Oregon Trail on US 20 Road Trip Itinerary
Take a journey along the Oregon Trail on US 20 Road Trip! This 5426km route, starting in Boston and ending in Astoria, will give you the chance to explore the best of the United States. Along the way, you'll pass through Albany, Buffalo, Chicago, Sioux City and Casper. Each of these towns have their own attractions and sights to see, such as the historic sites of Albany, the iconic architecture of Chicago, and the beautiful scenery of Casper. The best time of the year to drive this route is during the summer months, when you can enjoy the excellent road conditions and the warm weather. With a recommended time of 21 days, this road trip provides a very high level of experience and memories, and is suitable for all drivers. You can manage the route on a moderate budget, making it the perfect way to explore the US.
21
number of days
5,426 km
route length
fair
budget
tourist
good for
on the right
traffic direction
moderate
accident level
START
Boston
Distance 5,426 km
Driving time 70.1 h
Pace: fast
1,627.7 kWh
Airports
BOS
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Boston is a vibrant and historically rich city, located in the northeastern United States. It is an ideal starting point for the Oregon Trail on US 20 Road Trip. There are plenty of interesting sights to explore and activities to do in Boston.
Visitors can explore the Freedom Trail, a 2.5 mile-long path that winds through the streets of downtown Boston and highlights important landmarks in American history. Other must-see spots include the USS Constitution Museum, the Museum of Fine Arts, Fenway Park, and the New England Aquarium. For a unique experience, take a whale watching tour off the coast of Boston.
Travellers arriving by air can fly into Logan International Airport (IATA: BOS). Car rental services are available at the airport, and there are plenty of rental car options to choose from. Drivers will find the roads easy to navigate and the scenic views along the way make for a great road trip.
Boston is a great place to start the Oregon Trail on US 20 Road Trip. With a variety of activities and attractions, visitors are sure to have an unforgettable experience in this amazing city.
1
Boston
- Albany
Distance 315 km
Driving time 6.2 h
Pace: modest
81.9 kWh
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Are you ready for an exciting road trip from Boston to Albany? This 196-mile journey will take you less than 7 hours to complete and will be full of fun and interesting sights.
Start your adventure in Boston and make sure to visit the Freedom Trail, a 2.5-mile path that will take you to 16 historical sites. Then, take a stroll in the beautiful Boston Common, the oldest public park in the United States.
Continue your trip to Albany and explore the New York State Capitol building, the seat of government of New York. Admire its impressive architecture and learn about its history. Don't forget to visit the Empire State Plaza, a large government complex with impressive modern architecture.
On your way back, make sure to stop by the Saratoga National Historical Park, where you can learn about the Battle of Saratoga, one of the most important battles of the American Revolution.
This is just a small taste of what you can experience on your journey from Boston to Albany. For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, you can find it in the Itinerary of this stage. So what are you waiting for? Pack your bags and hit the road!
Albany - United States - North America - Road Trip - Wikimedia Commons
Albany - United States - North America - Road Trip - Wikimedia Commons
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2
Albany
- Auburn
Distance 250 km
Driving time 3.5 h
Pace: fast
74.9 kWh
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Are you ready for the ultimate road trip experience? Start your journey in Albany, United States, and make your way to Auburn through a 155mi drive that will take you less than 4 hours. Your first stop should be the Corning Tower, the 42-story skyscraper that is one of the tallest buildings in the state. After that, you can visit the New York State Museum and explore its vast collections of art and history. For a more interactive experience, don't miss the interactive exhibits at the Albany Institute of History and Art.
Once you reach Auburn, you can visit the Seward House Museum, a stately mansion built in 1816. Here, you can learn about the life of William H. Seward, who served as the Secretary of State under Abraham Lincoln. You can also take a stroll in the Harriet Tubman Home, the site of the former residence of the famous abolitionist.
Finally, make sure to visit the Willard Memorial Chapel, an historic church built in 1873. The chapel is filled with stained glass windows and a magnificent pipe organ.
More information regarding attractions, accommodation options, recommended restaurants, and campsites along the route is available in the "Itinerary" of this stage. So, what are you waiting for? Start planning your road trip today!
Auburn - United States - North America - Road Trip - Wikimedia Commons
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3
Auburn
- Buffalo
Distance 217 km
Driving time 3.2 h
Pace: fast
65.1 kWh
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Welcome to one of the most interesting road trips in the United States! Starting in Auburn, you will drive through the picturesque landscapes of Niagara Falls and end in Buffalo. Along the way, you can explore historical sites, beautiful natural attractions, and unique parks. The driving distance is 135 mi and it will take you less than 4 hours to get to Buffalo.
On your way, you will pass through Niagara Falls, where you can visit the majestic Horseshoe Falls, the American Falls, and the Bridal Veil Falls. You can also take a boat tour to get a closer look at the falls and learn about the local flora and fauna.
In Buffalo, you can explore the city's rich art and culture scene. Visit the Albright-Knox Art Gallery, the Buffalo and Erie County Botanical Gardens, and the Buffalo Zoo. If you're looking for a great view of the city, take a ride on the SkyWheel.
As you travel, take in the stunning natural beauty of the area and make sure to stop at some of the most picturesque spots. You can also find out more about the local history, culture, and attractions by visiting the local museums and galleries. For more information about the attractions, accommodation options, recommended restaurants, and campsites along the route, check out the Itinerary of this stage.
Enjoy your journey!
Buffalo - United States - North America - Road Trip - en.wikipedia.org
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4
Buffalo
- Cleveland
Distance 319 km
Driving time 5.8 h
Pace: modest
82.9 kWh
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Are you ready to embark on an exciting road trip from Buffalo to Cleveland? This 198-mile stretch of road will take you through Lake Erie and is sure to be an unforgettable experience.
Start your trip in Buffalo, the second-largest city in New York State. Here, you can explore the Buffalo and Erie County Botanical Gardens, take in the stunning views of Niagara Falls, and visit the Buffalo Zoo.
Next, you’ll be driving along Lake Erie, one of the five Great Lakes. Stop at the Lake Erie Islands for a day of sunbathing, swimming, and fishing. You can even take a ferry to some of the islands and explore the wildlife.
Finally, you’ll arrive in Cleveland, the second-largest city in Ohio. Here, you can explore the Cleveland Museum of Art, the Rock and Roll Hall of Fame, and the Cleveland Metroparks Zoo.
This road trip can take as little as 6 hours, so you’ll have plenty of time to explore the sights and sounds of these amazing cities. For more information on attractions, accommodation options, recommended restaurants, and campsites along the route, check out the Itinerary of this stage.
Cleveland - United States - North America - Road Trip - pxhere.com
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5
Cleveland
- Chicago
Distance 551 km
Driving time 5.6 h
Pace: fast
165.3 kWh
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Welcome to your road trip from Cleveland to Chicago! This 342-mile journey is sure to be an exciting one, with plenty of interesting sites to explore and discover along the way. Start off your trip by visiting the Rock and Roll Hall of Fame in Cleveland, where you can learn about the history of rock music and see some of the most iconic artifacts in the industry. Then, make your way to the Cleveland Museum of Art, which houses a vast collection of artwork from around the world.
As you drive further, you will pass through some of the most stunning countryside in the Midwest. Once you reach Toledo, be sure to check out the Toledo Zoo, one of the oldest zoos in the country. As you continue your journey, make a stop in Fort Wayne to explore the Fort Wayne Children's Zoo, home to over 1,000 animals.
Finally, you will arrive in the Windy City of Chicago. Here, you can visit the Art Institute of Chicago, which is home to some of the most impressive artworks in the world. You can also take a stroll along the Magnificent Mile, a stretch of Michigan Avenue that is lined with some of the city's most iconic stores and restaurants.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, be sure to check out the Itinerary of this stage. Enjoy your road trip from Cleveland to Chicago!
Chicago - United States - North America - Road Trip - www.goodfreephotos.com
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6
Chicago
- Dubuque
Distance 290 km
Driving time 3.3 h
Pace: fast
86.9 kWh
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Are you ready for a road trip from Chicago to Dubuque? Get ready to explore the beautiful Midwest region! This stage of the journey is only 180 miles, so you can make it in less than 4 hours.
Your first stop should be the Magnificent Mile in Chicago, the city's most famous shopping street. Here you can find a variety of stores and restaurants. Then, you can explore the Lincoln Park Zoo and its wide variety of animal species.
Once you leave Chicago, you will drive through the countryside of Illinois and Wisconsin, passing through small towns like Freeport and Galena. Make sure to stop at the Galena Cellars Vineyard and Winery, where you can sample some of their award-winning wines.
Your final destination is Dubuque, Iowa, a city located on the banks of the Mississippi River. Here you can visit the National Mississippi River Museum and Aquarium and learn about the history of the river. You can also explore the historic downtown area, with its many restaurants, shops, and galleries.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please visit the "Itinerary" of this stage. Have a great trip!
Dubuque - United States - North America - Road Trip - en.wikipedia.org
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7
Chicago
- Sioux City
Distance 490 km
Driving time 4.9 h
Pace: fast
147.1 kWh
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Are you ready for your next road trip? Start your journey in Chicago, United States and end in Sioux City. On your way, you will have the chance to visit some of the most interesting places.
In Chicago, you could visit the Navy Pier, the iconic Ferris Wheel, and the Art Institute of Chicago. Take a break and enjoy the view of the city from the skydeck at the Willis Tower.
Once you leave Chicago, the next stop is in Rockford, Illinois. Visit the Anderson Japanese Garden, a 12-acre Japanese garden, and the Tinker Swiss Cottage Museum and Gardens.
The next stop is in Madison, Wisconsin. Visit the Wisconsin State Capitol and the University of Wisconsin–Madison.
After Madison, you will arrive in La Crosse, Wisconsin. Visit the Grandad Bluff Park, the Mississippi River and the Riverside Park.
The last stop of your road trip is in Sioux City, Iowa. Visit the Sergeant Floyd River Museum and Welcome Center, the Sioux City Art Center, and the Stone State Park.
This 305 mi journey will take you less than 5 hours drive. More information about attractions, accommodation options, recommended restaurants, and campsites along the route is available in the "Itinerary" of this stage. So, what are you waiting for? Start your road trip now!
Sioux City - United States - North America - Road Trip - Pikrepo
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8
Sioux City
- Valentine
Distance 380 km
Driving time 4.0 h
Pace: fast
114.0 kWh
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Welcome to the Sioux City to Valentine road trip stage! This amazing 236mi journey will take you less than 4 hours and will give you the chance to visit some of the most iconic places of the area.
In Sioux City, you should definitely visit the Dorothy Pecaut Nature Center, where you can explore the wonders of nature and take part in educational programs. The Sergeant Floyd River Museum & Welcome Center is also a must-see, as it offers an insight into the history of the area.
Your next stop is in O’Neill, where you can visit the O’Neill Country Club, a great place to practice your golfing skills. The O’Neill City Park is also worth a visit, as it offers a great opportunity to relax and enjoy the beauty of nature.
The next stop is in Valentine. Here, you should visit the Fort Niobrara National Wildlife Refuge, which is home to a wide variety of wildlife. You should also visit the Smith Falls State Park, which offers a great opportunity to enjoy the beauty of nature.
This is one of the stages of a larger tour, and more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route is available in the "Itinerary" of this stage. So, don't wait any longer and enjoy this incredible road trip!
Valentine - United States - North America - Road Trip - Wikipédia
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9
Valentine
- Casper
Distance 520 km
Driving time 5.4 h
Pace: fast
155.9 kWh
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Are you ready for an amazing road trip from Valentine to Casper? This 323-mile journey is sure to be an unforgettable experience! With an estimated driving time of fewer than 6 hours, you'll have plenty of time to explore the best of these two cities.
Start your journey in Valentine, where you can visit the Niobrara National Scenic River, where you can take a canoe trip, go fishing, or explore the banks of the river. Then, drive to the iconic Chimney Rock National Historic Site, a towering spire of rock that stands out against the skyline.
Next, head to Casper and make sure to stop at the National Historic Trails Interpretive Center, where you can learn about the history of the Oregon, California, and Pony Express Trails. Then, take a stroll through the Fort Caspar Museum and Historic Site, where you can learn about the area's history and explore the old fort.
Finally, don't forget to visit the Casper Planetarium, where you can explore the night sky with interactive exhibits and a state-of-the-art digital projector.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please refer to the "Itinerary" of this stage. Have a great road trip!
Casper - United States - North America - Road Trip - www.nps.gov
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10
Casper
- Cody
Distance 345 km
Driving time 3.8 h
Pace: fast
103.5 kWh
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Are you up for an amazing road trip from Casper to Cody? This 214mi journey will take you less than 4 hours to complete and it’s one of the stages of a larger tour. On your way you can visit the National Historic Trails Interpretive Center, the Tate Geological Museum and the Casper Planetarium. In Cody you can explore the Buffalo Bill Center of the West, the Old Trail Town and the Cody Nite Rodeo.
At the National Historic Trails Interpretive Center you can learn more about the Oregon, California and Mormon Trails. The Tate Geological Museum is a great place to learn about the geology of Wyoming, while the Casper Planetarium offers a great stargazing experience.
In Cody, you can explore the Buffalo Bill Center of the West, which has five museums in one, and the Old Trail Town, which is a collection of over 30 original buildings from the Old West. Last but not least, the Cody Nite Rodeo is a great place to watch a rodeo show.
For more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route, please check the "Itinerary" of this stage. So, what are you waiting for? Start planning your Casper to Cody road trip today!
Cody - United States - North America - Road Trip - commons.wikimedia.org
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11
Cody
- Idaho Falls
Distance 389 km
Driving time 5.1 h
Pace: fast
116.7 kWh
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Welcome to an exciting road trip stage starting in Cody, United States and leading through Yellowstone National Park and Idaho Falls! This 242-mile journey can be completed in fewer than 6 hours and is full of amazing attractions and beautiful views.
Start your adventure in Cody and visit the Buffalo Bill Center of the West, where you can learn about the history of the Wild West and admire the art collections. Then, drive to Yellowstone National Park and explore its many wonders. Don’t miss the chance to see the Old Faithful geyser, the Grand Canyon of the Yellowstone, and the Mammoth Hot Springs.
Continue your journey to Idaho Falls and explore the city’s many attractions, such as the Museum of Idaho, the Idaho Falls Zoo, and the Idaho Falls Greenbelt.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please check the Itinerary of this stage. Have a safe and enjoyable journey!
Idaho Falls - United States - North America - Road Trip - Wikimedia Commons
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12
Idaho Falls
- Boise
Distance 412 km
Driving time 4.3 h
Pace: fast
123.7 kWh
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Are you ready to take on one of the most beautiful road trips in the US? Starting in Idaho Falls and ending in Boise, this 256mi journey will take you no more than 5 hours. Along the way, you will have the chance to explore some of the most interesting places in Idaho.
In Idaho Falls, you should definitely visit the Museum of Idaho, where you can learn about the local history and culture. You should also take a stroll through the Idaho Falls Greenbelt, a beautiful park that follows the Snake River.
On your way to Boise, you should make sure to stop in Twin Falls, where you can marvel at the Shoshone Falls and the Snake River Canyon. You can also visit the Snake River Birds of Prey National Conservation Area, where you can observe some of the most beautiful birds in Idaho.
Finally, in Boise, you should visit the Boise River Greenbelt, a 25-mile stretch of riverside trails and parks. You can also explore the Boise Art Museum, where you can admire some of the most interesting artworks in the US.
This is just one part of a larger tour, and more information about attractions, accommodation options, recommended restaurants, and campsites along the route is available in the “Itinerary” of this stage. So, what are you waiting for? Get ready for an unforgettable adventure!
Boise - United States - North America - Road Trip - Good Free Photos
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13
Boise
- Bend
Distance 513 km
Driving time 5.9 h
Pace: fast
154.0 kWh
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Welcome to the Boise-Bend road trip stage! This trip is about 319 miles long and it should take you fewer than 6 hours to get to Bend.
Start your trip in Boise, the capital of Idaho. Make sure to visit the Boise River Greenbelt, a 25-mile long path along the river, and the Idaho State Capitol Building, a historic building with a neoclassical style.
Then, drive to Mountain Home and visit the Anderson Ranch Reservoir, a beautiful lake surrounded by mountains.
Continue your journey to Sun Valley, a beautiful mountain resort. Take a hike in the Sawtooth National Forest and enjoy the stunning views of the area.
Finally, reach Bend, a city in the high desert of Central Oregon. Visit the High Desert Museum, the Deschutes River Trail, and the Pilot Butte State Scenic Viewpoint for stunning views of the city.
More information regarding attractions, accommodation options, recommended restaurants, and campsites along the route is available in the "Itinerary" of this stage. Enjoy your trip!
Bend - United States - North America - Road Trip - commons.wikimedia.org
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14
Bend
- Portland
Distance 265 km
Driving time 3.4 h
Pace: fast
79.5 kWh
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Welcome to the Bend-Portland road trip! This tour takes you on a scenic journey of 165 miles through some of the most beautiful parts of Oregon. The drive will take you around 4 hours, so you'll have plenty of time to enjoy the sights and sounds of the area.
Start off your trip in Bend, where you can explore the city's unique culture and outdoor activities. While in Bend, be sure to visit the High Desert Museum, the Deschutes River Trail, and the Old Mill District.
Continue your journey to Portland, where you can find a variety of attractions, including the Portland Japanese Garden, the International Rose Test Garden, and the Pittock Mansion.
As you travel along the route, be sure to keep an eye out for historical sites and other interesting points of interest.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, be sure to check out the "Itinerary" of this stage.
We hope you enjoy your Bend-Portland road trip!
Portland - United States - North America - Road Trip - Wikipedia
Portland - United States - North America - Road Trip - Wikimedia Commons
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15
Portland
- Astoria
Distance 171 km
Driving time 5.6 h
Pace: slow
39.2 kWh
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Are you ready for an amazing road trip? Portland to Astoria is one of the most beautiful routes in the US. The 106mi journey will take you less than 6 hours and you will be able to visit some of the most interesting places in the Northwest.
Start your journey in Portland and make sure to visit the iconic Washington Park, the International Rose Test Garden, and the Oregon Zoo. After that, hit the road and drive up the Columbia River Gorge. Stop to admire the stunning Multnomah Falls and the Bonneville Dam.
Continue your journey to Astoria, the oldest American settlement west of the Rockies. Here you can visit the Flavel House Museum, the Astoria Column, and the Astoria Riverwalk. Don't forget to take a stroll through the charming downtown and sample some of the delicious local seafood.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please consult the "Itinerary" of this stage. Enjoy your journey!
Astoria - United States - North America - Road Trip - Wikimedia Commons
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Astoria
[detailsContainer]
Astoria, Oregon is the perfect ending point of the Oregon Trail on US 20 Road Trip. Located at the mouth of the Columbia River, Astoria is the oldest American settlement west of the Rocky Mountains. This charming city is filled with history and culture, sure to make your road trip one to remember.
No trip to Astoria would be complete without a visit to the Astoria Column. This 125-foot monument stands atop Coxcomb Hill, offering breathtaking views of the city and the Columbia River. Be sure to take a stroll along the Astoria Riverwalk, a 1.5-mile path that follows the river and connects Astoria’s bustling downtown district to the waterfront.
If you’re an outdoor enthusiast, you’ll love the nearby Fort Stevens State Park. This 4,300-acre park offers a variety of outdoor activities, such as camping, biking, fishing, and exploring the historic fort. You can even visit the wreck of the Peter Iredale, a steel-hulled sailing ship that ran aground in 1906.
Those traveling by air can fly into Portland International Airport (PDX), located about 80 miles away. Once you’ve arrived, you can rent a car and make the two-hour drive to Astoria. With its stunning views and abundance of outdoor activities, Astoria is the perfect place to end your Oregon Trail on US 20 Road Trip.
Oregon Trail on US 20 Road Trip at a glance
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Start:
Boston
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End:
Astoria
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Distance:
5,426 km
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Stay:
21 days
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Getting there:
Logan International Airport (BOS)
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When to drive:
May, June, July, August, September
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More info:
More info you can find in the "Itinerary" section at each stage.
Before you set off
The US Route 20 Road Trip is an epic cross-country adventure spanning approximately 5,415 kilometers (3,365 miles) from the historical city of Boston, Massachusetts, to the picturesque coastal town of Newport, Oregon. This route, known as the longest Road in America, provides travelers with an extraordinary opportunity to witness the rich tapestry of American scenery, culture, and history. Along this expansive journey, Roadtrippers will encounter charming small towns, bustling cities, and stunning natural sites that together paint a comprehensive portrait of the United States.
Key Destinations and Top Sights:
- Starting in Boston, delve into American history by walking the Freedom Trail and visiting iconic landmarks such as Faneuil Hall and the USS Constitution.
- In Albany, New York's capital, marvel at the grandeur of the Empire State Plaza and the stunning architecture of the State Capitol.
- Experience the awe of Niagara Falls near Buffalo, and don't miss out on the local culinary delight of Buffalo wings in their birthplace.
- Chicago, known as the Windy City, offers a skyline punctuated by architectural masterpieces like the Willis (Sears) Tower and cultural hotspots such as The Art Institute of Chicago.
- Sioux City, Iowa, provides insights into the region's pioneer past and the explorations of Lewis and Clark at the dedicated Interpretive Center.
- Casper, Wyoming, serves as a gateway to the rugged beauty of the West with nearby destinations like Casper Mountain and the National Historic Trails Interpretive Center, which recounts the journeys of early settlers and Native American history.
Best Time to Go:
Summer is the prime time for the US Route 20 Road Trip, typically from late May to early September, when the weather is most favorable for travel. During these months, the Roads are generally clear of snow, and the longer daylight hours allow for more sightseeing opportunities.
Potential Risks:
Travelers should prepare for a range of driving conditions, including mountain passes, rural Roads, and busy urban streets. Weather can vary dramatically across different regions, so pack accordingly for potential rain, heat, or cold snaps. Be mindful of wildlife on rural highways and remain vigilant for areas with limited services, especially in the more remote stretches of the West.
Interesting Facts for Roadtrippers:
- US Route 20 is rich in historical significance, intersecting with the Oregon Trail, the Pony Express route, and touching upon sites of Native American importance.
- A comprehensive 21-day itinerary allows for an immersive experience without feeling hurried, with time allocated for both planned attractions and spontaneous discoveries.
- This journey is a testament to the variety of driving experiences available in the US, from the densely populated East Coast to the open landscapes of the American West.
- The Road Trip's affordability and accessibility make it an appealing choice for travelers seeking an extensive exploration of the US on a modest budget.
A good choice for:
The US Route 20 Road Trip is more than just a means of travel; it's a pathway to the heart of America, offering endless opportunities for adventure, education, and personal growth. With strategic planning and a sense of adventure, this cross-country quest is poised to become an unforgettable expedition in the life of any intrepid traveler.
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