclubs.
If you’re keen to stick to attractions, you can’t go wrong with a visit to Millennium Park downtown to see the famous Cloud Gate (The Bean). The park also offers great views of the Chicago skyline, so you can enjoy the last part of your day soaking in a terrific view.
Day 5: Chicago, Illinois to Dubuque, Iowa
Morning
You could spend a day or more in Chicago, but you’ve got to keep moving. Before you go though, visit the iconic Art Institute of Chicago.
It’s been voted Chicago’s top attraction and offers free daily tours and an awe-inspiring range of exhibits. Visitors can see famous works such as American Gothic, Nighthawks, and A Sunday Afternoon on the Island of La Grande Jatte (the painting from Ferris Bueller’s Day Off).
Chicago has many iconic foods, so if you’re hungry before heading out, try an Italian beef sandwich, Chicago-style pizza (deep-dish or tavern style), Chicago-style hot dogs, and even Portillo’s famous cake shakes.
Afternoon
RELATED: If you’re looking for future road trip ideas, historic Route 66 begins on East Adams Street, just west of its crossing with South Michigan Avenue.
Your afternoon drive will take you about three hours from the shores of Lake Michigan to Dubuque in eastern Iowa.
On the way there, you can stop in Galena, Illinois, and explore a “town that time forgot” with a historic downtown, stunning nature sites, and historic homes like the Belvedere Mansion and the Ulysses S. Grant Home.
Evening
Conclude your busy day with a visit to the National Mississippi River Museum & Aquarium. This shrine to the iconic American river is part science center, part museum, and part aquarium that features exhibits on the ecology and history of the Mississippi River.
Once you’ve arrived at your accommodations for the night, relax and pat yourself on the back — you’re halfway through your journey!
Day 6: Dubuque, Iowa to Sioux City, Iowa
Morning
For the first time since you were in New York, you’ll spend the entire day exploring just one state. But you’ll spend a lot of time driving, so fuel up and get a beverage to keep yourself alert.
The day begins with a scenic drive on the Great River Road National Scenic Byway, which stretches the entire length of the Mississippi River from Minnesota to the Gulf of Mexico.
In Iowa, that route covers more than 300 miles, past charming small towns, magnificent bluffs, and plenty of overlooks. A trip to Clinton from Dubuque is a little over an hour and goes along the river. You can turn back and enjoy the same route back to Dubuque before continuing west on US-20.
RELATED: The famous Field of Dreams is about a half hour west of Dubuque in Dyersville and a can’t-miss stop for any diehard baseball fan.
Afternoon
Your afternoon will be spent behind the wheel as you drive in a nearly straight line across Iowa to Sioux City — a distance of about 300 miles. Enjoy views of Iowa farmland and corn fields — after all, you’re in America’s Breadbasket.
Museum-goers can pull off US-20 to explore some of Iowa’s more unique museums.
- Matchstick Marvels Museum in Gladbrook features incredible models made entirely out of matchsticks.
- The Traer Salt and Pepper Shaker Gallery in Traer features more than 16,000 salt and pepper shakers.
- The John Deere Tractor & Engine Museum in Waterloo gives visitors a chance to experience the history of John Deere tractors and engines through fun, interactive exhibits.
Evening
If you spent all day driving, get out, stretch your legs, and visit some of Sioux City’s museums.
The Sioux City Art Center, with its iconic three-storied glass atrium, is home to a unique array of permanent and traveling exhibitions. The Lewis and Clark Interpretive Center presents the Siouxland part of Lewis and Clark’s famous expedition with exhibits, programs, and kids’ activities.
Day 7: Sioux City, Iowa to Casper, Wyoming
Morning
Your morning consists of a long drive through Nebraska and near the South Dakota border — about 500 miles. The good news is you’ll be able to relax once you arrive.
If you like quirky attractions, Carhenge, a replica of Stonehenge made from old cars is worth a detour. The Plainview Klown Doll Museum is also a fun place to stop and has the world’s largest collection of clown dolls.
Afternoon
After all that driving, put on your learning cap as you visit Casper’s National Historic Trails Interpretive Center. Not only does the center offer scenic views of Wyoming, but visitors can also learn about legendary names and everyday pioneers who traveled the Oregon Trail, the Pony Express Trail, and other routes in the 1800s.
Evening
The best thing to do after a long day of traveling and exploring is to kick back and treat yourself to a good Casper meal. FireRock Steakhouse & Grill serves tasty cuts of meat, Racca’s Pizzeria Napoletana slings pasty pies, and Johnny J’s Diner is a fun, relaxed family eatery.
Day 8: Casper, Wyoming to West Yellowstone, Montana
Morning
Start your morning at the Nicolaysen Art Museum & Discover Center — the culture center of Wyoming. The “NIC” offers a look at contemporary art in the high plains and central Rockies and the Discovery Center is a hands-on studio where visitors can wander through vibrant displays.
Afternoon
Another long afternoon drive will take you from Wyoming into Big Sky Country to Yellowstone, Montana — this leg of the trip covers about 350 miles. Enjoy the scenery and get excited for your final destination for the day.
Evening
After a long drive, your US-20 journey brings you to the famous Yellowstone National Park — established in 1872 as the first national park in the United States. Visitors can gaze at the majesty of the Old Faithful geyser, keep their eyes peeled for bears, bison, bighorn sheep, and other wildlife, or hike Mount Washburn.
Day 9: West Yellowstone, Montana to Bend, Oregon
Morning
Yellowstone National Park is such a cool place to visit that you’ll want to go back again before you leave Montana. The Grand Canyon of Yellowstone is a place of stunning natural beauty where visitors can enjoy cascading waterfalls and the site of unique rock formations. A guided tour of Lamar Valley offers the potential to see bison, grizzlies, and plenty more animal activity.
Afternoon
One of the longest drives on your journey will be from Yellowstone to Bend, Oregon — about 600 miles. Hang tight because when you arrive, you’ll be less than a day’s drive from the end of the route. Your afternoon drive will take you through Idaho, where there’s plenty to see.
Highway 20 goes through Idaho for more than 400 miles and passes through Boise and Twin Falls. Visitors can tour the Idaho State Capitol in Boise, see historic buildings at the Old Idaho Penitentiary Site, or even explore contemporary art at the Boise Art Museum.
Evening
Assuming you don’t go to bed right away after such a long drive, take some time to enjoy Bend’s breweries and nightlife. The area has over 30 breweries with numerous award-winning brews that appeal to every tastebud.
Day 10: Bend, Oregon to Newport, Oregon
Morning
You’ve made it more than 3,000 miles and you’re only about four hours from the very end!
Start your morning with one more museum trip, this time to the High Desert Museum. Here visitors can have fun encounters with wildlife, learn about Wild West history, and see beautiful works of art. It’s the perfect way to fill your adventure cup before hitting the road.
RELATED: The last Blockbuster store in the world is also in Bend and sells lots of souvenirs!
Afternoon
One last drive takes you roughly 180 miles from Bend to Newport. Once you reach US-5, you can head south to Eugene or north to Salem for fun detours. But driving straight through will take you to Corvallis, a vibrant college town with plenty to do. Visitors can stroll through the Oregon State University campus, enjoy scenic views along the Willamette River, or shop downtown.
Evening
Congratulations! After all that sightseeing and driving, you’ve finally arrived in Newport, Oregon — the end of US-20. If you want to get to the western terminus, it’s at Newport’s intersection with US-101 near the Pacific Ocean.
Before the sun sets, visit the Oregon Coast Aquarium. Visitors of all ages can connect with Oregon Coast wildlife and learn about both the mysteries of the ocean and ocean conservation.
When you’re done at the aquarium, make your way to Yaquina Head Lighthouse and watch the sunset. You may be tired, hungry, and sore, but you just traveled more than 3,000 miles in 10 days and there’s no better way to cap the trip than with a beautiful sunset.
Enjoy a Memorable Journey Along US-20
Whether it takes you 10 days or 20 to get across US-20, ultimately you’ll enjoy a one-of-a-kind experience seeing some of the most beautiful spots in the US. Use our guide to chart an unforgettable journey from coast to coast and make sure to bring your camera, plenty of good music, and your favorite road trip snacks. Safe travels!