North West Cowboy Tour

19 days
Difficulty Level
6360 km

North West Cowboy Tour

The Northwest “Cowboy Tour” offers a thrilling adventure through America’s Great Northwest, beginning in Los Angeles and concluding in Chicago. Riders will traverse the legendary Pacific Coast Highway 1, recognized as the fifth-best motorcycle road in the country, the remote stretches of “The Loneliest Road in America” (US 50), and the iconic Beartooth Highway, which is acclaimed as the top motorcycle road in the US.

The tour is not just about the ride; it’s a comprehensive exploration of spectacular landscapes and fascinating attractions. Starting from the bustling streets of Los Angeles, participants will ride through the charming “Danish” town of Solvang, experience the iconic cityscape of San Francisco, and step back in time in Virginia City. The journey continues through the natural wonders of Yellowstone National Park, with its famous Old Faithful Geyser, and the historical Buffalo Bill’s Cody. The Black Hills of South Dakota offer a unique riding experience, with visits to Sturgis, home of the legendary motorcycle rally, Mount Rushmore, and the Crazy Horse Memorial. The Custer National Park and its Wildlife Loop provide an opportunity to see wild buffalo in their natural habitat, while the Badlands present a starkly beautiful landscape.


Motorcycle/Car rental w/unlimited milage
1st choice vehicle model class
Shared room in biker-friendly hotels
Continental breakfast at most hotels
Entrance fees Nat. parks
Welcome meeting
Multi-lingual Tour leader
Transport to rental company
Support van w/ luggage
State min. SLI insurance
Loss damage Waiver
Half-shell helmet
Tour PDF w/route description.
Pictures from the tour
NOT Included
Optional attractions
Vehicle model guarantee
Security deposit for LDW
Food and beverages
LDW Zero & insurance upgrades
Anything not listed in “Included” above



Day 1: Departure - Arrival Los Angeles, California

Welcome to Los Angeles!

The start of the Northwest “Cowboy Tour” sets the tone for the entire adventure. Upon the arrival of all tour participants, the group convenes for a warm welcome greeting and refreshments, providing an excellent opportunity for introductions and initial bonding.

The evening’s agenda is focused on getting to know each other, an essential aspect of group tours, especially one as intimate and experiential as a motorcycle journey across the United States. Eating dinner together in true American style not only offers a taste of the country’s diverse culinary traditions but also serves as a communal activity that fosters group cohesion.


Day 2: Los Angeles - Solvang

(Driving day 1: 215 km/134 miles)

The kickoff of the Northwest “Cowboy Tour” is meticulously planned to ensure participants are well-informed and prepared for the journey ahead. The day begins with an informational meeting that covers all aspects of the tour. This meeting also addresses practical information and preparations related to motorcycle rentals, ensuring that every participant is ready and equipped for the start of their adventure.

After checking out of the hotel, the group officially embarks on their Cowboy adventure, leaving Los Angeles behind as they head towards the iconic Pacific Coast Highway 1. The ride out of Los Angeles sets the stage for an extraordinary driving experience along one of the most celebrated motorcycle roads in the world.

The route includes a stop at the famous Neptune’s Net, a popular biker restaurant in Malibu, for lunch. This provides a taste of the local biker culture and an opportunity for participants to mingle and share experiences. The journey then continues to Santa Barbara and Stearns Pier, often likened to America’s Riviera due to its similar Mediterranean climate and coastal beauty, paralleling the famed French and Italian Rivieras.

The day concludes in the charming “Danish” town of Solvang, a sister city to Aarhus in Denmark, known for its Danish architectural style and heritage.

This segment of the tour encapsulates the essence of the Northwest “Cowboy Tour” — a blend of motorcycle adventure, cultural exploration, and the joy of discovering new landscapes and communities, all while enjoying the camaraderie of fellow motorcycle enthusiasts.


Day 3: Solvang - Monterey

(Driving day 2: 339 km/210 miles)

Leaving the Danish charms of Solvang behind, the Northwest “Cowboy Tour” journey continues towards the southern reaches of California. As you ride along the Pacific Coast Highway 1, the experience becomes increasingly mesmerizing. The journey past Big Sur is a highlight of the tour, where participants can bask in the warm California sun and enjoy the refreshing salty sea air. The Pacific Coast Highway 1, particularly through Big Sur, offers miles of stunning views where the Santa Lucia Mountains dramatically meet the Pacific Ocean.

As the day progresses, the tour reaches Monterey, a destination known for its historical significance and natural beauty. Monterey is also celebrated for the Laguna Seca Raceway, a venue that hosts major automobile and motorcycle racing events, drawing motorsports enthusiasts from around the globe.

The afternoon and evening in Monterey offer a change of pace, with time to explore Cannery Row. This waterfront street, once the center of the sardine packing industry, is now lined with inviting hotels, shops, and restaurants, offering a glimpse into Monterey’s rich history and vibrant contemporary culture. The day concludes with dinner at Fisherman’s Wharf, another iconic Monterey landmark known for its seafood restaurants, stunning ocean views, and lively atmosphere.


Day 4: Monterey - San Francisco

(Driving day 3: 192 km/119 miles)

Continuing the Northwest “Cowboy Tour,” the next leg takes you through the majestic Big Basin Redwood State Park, renowned for its ancient coastal redwoods. The park’s curvy and narrow motorcycle roads offer an exhilarating riding experience that’s sure to leave an indelible mark on your memory. Riding amidst the towering redwoods, some of the tallest and oldest trees on Earth, is an awe-inspiring experience.

A stop for lunch at “Alice’s,” a famous biker bar, adds a layer of authentic local motorcycle culture to your journey. It’s places like Alice’s that capture the essence of the motorcycle touring community, offering great food, camaraderie, and a shared appreciation for the open road.

Arriving in San Francisco, the tour takes a more urban turn. Staying near the city center, participants have the opportunity to explore one of America’s most unique and vibrant cities. San Francisco’s blend of individualism, liberal spirit, and European flair makes it a fascinating destination.

Exploring San Francisco, participants are encouraged to visit iconic locations like Fisherman’s Wharf, known for its seafood, bustling atmosphere, and panoramic views of the bay. The city’s famous cable cars offer a nostalgic way to navigate its hilly streets, providing not just a mode of transport but a journey through San Francisco’s historic heart.

For those interested in delving deeper into the city’s attractions, Alcatraz Island presents a captivating glimpse into history as a former federal prison now serving as a public museum. Additionally, harbor cruises provide a unique perspective of the city from the water, while a visit to Chinatown offers a taste of the city’s diverse cultural fabric. Lombard Street, with its distinctive hairpin turns, and the scenic beauty of the San Francisco Bay Area, further highlight the city’s eclectic charm.


Day 5: San Francisco - Virginia City

(Driving day 4: 428 km/266 miles)

Departing from San Francisco, the Northwest “Cowboy Tour” takes an iconic turn as participants ride across the world-famous Golden Gate Bridge. This moment is a highlight of the tour, providing an opportunity to pause and appreciate the majestic views of the bridge with the backdrop of San Francisco.

The journey continues northward to Sacramento, the capital city of California, marking the beginning of an entirely different phase of the adventure on “The Loneliest Highway in America” (Highway 50). This route is famed for its expansive landscapes and the sense of solitude it offers, contrasting sharply with the bustling urban environment left behind in San Francisco.

Driving along the shores of Lake Tahoe integrates natural beauty with the thrill of the ride. Lake Tahoe, renowned for its clear, cobalt-blue waters and the picturesque mountains that surround it, is a popular vacation spot both in summer and winter.

The day’s ride concludes in Virginia City, a town that transports visitors back to the days of the Old West. Known for its rich history tied to the 19th-century mining boom, Virginia City offers a unique blend of historic charm and fun, with its well-preserved buildings, museums, and antique shops. This historic town provides an immersive experience into the past, allowing riders to explore its legacies of silver mining and the vibrant culture that emerged during the boom times.


Day 6: Virginia - City - Ely

(Driving day 5: 499 km/310 miles)

Riding on “The Loneliest Highway in America” (Highway 50) offers a day of exploration through the vast, open landscapes that define this stretch of road. A notable stop on this leg of the tour is the famous Shoetree near Middlegate. The Shoetree has become a curious landmark, adorned with shoes that travelers have left hanging from its branches over the years. The tradition and the story behind the Shoetree make it a fascinating point of interest, adding a touch of whimsy and human connection to the otherwise desolate route. It serves as a reminder of the countless travelers who have passed this way, each contributing to the story of Highway 50 in their unique way.

Continuing the ride to Eureka, the tour experiences the raw beauty of Highway 50 to its fullest. Eureka, where the night is spent, is another example of the small, historic towns that dot this lonely route. Known for its preservation of 19th-century architecture and as a remnant of Nevada’s rich mining history, Eureka offers a glimpse into the past and a quiet respite after a day of riding through the vastness of the Nevada landscape.


Day 7: Ely - West Wendover

(Driving day 6: 225 km/140 miles)

Today marks the culmination of our journey on Highway 50 as we pivot northward, setting our sights on the majestic Yellowstone National Park. Our route not only continues along this iconic stretch but also intersects with another renowned pathway, “The Lincoln Highway” (US 93).

Upon reaching West Wendover, our day takes an exhilarating turn with a visit to the legendary Bonneville Salt Flats International Speedway. This vast expanse of salt crust on the western edge of the Great Salt Lake Desert is renowned as a mecca for speed enthusiasts, holding numerous land speed records and serving as a dramatic backdrop for various films. It’s a place where the spirit of adventure meets the pursuit of speed, encapsulated by the playful challenge: “Harley owners, do your best…”


Day 8: West Wendover - Garden City

(Driving day 7: 384 km/240 miles)

Today’s journey begins with a necessary stretch on I-80, known as the “transport leg” of our route. While it may not offer the scenic allure or the thrilling curves of more remote highways, it serves as the most efficient path towards our next adventure. This segment is a reminder that every journey includes moments of transition, setting the stage for the excitement that lies ahead.

As we veer north onto Highway 89, the day’s ride takes a dramatic turn for the better. This route leads us towards Garden City, nestled by the stunning Bear Lake, and promises an engaging ride through captivating mountain roads. The transition from the straightforward passage of I-80 to the winding, elevation-changing paths of Highway 89 highlights the diverse experiences that motorcycle touring offers.

The journey to Garden City is not just about reaching our destination but enjoying the exhilarating mountain roads that challenge and delight. With each turn and ascent, riders will encounter breathtaking vistas and the pure joy of navigating through the natural beauty of this region.


Day 9: Garden City - Jackson

(Driving day 8: 234 km/146 miles)

Today, our adventure takes us closer to the enchanting landscapes of Yellowstone National Park and through the exhilarating “Wild West Run.” Departing northward, we first encounter the serene beauty of Bear Lake. Bear Lake, often referred to as the Caribbean of the Rockies for its intense turquoise-blue water, offers a picturesque start to the day.

Our journey continues to Montpelier, diving deeper into the lore of the American West with a visit to the historic site of Butch Cassidy’s infamous bank robbery. This stop offers a tangible connection to the Wild West’s storied past, bringing history to life and enriching our understanding of the American frontier.

The route from Montpelier to Jackson unfolds along fun, twisty roads that promise an engaging ride through the heart of the scenic landscapes. Jackson, nestled in the valley of Jackson Hole, is known as a luxurious retreat for those escaping the bustle of city life, particularly attracting vacationers from California seeking tranquility and natural beauty.

The day culminates at the famous Million Dollar Cowboy Bar in Jackson. This iconic establishment, with its unique Western decor, saddle bar stools, and live country music, offers the perfect backdrop to reflect on the day’s journey and mingle with fellow adventurers. It’s an evening spent in the spirit of the Old West, celebrating the day’s discoveries and the shared experiences of the road.


Day 10: Jackson - Cody

(Driving day 9: 379 km/237 miles)

Today heralds a truly magnificent chapter of our journey, as we delve into the heart of Grand Teton and Yellowstone National Park, embarking on the renowned Wild West Run motorcycle route. This path, stretching from Jackson to Yellowstone Lake, is celebrated as one of the United States’ most beloved motorcycle routes, offering riders unparalleled natural beauty and a sense of adventure that’s deeply rooted in the American wilderness spirit.

Our journey begins with the majestic views of Jackson Lake, setting the stage for the natural wonders that await. As we progress, the highlight of our day emerges with a visit to the iconic Old Faithful Geyser. Old Faithful stands as a testament to nature’s punctuality, with its eruptions occurring at intervals ranging from 35 to 120 minutes. This natural marvel, named during the Washburn-Langford-Doane Expedition in 1870, was the first geyser in Yellowstone to be named, symbolizing the park’s rich history and the exploration spirit of the 19th century.

Venturing further into Yellowstone, we take the Grand Loop Road, leading us to the breathtaking vista of Artist Point. This spot offers a panoramic view of the Lower Falls of the Yellowstone River, encapsulating the sublime beauty that defines Yellowstone National Park. Our adventure continues as we encounter live buffalo herds, offering an up-close experience with these majestic animals. While these encounters promise thrilling moments, we remain cautious of the wildlife, including bears, wolves, elk, and buffalos, respecting their natural habitat and maintaining a safe distance.

Our day concludes in Cody, the home turf of the legendary Buffalo Bill (William F. Cody), where the spirit of the Old West is palpable. Dining at the historic Irma Hotel, named after Buffalo Bill’s daughter and opened in 1902, we’re immersed in the legacy of one of the most iconic figures of the American West.


Day 11: Cody - Beartooth Hwy - Cody

(Driving day 10: 364 km/227 miles)

Today’s journey is set to be an unforgettable highlight for many, as we take on the world-renowned “Beartooth Highway,” acclaimed as the number one motorcycle route in the United States. The fame of Beartooth Highway among bikers globally is well-earned, thanks to its unparalleled winding mountain roads that ascend and descend the mountain, featuring tight hairpin turns and breathtaking views. This segment of the tour represents not only the pinnacle of motorcycle touring but also its most challenging driving leg. As such, we will proceed at a comfortable and safe pace, ensuring that everyone can navigate the road securely while fully immersing themselves in the experience and the stunning landscapes.

But the adventure doesn’t end there. Before reaching Beartooth Pass, we will traverse the Chief Joseph Scenic Byway, another journey that promises to be a lifetime experience in its own right.

After our thrilling ride to Beartooth Pass and back, we return to Cody, where you have the chance to visit the spectacular Buffalo Bill Center of the West. This museum complex is dedicated to preserving the legacy of Buffalo Bill Cody and the history of the American West, offering an in-depth look at the natural and cultural history of the region.


Day 12: Cody - Gillette

(Driving day 11: 408 km/255 miles)

Embarking on another day filled with the allure of the open road, we delve deeper into the heart of the American landscape, navigating through the spectacular curves and thrilling mountain roads that lead us into Big Horn Canyon & National Forest. This part of our journey is characterized by its breathtaking scenery, where every turn reveals another awe-inspiring view, ensuring that your smile remains a constant companion throughout the ride.

The Big Horn region is renowned for its rugged beauty, encompassing vast canyons, lush forests, and an abundance of wildlife, offering a backdrop that enhances the thrill of the ride with its natural splendor.

Our journey today includes a delightful pause for lunch and some cowboy-shopping in Sheridan. This charming town, known for its rich history and Western culture, provides a perfect setting to stretch your legs, explore local shops, and perhaps take home a piece of the Wild West.

Continuing our adventure, we ride past the iconic “Spotted Horse” bar on our way to Gillette, where we will rest and recharge for the next day.


Day 13: Gillette - Deadwood

(Driving day 12: 257 km/160 miles)

Today, our journey takes us into the heart of the Black Hills, an area renowned not only for its stunning natural beauty but also as the site of the Sturgis Motorcycle Rally, the epitome of motorcycle culture and camaraderie. This leg of the tour promises an unforgettable adventure through landscapes and history that have captivated the imagination of riders and adventurers worldwide.

Our adventure begins with a ride to the iconic Devil’s Tower, an awe-inspiring geological feature that rises dramatically from the rolling hills of northeastern Wyoming. This national monument, known for its towering presence and as a sacred site to many Native American tribes, gained additional fame as the backdrop for the classic sci-fi movie “Close Encounters of the Third Kind.”

Continuing our journey, we make our next stop in Sundance, a town immortalized by one of its most infamous visitors, the Sundance Kid. This historic town offers a glimpse into the Wild West era that defines much of American folklore.

Our path then leads us through the breathtaking Spearfish Canyon, a natural masterpiece with towering limestone cliffs, cascading waterfalls, and a vibrant array of flora and fauna. Riding through Spearfish Canyon is like moving through a living painting, an experience where the beauty of nature envelops you at every turn.

The day’s journey also takes us through Deadwood, a town that has preserved its 19th-century charm and notorious past. A visit to the No. 10 Saloon is a journey back in time, standing in the very spot where Wild Bill Hickok met his fate while holding what is now famously known as the “Deadman’s Hand.” This moment in history adds a tangible connection to the legends and tales of the Old West that have shaped America’s cultural heritage.


Day 14: Deadwood - Black Hills Run - Sturgis

(Driving day 13: 275 km/172 miles)

Today’s expedition immerses us in the heart of the Black Hills, offering a comprehensive exploration of its most famed attractions. Our journey through the Black Hills Run showcases the diverse beauty and rich history of this region, leading us to the monumental Crazy Horse Memorial. This colossal rock carving, still in progress, stands as a tribute to the Native American warrior, Crazy Horse, and represents the world’s largest mountain carving.

Continuing our adventure, we venture to Custer and the encompassing Custer State Park, a region that captivated General George A. Custer with its stunning landscapes and abundant wildlife. The park’s beauty is on full display as we navigate the Needles Highway, known for its impressive granite spires and narrow tunnels. The Wildlife Loop within the park offers the possibility of encountering live buffalo, providing an up-close experience with these majestic creatures in their natural habitat.

Lunch in Custer State Park offers a moment to relax and enjoy the natural surroundings before we proceed to the iconic Mount Rushmore National Memorial. Here, we witness the colossal visages of Presidents George Washington, Thomas Jefferson, Theodore Roosevelt, and Abraham Lincoln carved into the granite face of Mount Rushmore.

Our journey through the Black Hills culminates with a ride on the famous Iron Mountain Road, known for its pigtail bridges and stunning vistas, offering a unique driving experience.

The day’s adventures lead us to Sturgis, the epicenter of the Sturgis Motorcycle Rally. This small town transforms annually into a hub of motorcycle culture, drawing enthusiasts from around the globe. Our visit to the world-famous Knuckle Saloon caps off the day with a foray into biker culture, offering an opportunity to celebrate our journey in true biker style.


Day 15: Sturgis - Oacoma

(Driving day 14: 424 km/264 miles)

As we bid farewell to Sturgis, our journey shifts eastward, introducing us to new adventures and iconic American landscapes. Our first destination is the renowned Wall Drug, an emblematic roadside attraction that started as a small drug store offering free ice water to travelers in the 1930s and has since evolved into a sprawling complex of shopping, dining, and entertainment. It’s a place where the charm and spirit of the Old West come alive, offering our last chance to “cowboy up” with its array of Western memorabilia, unique gifts, and quirky attractions.

From there, we venture into the stark and stunning expanse of Badlands National Park. The park’s rugged beauty is unlike any other, with its striking geological formations and layered rock deposits that form a natural canvas of vibrant colors. The Badlands are not only a marvel of nature’s artistry but also a paleontological treasure trove, containing fossils that tell the story of ancient mammals such as rhinoceroses, horses, and saber-toothed cats that once roamed this land. Today, the park’s 244,000 acres are a vibrant ecosystem home to bison, bighorn sheep, prairie dogs, and the elusive black-footed ferret.

The journey continues as we enter the territory of the Cheyenne Indian, a land immortalized by the film “Dances with Wolves.” This beautiful expanse, with its rolling hills and wide-open skies, provides a profound sense of connection to the land and its history. Driving through this territory offers a glimpse into the rich cultural heritage of the Native American tribes that have called this land home for centuries.

Our day concludes in the small town of Oacoma. Nestled along the Missouri River, Oacoma serves as the perfect backdrop for the night, offering tranquility and comfort as we prepare for the next leg of our adventure.


Day 16: Oacoma - Worthington

(Driving day 15: 334 km/209 miles)

Today’s journey takes us through the heart of America’s farm country, an expanse of fertile lands dotted with endless cornfields. This region holds a rich history of Scandinavian immigration, where settlers from Norway, Sweden, Denmark, and Finland left their mark on the landscape and culture of the Midwest. It’s a drive that connects us not only with the agricultural backbone of America but also with the diverse heritage that shapes this country.

Our first stop is a unique and whimsical landmark, “The World’s Only Corn Palace” in Mitchell, South Dakota. This one-of-a-kind structure is a testament to the region’s agricultural pride, adorned with murals and designs made entirely from naturally colored corn and other grains. The Corn Palace serves as a multi-purpose arena hosting events and concerts, but more importantly, it stands as a living museum of agricultural artistry, celebrating the area’s farming heritage.

Continuing our exploration, we visit the Porter Sculpture Park, home to the imposing 60 Foot Bull Head Sculpture among many other striking metal artworks. Created by artist Wayne Porter, this outdoor gallery transforms the rolling prairie into a canvas for imaginative and larger-than-life sculptures. The park’s whimsical and thought-provoking pieces offer a stark contrast to the natural and cultivated landscapes that surround us, highlighting the creative spirit that thrives in this region.

Our drive then leads us to Sioux Falls for a late lunch, offering a chance to experience the local cuisine and perhaps catch a glimpse of the city’s namesake waterfalls, a natural beauty that adds to the charm of South Dakota’s largest city.

The day’s journey concludes in Worthington, Minnesota, a community that embodies the Midwestern spirit of hospitality and heritage. Nestled in a region known for its agricultural productivity and scenic beauty, Worthington is the perfect place to reflect on the day’s journey through landscapes that are as rich in history and culture as they are in natural beauty.


Day 17: Worthington - Lake City

(Driving day 16: 384 km/240 miles)

For music enthusiasts, today promises to be an unforgettable experience as we pay homage to one of the most iconic figures in the music world. Our journey takes us to Paisley Park, the private estate and production complex of the late, great Prince. Nestled in the quiet suburb of Chanhassen, Minnesota, Paisley Park is more than just a home; it was Prince’s creative sanctuary, where he lived, recorded, and poured his soul into his music. Visiting Paisley Park offers a deeply personal glimpse into the life of this incredibly gifted artist. The complex has been transformed into a museum, showcasing artifacts from Prince’s life.

After immersing ourselves in the legacy of Prince, our journey continues along the scenic Highway 61, following the majestic Mississippi River towards Lake City. This route, often referred to as the “Great River Road,” is famed for its breathtaking views and its significance in the history of American music, particularly the blues genre. The drive to Lake City is a beautiful transition from the urban setting of Minneapolis to the natural beauty that lines the banks of the Mississippi River.


Day 18: Lake City - Chicago

(Driving day 17: 550 km/343miles)

As our North-West Cowboy adventure nears its conclusion, we embark on our final day of riding. The day begins with a continuation of our scenic drive along the Mississippi River.

Following lunch by the river, our journey takes a turn onto the backroads leading to Chicago. This route, less traveled compared to the highways, offers a more intimate farewell to the countryside, winding through small towns and rural landscapes that provide a quiet backdrop for our contemplation of the adventure we’re concluding. These backroads are the final chapters of our story, a story that has taken us through some of the most iconic and breathtaking parts of the American Northwest and beyond.

Upon arrival in Chicago, we will return the bikes, marking the end of our riding journey but not the end of our adventure together. Chicago, with its vibrant culture, towering skyline, and deep-rooted musical heritage, offers a fitting backdrop for our last night together.


Day 19: Departure Chicago - Home Travel

As we say goodbye to the awe-inspiring terrains of the American Northwest and the dynamic buzz of Chicago, our group makes its way to the airport aboard a shuttle, closing the chapter on a remarkable journey.

We sincerely thank you for embarking on this exploration with Explorify. As we go our separate ways, we wish you a safe return home and eagerly anticipate the chance to embark on new adventures together, whether it’s across the US, South America, Asia, Oceania, Africa or along the historical trails of Europe.

Note: For those of our travelers heading back to Europe, it’s worth noting that the time difference means you’ll be arriving home the day after you leave the US, effectively extending your adventure by one more day.

While this program outlines our tour, the unpredictable nature of travel means that there might be some alterations along the way. Our dedication to delivering a comprehensive and rewarding experience drives us to continuously seek ways to enhance our journey, adapt to new situations, and embrace opportunities to expand our itinerary. Although adjustments may be required, they are always aimed at elevating your experience and ensuring the adventure you signed up for is truly memorable. Unexpected program enhancements often lead to delightful surprises.

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North West Cowboy Tour