Route 66 Motorcycle Group Tour
Guided 14-night Harley-Davidson® adventure cruising historic Route 66 from Chicago to Santa Monica.
There’s no more thrilling way to experience America’s “Main Street” than from the saddle of a Harley-Davidson® motorcycle. This legendary 14-night guided group adventure takes you across nine states from Chicago to Los Angeles, tracing the original Route 66 past neon motels, desert horizons, frontier towns and iconic Americana. With an experienced tour guide leading the ride and a support vehicle following behind, you’ll explore the very best of the Mother Road — including the Cadillac Ranch, the Wigwam Motel, the Route 66 midpoint in Adrian, and the wide-open highways that inspired a century of road-trip storytelling.
Along the way, you’ll stay in hand-picked hotels, enjoy breakfast on riding days, and take unforgettable side trips including a Grand Canyon helicopter experience. Two free days in Santa Fe and Las Vegas add time to relax, explore and share stories with your fellow riders. From the first engine rev in Chicago to the emotional finish at Santa Monica Pier, this is Route 66 exactly as it should be: adventurous, authentic and driven by the unbreakable camaraderie of the open road.
Our prices include optional insurances
Tours run on selected dates April - October
Single rider or Rider + Pillion options
14 night motorbike group tour from £4,984pp including flights
Highlights
Ride a Harley-Davidson® the full length of Route 66 from Chicago to Santa Monica with an expert group guide and support vehicle.
Cruise in style on a late-model Harley-Davidson with a full support team, professional guide and luggage vehicle.
Enjoy a Grand Canyon helicopter tour, National Park entrance fees, breakfast on riding days, and welcome and farewell dinners included.
Celebrate your achievement under the “End of the Trail” sign on Santa Monica Pier before exploring glittering Los Angeles.
Your itinerary
Day 1: Chicago
Welcome dinner, skyline views and the birthplace of blues
Arrive in Chicago, a city famed for its glittering Lake Michigan skyline, deep-dish pizza and world-class blues clubs. After settling in, you’ll meet your guides and fellow riders at a Welcome Dinner — the perfect chance to get to know your group and feel the excitement build. Explore Navy Pier, Millennium Park or the Chicago Riverwalk if time allows before resting up for the first miles of Route 66 tomorrow.
If you are able, we highly recommend an extra night in Chicago prior to your tour to give you time to settle in and explore before starting your tour.
1 Night in
Chicago, IL
Arrival
Day
Day 2: Springfield, Illinois
Begin your Route 66 adventure through Illinois to Springfield, land of Abraham Lincoln.
This morning you’ll transfer to the rental depot, pick up your Harley-Davidson® and get familiar with the bike before rolling out of Chicago on the legendary Pontiac Trail, an early alignment of Route 66. As you ride south, the cityscape gives way to open farmland, roadside diners and classic gas stations. Highlights include Joliet and Wilmington’s towering “Gemini Giant” Muffler Man, a favourite photo stop for Route 66 motorcyclists. Further on, Pontiac’s excellent Route 66 Hall of Fame & Museum and colourful wall murals capture the spirit of the Mother Road. By late afternoon you arrive in Springfield, Illinois’ capital, where Abraham Lincoln once lived and worked — a fitting first stop on your cross-country adventure.
1 Night in
Springfield, IL
200 miles
Day 3: St Louis, Missouri
Two-lane roads, the Mississippi River and the Gateway Arch
Today you cruise through rural Illinois on original two-lane stretches of Route 66, flanked by cornfields, vintage barns and classic roadside signs. Stop in Litchfield for a coffee at the historic Ariston Café, believed to be one of the oldest restaurants on Route 66, and perhaps detour along a preserved section of brick-paved highway near Auburn. As the skyline grows on the horizon, you’ll cross the Mississippi River into Missouri and the vibrant city of St Louis. Here, the 630-foot Gateway Arch towers above the riverfront, symbolising the “Gateway to the West.” You may have time for a tram ride to the top or to explore the riverfront before dinner — perhaps with some famous St Louis-style barbecue and a side of live blues.
1 Night in
St Louis, MO
100 miles
Day 4: Joplin, Missouri
Ozark hills, Devil’s Elbow curves and classic Americana
Leaving St Louis, you quickly trade city streets for the rolling hills and forests of the Missouri Ozarks. This is one of the most enjoyable riding days, with sweeping bends, old-style diners and time-capsule motels along the way. You’ll ride parts of historic Route 66 near places like Lebanon and Devil’s Elbow, where the highway crosses a dramatic bend of the Big Piney River on a classic steel truss bridge. Photo stops might include vintage gas stations and quirky roadside attractions that hark back to the heyday of 1950s motoring. By evening you roll into Joplin, once a booming mining town and now a friendly Route 66 community with murals, cafés and a proud Mother Road heritage.
1 Night in
Joplin, MO
335 miles
Day 5: Oklahoma City, Oklahoma
Cross three states in one day and arrive in the heart of 66
Today you tick off Missouri, Kansas and Oklahoma in a single ride. The Kansas portion of Route 66 may be short, but it packs a punch: tiny Galena with its restored Kan-O-Tex gas station, Baxter Springs’ historic main street, and the famous Rainbow Bridge add real character to this stretch. Crossing into Oklahoma — often called the “heart and soul” of Route 66 — you’ll notice wide skies, rolling prairies and an easy riding rhythm. Stops might include quirky shops, classic diners and historic bridges as you head toward Oklahoma City. Your hotel is close to the lively Bricktown Entertainment District, where former warehouses now house restaurants, bars, live music and a canal-side walkway — perfect for unwinding after a big day in the saddle.
1 Night in
Oklahoma City, OK
255 miles
Day 6: Amarillo, Texas
Chisholm Trail history and Texas-sized hospitality
This morning you ride some of the oldest continuously used stretches of Route 66 in Oklahoma, passing through towns like El Reno and Weatherford with their vintage neon and grain elevators. A visit to one of the local Route 66 museums, such as the excellent one in Clinton, is often included to give you deeper insight into the road’s history and the people who travelled it. Crossing into Texas, the landscape opens up into the vast Panhandle with its big skies and distant horizons. Your day ends in Amarillo, where you’ll experience true Texan hospitality — perhaps at the famous Big Texan Steak Ranch, known for its larger-than-life décor, live music and its (optional!) 72-oz steak challenge.
1 Night in
Amarillo, TX
265 miles
Days 7–8: Santa Fe, New Mexico
Cadillac Ranch, the Route 66 midpoint and Southwest culture
Your day begins at Cadillac Ranch, where ten graffiti-covered Cadillacs rise from the desert in one of Route 66’s most iconic stops. Continue west through Adrian, the official midpoint of the Mother Road, and past the ghost town of Glenrio before climbing into New Mexico’s high desert. By afternoon, you’ll arrive in Santa Fe, one of America’s oldest and most atmospheric cities.
With two nights here, you’ll have time to wander the adobe-lined streets around the historic Santa Fe Plaza, browse the galleries of Canyon Road, or explore local landmarks such as the Cathedral Basilica or the Palace of the Governors. Enjoy authentic New Mexican cuisine, vibrant arts, and a relaxed desert evening before continuing your Route 66 ride.
2 Nights in
Santa Fe, NM
300 miles
Day 9: Gallup, New Mexico
Rio Grande crossings, desert mesas and a historic trading town
Leaving Santa Fe, you ride toward Albuquerque, New Mexico’s largest city, often following old alignments of Route 66 that now form Central Avenue through town. After crossing the Rio Grande, the road rises into high desert dotted with lava fields and sandstone mesas; optional stops may include viewpoints over El Malpais National Monument or quirky roadside cafés that feel frozen in time. Continuing west, you reach Gallup, long known as “the Indian Capital of the World” for its many Native American trading posts and markets. Historic hotels here have hosted Hollywood film stars and road-trippers since the glory days of Route 66, and tonight you’ll soak up that same frontier-meets-Mother-Road atmosphere.
1 Night in
Gallup, NM
270 miles
Day 10: Grand Canyon National Park
Petrified Forest, Painted Desert and a Grand Canyon sunset
Today is packed with variety. Crossing into Arizona, you’ll have the chance to ride through Petrified Forest National Park and the neighbouring Painted Desert, where rainbow-coloured badlands and ancient fossilised logs create an almost otherworldly landscape right alongside historic Route 66. Classic stops like Holbrook’s Wigwam Motel, with its concrete teepees, and Winslow’s “Standin’ on the Corner” park — immortalised in the Eagles’ song — add fun photo opportunities. By afternoon you’ll leave Route 66 at Flagstaff and head north toward Grand Canyon National Park. Your lodge is close to the South Rim, so you can stroll to viewpoints for a jaw-dropping sunset as the canyon walls glow in shades of gold, orange and purple.
1 Night at
Grand Canyon, AZ
285 miles
Day 11: Laughlin, Nevada
Seligman, Hackberry, Oatman and the Colorado River
Early risers can catch sunrise at the Grand Canyon, when the first light spills across the vast chasm and reveals its incredible depth and colours. Later, you’ll rejoin Route 66 at Williams and ride one of its best-loved stretches through Seligman and Hackberry, where gift shops, diners and vintage signs celebrate the revival of the historic highway. Continuing through Kingman, you climb into the rugged Black Mountains toward Oatman, a former mining town where semi-wild burros wander the streets and mock gunfights sometimes entertain visitors. Your day finishes in Laughlin on the banks of the Colorado River, where casino hotels, riverfront walks and desert sunsets provide a fun contrast to the previous night’s national-park tranquillity.
1 Night in
Laughlin, NV
255 miles
Day 12: Las Vegas, Nevada
Hoover Dam, Mojave views and the neon capital of the world
Today you cross the Mojave Desert, with long stretches of open road and far-reaching views that really bring home the scale of the American West. Near the Arizona–Nevada border you’ll ride over, or stop close to, Hoover Dam — an engineering marvel spanning the Black Canyon of the Colorado River, completed in the 1930s and still powering much of the region today. From here it’s a short ride into Las Vegas, where the Strip blazes with neon lights, themed resorts and non-stop entertainment. After parking up the bikes, you can wander among the famous casinos, catch a spectacular show or simply watch the Bellagio fountains dance — an unforgettable mid-tour highlight.
1 Night in
Las Vegas, NV
130 miles
Day 13: Victorville, California
Ride the Mojave and celebrate your final night on the trail
Leaving Las Vegas, you head back into the Mojave, trading glittering lights for wide-open desert vistas as you cross into California — your eighth and final Route 66 state. The ride today really connects you with the experience of early cross-country travellers, who tackled these same arid landscapes long before air-conditioned cars were standard. Stops might include classic truck stops, derelict motels and weather-beaten signs that tell stories of the road’s boom years. By afternoon you’ll reach Victorville in the high desert, home to the California Route 66 Museum and a fitting place to reflect on how far you’ve ridden since leaving Chicago.
1 Night in
Victorville, CA
280 miles
Day 14: Los Angeles / Santa Monica
End of the Trail — Santa Monica Pier celebration
Your final riding day takes you along the last official stretch of Route 66 into the Greater Los Angeles area. As traffic builds and palm trees line the boulevards, excitement grows: you’re approaching Santa Monica Pier, the famed western terminus of the Mother Road. After carefully navigating city streets, you’ll roll onto the pier area and gather beneath the “End of the Trail” sign for celebratory photos with your bike and group — a proud moment marking the completion of roughly 2,800 unforgettable miles. With the riding complete, there’s time to explore Los Angeles highlights such as Hollywood Boulevard, the Walk of Fame, Beverly Hills or Venice Beach, depending on your flight schedule. Tomorrow morning you’ll head to the airport for your overnight flight back to the UK, taking home incredible memories and perhaps already planning your next ride.
1 Night in
Los Angeles, CA
125 miles
We recommend adding an extra night at the beginning and end of your trip to make the journey smoother and more relaxed. Just let us know if you’d like this included in your quote.
We would expect maximum temperatures to be in the 20°C - 30°C range in the midwest and 25°C - 35°C in the south and southwestern states
Flight times to/from Chicago is around 8 hours and Los Angeles is approx 11 hours. You’ll drive through 3 time zones. Chicago is 5 hours and Los Angeles is 8 hours behind the UK.
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