15 Unforgettable Stops on America’s Longest Road: A Journey of Endless Adventure
Traveling from coast to coast via U.S. Route 20, you will encounter an experience that stands out among all road trips and the surroudings. America’s longest road extends 3,365 miles, beginning in Boston, Massachusetts, and arriving in Newport, Oregon.
The Federal Highway Administration reports that 200,000 adventurers take road trips yearly to discover America’s legendary Route 20. According to travel expert Susan Jacobs, Route 20 stands as America’s premier path, displaying history, natural beauty, and cultural richness. This journey appeals to everyone from adrenaline junkies to history enthusiasts as well as nature enthusiasts. Prepare for adventure because we will uncover 15 unforgettable stops next.
Boston, Massachusetts – Where It All Begins
Your adventure starts in Boston, which marks the beginning point of Route 20. Among America’s oldest cities, Boston presents an enduring history that stretches back to 1630. Walking along the celebrated Freedom Trail allows visitors to visit 16 famous historical locations that thousands traverse annually as they follow its 2.5-mile length.
According to travel writer Mark Thompson, Boston represents an ideal blend of ancient history and modern development. Colonial-era landmarks stand beside towering modern skyscrapers in this area. When your journey leads you to Fenway Park exploration or lobster roll indulgence, Boston provides the best starting point for travel.
Cleveland, Ohio – The Rock & Roll Capital
Music lovers, rejoice! The Rock & Roll Hall of Fame in Cleveland attracts over 500,000 visitors yearly from people who appreciate music history. The hall houses legendary collections of items once owned by Elvis Presley, The Beatles, Madonna, and more.
“Cleveland has an unbeatable music legacy,” says museum curator Emily Jones. “From classic rock legends to new artists, this city celebrates it all.”
Newport, Oregon: A Scenic End to the Journey
Route 20 reaches its destination at the gorgeous Oregon shoreline near Newport. This destination pulls in more than 2 million annual visitors because of its classic lighthouses and lively seafood offerings.
“Newport should be every traveler’s destination to cap off their journey,” recommends seasoned traveler Jake Thompson. You will remember Newport for its rocky seaside along with its fresh seafood specialties. Experience unforgettable ocean breezes during your visit to the Oregon Coast Aquarium
Cleveland, Ohio – The Rock & Roll Capital
Music lovers, rejoice! The Rock & Roll Hall of Fame in Cleveland attracts over 500,000 visitors yearly from people who appreciate music history. The hall houses legendary collections of items once owned by Elvis Presley, The Beatles, Madonna, and more.
“Cleveland has an unbeatable music legacy,” says museum curator Emily Jones. “From classic rock legends to new artists, this city celebrates it all.”
Galena, Illinois – Step Back in Time
Galena maintains an impressive collection of its original 19th-century buildings along the Mississippi River. More than one million visitors travel to this town each year to discover historic landmarks such as the former home of Ulysses S. Grant.
“Galena is a true time capsule,” says historian Anne Parker. “It’s perfect for anyone who loves history and small-town charm.”
Chicago, Illinois – The Windy City’s Marvels
As one of America’s premier cities, Chicago boasts an electrifying skyline that captures attention at all hours. Incredible sights at Manhattan Park and Skydeck on Willis Tower coexist alongside Chicago’s world-famous deep-dish pizza. Over 30 million people visited the city in 2021.
“Chicago is a city of endless possibilities,” says local guide Mike Roberts. “Art, food, music—you name it, we have it.”
Dyersville, Iowa – The Field of Dreams
Dyersville is the center of interest for movie and baseball enthusiasts because it contains the well-known “Field of Dreams” movie location. The famous field upholds its magic by allowing visitors to walk its grounds and witness games now and then.
According to filmmaker Tom Mitchell, the location possesses an enchanting character that touches every person who visits. The MLB brought national attention to Dyersville when it hosted a historic game on the Field of Dreams site in 2021.
Craters of the Moon, Idaho: Otherworldly Beauty
The national monument provides unreal lava terrains alongside rugged landscapes, which draws more than 200,000 visitors annually.
“As a geologist, I would say that walking here reminds me of another planet,” explains Brian Foster. The landscape features from the volcanic region maintain a surprising blend of wonder with ghostly allure. Discover the beauty of Craters of the Moon through descriptive hikes and landscape-spreading drives around its lava tubes.
Bend, Oregon: An Outdoor Paradise
Winding through the Cascade Mountains, Bend offers top-rated hiking and skiing trails and amazing craft breweries.
“You don’t need to look past Bend if you love spending time outdoors,” adventure guide Sarah White points out. Sightseeing at the Deschutes River and mountain biking adventures are infinitely enjoyable.
Omaha, Nebraska – Culinary and Cultural Delights
The Henry Doorly Zoo is among the world’s top attractions, outside of Omaha’s culinary variety. Millions of tourists visit each year to walk through the active and bustling downtown area.
Food critic Linda Waters explains that Omaha provides diners with unexpected combinations of tastes and diverse experiences. Experience Omaha steakhouse classics by sampling their renowned dish and walking through the Old Market district.
Yellowstone National Park, Wyoming: A Natural Wonder
A true highlight of Route 20, Yellowstone welcomes over 4 million visitors each year. Witness geysers, hot springs, and abundant wildlife in America’s first national park.
“Yellowstone is an experience unlike any other,” says park ranger Megan Blake. “It’s nature at its most raw and beautiful.” Explore Old Faithful, the Grand Prismatic Spring, and miles of stunning landscapes.
Cody, Wyoming: The Spirit of the Wild West
Nestled near the eastern entrance of Yellowstone, Cody is a town that embodies the spirit of the Old West. Named after Buffalo Bill Cody, it attracts over 500,000 visitors annually with its rich cowboy culture and thrilling rodeos.
“Cody is the gateway to adventure,” says local historian Jim Matthews. “It’s where the frontier spirit still lives on.” Visit the Buffalo Bill Center of the West, enjoy a night at the famous Cody Nite Rodeo, and take in the stunning mountain scenery
Eugene, Oregon: A Cultural Hub with Natural Beauty
Eugene sustains an active arts and culture landscape through its distributed network of cultural institutions and artistic spaces, which includes many galleries and theaters. Among the city’s extensive cultural repertoire, travelers will find the Hult Center for the Performing Arts and the Jordan Schnitzer Museum of Art.
“Eugene blends nature and culture beautifully,” says art curator Lisa Morgan. Few places offer more scenic trails or vibrant art festivals, making Eugene an essential destination for all visitors.
Sioux City, Iowa: A Historic River Town
“Sioux City offers an incredible blend of history and modern attractions,” says travel guide Michelle Carter. “The Lewis and Clark Interpretive Center gives visitors a deep dive into America’s past.” More than half a million tourists travel through this region each year.
Casper, Wyoming: Gateway to the Rockies
Casper offers extensive cultural activities. The city provides numerous options through its local theaters and art galleries both its residents and their visitors can explore. Emily Johnson, a cultural affairs coordinator, states, “Casper’s cultural scene is a reflection of its rich history and vibrant community spirit.”
Disclaimer – This list is solely the author’s opinion based on research and publicly available information.
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