When you set out on U.S. Route 20, you’re driving the longest road in America — stretching an incredible 3,365 miles across the country. Beginning on the Atlantic coast in Massachusetts and ending at the Pacific Ocean in Oregon, this route weaves through 12 different states and takes you past small towns, bustling cities, national parks, and wide-open landscapes.
So if you’re ready for the ultimate cross-country adventure, here are some of the top stops along U.S. Route 20 that highlight its diversity and charm.
Boston, Massachusetts
Boston, where history meets modern charm, serves as a gateway to this epic journey. Known for its pivotal role in American history, Boston’s cobblestone streets and iconic landmarks such as the Freedom Trail offer a glimpse into the past. Imagine strolling through the autumn-kissed streets, taking in the rich cultural tapestry that defines this vibrant city. A visit to the bustling Quincy Market provides a taste of local flavors and energy. Begin your road trip here and feel the pulse of a city that has shaped the nation.
Albany, New York
Nestled along the Hudson River, Albany is a charming blend of old-world elegance and contemporary life. The Empire State Plaza stands as a testament to architectural grandeur, offering panoramic views of the city. As the sun rises, Albany’s skyline is bathed in a golden hue, creating a picturesque start to your day. Historical sites such as the New York State Capitol invite exploration, while the vibrant arts scene adds a modern twist. Albany serves as a delightful contrast to the urban hustle, offering serenity and style.
Cleveland, Ohio
Cleveland, a city with a rock and roll heart, pulses with energy and diversity. The iconic Rock and Roll Hall of Fame stands proudly on the shores of Lake Erie, celebrating music legends and their stories. As you wander downtown, the blend of modern architecture and historic buildings tells a tale of reinvention. The city’s rich cultural scene, from theater to art galleries, offers endless exploration. Cleveland’s unique character makes it a must-stop on this highway adventure, blending creativity with Midwestern warmth.
Chicago, Illinois
In Chicago, architectural wonders meet natural beauty along the shores of Lake Michigan. The towering Willis Tower offers breathtaking views of the cityscape, while the bustling Magnificent Mile invites shopping and dining indulgence. As the day ends, the city transforms into a vibrant tapestry of lights against the night sky. Chicago’s deep-dish pizza and jazz clubs provide a sensory feast, embodying the city’s lively spirit. This metropolis combines urban excitement with cultural richness, leaving a lasting impression on any traveler.
Sioux City, Iowa
Sioux City, a blend of history and innovation, offers a unique stop on this cross-country highway. The historic Fourth Street district, with its preserved architecture, tells stories of bygone eras. As you explore, modern art installations surprise and delight, showcasing the city’s creative spirit. The riverfront provides a peaceful escape, perfect for a leisurely stroll or a moment of reflection. Sioux City’s charm lies in its harmonious blend of past and present, making it a memorable highlight of your journey.
Casper, Wyoming
Casper is where the wild frontier spirit thrives amidst breathtaking natural beauty. Nestled against the backdrop of Casper Mountain, the city offers stunning vistas and outdoor adventures. The National Historic Trails Interpretive Center provides an insightful look into the pioneering past. As you traverse the city, the vast open sky creates a sense of freedom and possibility. Casper is a haven for those seeking both adventure and tranquility, embodying the rugged charm of the American West.
Yellowstone National Park, Wyoming
Yellowstone, nature’s masterpiece, captivates with its geothermal wonders and diverse wildlife. The park’s iconic geysers, such as Old Faithful, erupt with precision, showcasing Earth’s raw power. Vibrant hot springs paint the landscape in surreal colors, while the roaming bison and elk add to the park’s allure. Each corner of Yellowstone reveals a new marvel, offering endless exploration opportunities. This natural paradise is an essential stop, inviting travelers to witness the majestic beauty of the nation’s first national park.
Boise, Idaho
Boise, a vibrant blend of urban and outdoor experiences, welcomes travelers with open arms. The city’s lively downtown offers a mix of independent boutiques, cafes, and cultural venues. The Boise River Greenbelt provides a scenic pathway for walking and biking, showcasing the city’s commitment to nature. Springtime in Boise sees the foothills bloom, painting the landscape with colorful wildflowers. The friendly atmosphere and abundant activities make Boise a delightful stop on this cross-country journey.
Bend, Oregon
Bend, where craft beer flows and outdoor adventures await, is a playground for enthusiasts. The city’s downtown, dotted with breweries, offers a taste of local flavors and innovation. Beyond the city, the Cascade Mountains beckon with trails and breathtaking landscapes. Whether you’re hiking, biking, or simply enjoying a leisurely day, Bend provides the perfect blend of excitement and relaxation. This Oregon gem is a haven for those seeking both thrill and tranquility, set against a stunning natural backdrop.
Newport, Oregon
Newport, where the Pacific Ocean meets rugged cliffs, offers a picturesque end to this journey. The iconic Yaquina Bay Bridge frames the coastal scenery, inviting exploration of the charming harbor and its maritime history. As waves crash against the shore, the scent of saltwater fills the air—a reminder of nature’s power. Newport’s vibrant arts community and seafood delicacies add to its coastal allure. This final stop encapsulates the diverse beauty and cultural richness experienced along this remarkable highway.