Route 66 Motorcycle Group Tour (East)
7-night guided Harley-Davidson® ride along Route 66 from Chicago to Albuquerque through six states.
Start your engines in Chicago and embark on an unforgettable 7-night guided motorcycle journey along the iconic Route 66 to Albuquerque. From the skyscrapers of the Windy City through the heartland of Illinois, across the Missouri-Ozark hills, into the vast plains of Oklahoma and the Texas Panhandle, you’ll feel the spirit of America’s “Main Street”. Legendary stops include the Gemini Giant, the Chain of Rocks bridge over the Mississippi, the Blue Whale of Catoosa and the art-installation Cadillacs in the desert.
The tour includes late-model motorcycle rental, a professional guide, support vehicle for luggage, breakfast on riding days and iconic sights along the way. Ride with fellow motorcycle enthusiasts, stay in biker-friendly hotels, and soak up the nostalgia of motels, neon signs and two-lane highways. Whether you’re ticking a bucket-list route or simply chasing freedom on two wheels, this ride delivers a compact, high-impact taste of America’s legendary highway.
Our prices include optional insurances
Tours run on selected dates April - October
Single rider or Rider + Pillion options
7 night motorbike group tour from £3,313pp including flights
Highlights
Ride one of the world’s most legendary highways – the original Route 66 from Chicago to Albuquerque.
Cruise in style on a late-model Harley-Davidson with a full support team, professional guide and luggage vehicle.
Visit iconic stops including the Gemini Giant, the Chain of Rocks Bridge, Cadillac Ranch and the Route 66 Midpoint marker.
Experience varied landscapes: the Midwest farmlands, the Ozark hills, Oklahoma plains and New Mexico’s high desert.
Your itinerary
Day 1: Arrive Chicago
Windy City welcome and tour briefing
Arrive into Chicago, Illinois — the birth-place of America’s most celebrated highway. Settle into your hotel, relax after your flight and this evening meet your tour guide and fellow riders at a welcome dinner. Take the time to wander the Michigan Avenue skyline, grab a deep-dish pizza or visit a blues club to feel the city’s rhythm before your bikes hit the road 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
First ride on the Mother Road
Pick up your Harley-Davidson this morning and head out from Chicago along the historic Pontiac Trail, the first alignment of Route 66. Stop in Joliet for the Gemini Giant statue and in Pontiac for its Route 66 Hall of Fame and museum. The afternoon ride leads you into Springfield, Illinois’ state capital, where Abraham Lincoln’s legacy awaits. Soak in the vintage highway atmosphere and settle into your evening.
1 Night in
Springfield, IL
200 miles
Day 3: St Louis, Missouri
Cross the Mississippi & ride the “Gateway to the West”
Today you ride through the Illinois countryside, cross into Missouri and enter St. Louis via the historic Chain of Rocks Bridge — once part of original Route 66 over the Mississippi. In the city, you may visit the Gateway Arch, take in riverfront views and enjoy local BBQ or live music in one of its legendary clubs.
1 Night in
St Louis, MO
100 miles
Day 4: Joplin, Missouri
Ozark hills, Devil’s Elbow curves and roadside nostalgia
Leaving St. Louis behind, you ride into the Ozark Mountains via winding two-lane sections of the original route. Highlights include Devil’s Elbow and other classic bends, plus roadside stops of yesteryear. Arrive in Joplin, a town reborn after severe storms, but steeped in Route 66 character, perfect for sharing stories and reflecting on the road so far.
1 Night in
Joplin, MO
335 miles
Day 5: Oklahoma City, Oklahoma
Three states in a day & the heart of Route 66
Today’s journey spans Missouri, a short Kansas stretch and into Oklahoma — home to the longest continuous sections of Route 66. You’ll stop at quirky attractions like the Blue Whale of Catoosa and ride across plains that hint at America’s biker heritage. Your destination is Oklahoma City, where the Bricktown district offers lively dining and evening relaxation.
1 Night in
Oklahoma City, OK
255 miles
Day 6: Amarillo, Texas
Old-school Oklahoma 66 and Texan Panhandle horizon
Ride sections of original Route 66 through Oklahoma’s ranching country, including the Chisholm Trail corridor from Yukon and El Reno. Crossing into Texas, the landscape opens to vast plains and big skies. Your evening in Amarillo allows for cowboy-style dinner (perhaps the Big Texan Steak Ranch) and restoration after a long ride.
1 Night in
Amarillo, TX
265 miles
Day 7: Santa Fe, New Mexico
Cadillac Ranch, the Midpoint and high-desert artistry
Day 7 begins with a stop at Cadillac Ranch — ten vintage Cadillacs half-buried in the ground and covered in graffiti, a vivid symbol of Route 66 free-spirit. Ride through the midpoint marker at Adrian and the ghost town of Glenrio as you cross into New Mexico. Arrive in Santa Fe for your first night, with time to enjoy its adobe architecture, arts scene and historic plaza.
Tomorrow you have a short ride to Albuquerque, where your guided tour ends as you return your bike and celebrate the adventure before heading to the airport for your overnight flight home.
We highly recommend an overnight stop in Albuquerque to finish off your holiday, please let us know if you would like this added to your quote.
1 Night in
Santa Fe, NM
300 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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Our team have travelled extensively across the USA & Canada to ensure that they can give first hand, unrivalled experience when discussing our holidays.
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