What an adventure it has been! Our group of eight motorcycles embarked on an unforgettable cross-continent odyssey, transforming thousands of kilometers into a tapestry of incredible memories, stunning landscapes, and legendary roadside encounters. From the heart of North America to the Pacific Coast and back, this trip was the ultimate test of endurance, spirit, and passion for the open road.
Here’s a look back at each remarkable day of our journey:
Day 1: The Great Escape – From Home to the Heartland Gateway
Day 1, wasn’t the start of Route 66, but the vital first leg of getting to our official starting line in Chicago. Our engines roared to life bright and early from our home base in Brampton, Ontario, packed for a long haul. The air was thick with anticipation, the hum of eight machines a prelude to the thousands of kilometers ahead. Our initial target: Windsor, Ontario, a considerable approximately 375 kilometers (233 miles) away, strategically positioning us for the border crossing and the onward push towards Illinois.
Day 2: The Great Escape – From Home to the Heartland Gateway
Our epic journey kicked off from our starting point in Southern Ontario, as we geared up and made our way across the border. The excitement was palpable as we cleared customs at the Ambassador Plaza, officially beginning our American adventure. After a solid day of riding, we settled in at Homer Glen, Illinois, marking our first successful day on the road, covering approximately 400 kilometers (272 miles).
Day 3: Route 66 Beckons – Exploring Missouri’s Quirky Charms
Day 3 saw us truly embrace the spirit of Historic Route 66. Leaving Homer Glen, we dived into the iconic Mother Road, exploring fascinating stops like the mysterious Meramec Caverns and the delightfully bizarre Uranus Fudge Factory. Our day concluded in Sullivan, Missouri, having ridden roughly 400 kilometers (249 miles).
Day 4: The Heart of Route 66 – Legends and Landmarks
From our base near St. Louis, Missouri, Day 4 was a deep dive into Route 66’s classic Americana. We visited the imposing Old Joliet Prison and posed with the famous Gemini Giant in Wilmington. Lunch at the retro Polk-A-Dot Drive-In fueled our ride through Pontiac, past Ambler’s Texaco Station. The day was packed with giants – from Paul Bunyan in Atlanta to the World’s Largest Covered Wagon in Lincoln and the Lauterbach Muffler Man in Springfield. We ended with a spectacular sunset view of the Gateway Arch from the Mississippi River Overlook in East St. Louis, covering around 490 kilometers (304 miles).
Day 5: Pushing West – From Missouri to the Oklahoma Panhandle
Leaving St. Louis behind, Day 5 was a significant mileage day across the vastness. We continued our exploration of Route 66, with quick stops at various local gems and refueling points as we journeyed westward. Our destination for the night was Elk City, Oklahoma, after a substantial ride of approximately 903 kilometers (561 miles).
Day 6: Texas Big Sky – Icons of the Mother Road
Day 6 truly embodied the spirit of the American Southwest. Starting from Elk City, Oklahoma, we continued our Route 66 pilgrimage, eventually rolling into the vast landscapes of Texas. Highlights included the unique architecture of the U-Drop Inn Cafe and the vibrant artistry of Cadillac Ranch. The day’s ride ended in Amarillo, Texas, with a memorable stop at the famous Big Texan Steak Ranch, covering about 600 kilometers (373 miles).
Day 7: Into the Desert – Across Texas and New Mexico
Our journey continued westward from Amarillo, Texas, into new horizons. We encountered more quirky Route 66 landmarks like the Leaning Tower of Texas and Bug Ranch, truly soaking in the unique character of this historic highway. The vast stretches of road led us into New Mexico, where we settled into Holbrook, Arizona, after riding approximately 625 kilometers (388 miles).
Day 8: Painted Deserts and Meteor Strikers – Arizona’s Wonders
From Holbrook, Arizona, Day 8 brought us face-to-face with Arizona’s dramatic geological history. We explored the stunning Painted Desert Visitor Center within Petrified Forest National Park, marveling at the ancient landscapes. A classic stop in Winslow, Arizona, for that iconic photo op, and a visit to the astounding Meteor Crater, rounded out a day of incredible sights. We concluded our day in Gallup, New Mexico, after approximately 285 kilometers (177 miles).
Day 9: New Mexico’s Charms to Arizona’s Grandeur – Approaching the Canyon
Day 9 saw us continue our ride from Gallup, New Mexico, back into Arizona, with our sights set on the ultimate natural wonder. We enjoyed the open roads, passing by intriguing spots and making practical stops as we edged closer to our grand destination. The day’s ride concluded near the Grand Canyon, settling in near Flagstaff and the Cameron Trading Post, covering around 475 kilometers (295 miles).
Day 10: The Grand Canyon Experience – A Day of Awe
This was a full day dedicated to one of the world’s most spectacular natural formations. From our base near Cameron Trading Post, we spent hours exploring the awe-inspiring South Rim of the Grand Canyon, taking in countless vistas from iconic spots like Desert View Watchtower, Lipan Point, Yavapai Point, and Mohave Point. The sheer scale and beauty of the canyon were simply unforgettable. We returned to the Cameron Trading Post area after approximately 374 kilometers (232 miles) of riding and exploring.
Day 11: From Canyon Views to Sin City Lights – Riding to Vegas!
Leaving the profound beauty of the Grand Canyon, Day 11 marked a dramatic shift in scenery and atmosphere. Our journey took us through vast desert landscapes, including a powerful ride past the immense Hoover Dam, before finally arriving in the dazzling oasis of Las Vegas, Nevada. We embraced the vibrant energy of Fremont Street Experience as our main activity, after covering approximately 479 kilometers (298 miles).
Day 12: Pacific Bound – From Nevada Desert to California Coast
Leaving the bright lights of Las Vegas, Day 12 began our westward push towards the Pacific. Our ride took us through the vast Mojave Desert, following segments of historic Route 66, before finally arriving at the iconic Santa Monica Pier in California. The sight of the Pacific Ocean and the lively atmosphere of Pacific Park were a fitting reward after riding approximately 427 kilometers (265 miles).
Day 13: California Dreaming – Coastal Ride to Monterey
From the famous Santa Monica Pier, Day 13 was a stunning ride up the beautiful California coast. We experienced the scenic beauty of El Matador State Beach, enjoyed refreshing breaks at places like Starbucks, and passed by the picturesque Cachuma Lake Recreation Area. The coastal road offered breathtaking views before we arrived at our lodging, the Monterey Hostel, after a journey of approximately 530 kilometers (329 miles).
Day 14: San Francisco Calling – City Sights and a Wharfside Stay!
Day 14 brought us into the iconic hills of San Francisco! Leaving Monterey, we immersed ourselves in the city’s unique charm. We enjoyed panoramic views from Twin Peaks, explored the bustling Fisherman’s Wharf, visited the famous Pier 39 and Ripley’s Believe It or Not!, and savored a meal at The Marine Seafood Restaurant. The day ended with us settling into the San Francisco Fishermen’s Wharf Hotel, having ridden around 179 kilometers (111 miles) around the city.
Day 15: From Golden Gate City to Sapphire Lake – Conquering the Sierra Nevada!
After the vibrant urban exploration of San Francisco, Day 15 brought a dramatic shift in scenery as we aimed for the majestic Sierra Nevada mountains and the legendary Lake Tahoe. We made stops at places like Cafe Franco and Black Bear Diner Vallejo. The highlight was undoubtedly reaching Lake Tahoe, exploring areas like Lake Tahoe Airport, the Beach Retreat & Lodge at Tahoe, and Basecamp on the Pier. Our day concluded with lodging in South Lake Tahoe, after approximately 403 kilometers (250 miles).
Day 16: Conquering the Loneliest Road – Nevada’s Vast Horizons!
Leaving the beauty of Lake Tahoe, Day 16 saw us plunge into the vast, stark landscapes of Nevada, specifically tackling “The Loneliest Road in America” (US-50). We experienced quirky stops like Middlegate Station, explored the intriguing Stokes Castle, and found respite at places like the Owl Club Casino. Our long ride, covering around 465 kilometers (289 miles), ended in Ely, Nevada, at the Prospector Hotel & Gambling Hall.
Day 17: From Nevada Deserts to Utah’s Hidden Gems – Great Basin’s Majesty!
From Ely, Nevada, Day 17 continued our eastward push, bringing us into Utah and a deep dive into the unique natural beauty of Great Basin National Park. We visited the Great Basin Visitor Center and were awestruck by the views from Wheeler Peak Overlook. After a meal at Sugar, Salt & Malt Restaurant, we settled into our lodging in Milford, Utah, having ridden approximately 419 kilometers (260 miles).
Day 18: Red Rock Wonders and Colorful Colorado – Gateway to Arches!
Day 18 brought spectacular transitions from Milford, Utah, to the iconic red rock landscapes and our entry into Colorado. We explored the unique “Hole ‘N The Rock” attraction before immersing ourselves in the stunning beauty of Arches National Park. The day concluded in Grand Junction, Colorado, after approximately 449 kilometers (279 miles), and crossing the Welcome to Colorful Colorado Sign.
Day 19: Ascending the Rockies – From Red Rocks to Mountain Peaks!
Leaving Grand Junction, Colorado, Day 19 was a high-altitude adventure through the heart of the Rocky Mountains. We passed by Teddy Morse’s Grand Junction Harley-Davidson and enjoyed breathtaking views from iconic locations like Vail Ski Resort, Dillon Dam Overlook, and Georgetown Overlook Pull-Out. Our ride, roughly 460 kilometers (286 miles), brought us to Commerce City, Colorado.
Day 20: The Great Plains Marathon – Eastward Bound Across Vast Horizons!
Day 20 was a monumental shift and a true test of endurance – a massive mileage day across the vast American plains. Leaving Commerce City, Colorado, we devoured over a thousand kilometers, crossing into Nebraska at the Welcome to Nebraska Sign and pushing deep into Iowa. This epic ride, approximately 1122 kilometers (697 miles), brought us to Newton, Iowa, at the Best Western Holiday Manor.
Day 21: The Final Frontier – A Marathon to the Motherland!
The grand finale! Day 21 was the longest and most exhilarating day, a true marathon from Newton, Iowa, all the way back to Canada. The iconic World’s Largest Truckstop provided a memorable stop before our triumphant ride across the Ambassador Bridge into Windsor, and the final stretch to our home region in the Huron area. After an incredible 1230 kilometers (764 miles), we were finally home, concluding an epic cross-continent journey!
This trip was more than just miles; it was a journey of discovery, challenge, and unforgettable moments, proving that on two wheels, the adventure never truly ends.