Collection of old photographs showing group snapshots, including a Phillips 66 landmark and roadside scenes

ROUTE 66: A TESTAMENT TO THE SPIRIT OF THE OPEN ROAD

Written by The Harley-Davidson Museum
Photos by Josh Kurpius Archival photos courtesy of H-D Museum

Few roads in the U.S. capture the imagination quite like Route 66. For nearly a century, it has represented a distinctly American fascination with movement, discovery, and life beyond the horizon — an idea Harley-Davidson riders have always understood.

Route 66 earned the nickname "Mother Road" in John Steinbeck's The Grapes of Wrath, but its story began long before it became an American icon. Established in 1926 as part of the federal highway system, the route stretched more than 2,000 miles across eight states, linking small towns, major cities, and everything in between.

Travelers came first. Then came the gas stations, diners, motor courts, and roadside attractions. Mile by mile, a highway built to connect the country helped create an entire culture around the open road.

Though you might expect the Harley-Davidson Archives to contain a trove of early Route 66 photographs, most of what we find from the road's first decades are passing references in touring stories published in The Enthusiast. In these accounts, Highway 66 is simply part of the route — a well-known road riders happen to travel on their way somewhere else.

“WHEN I WAS 12, I TRAVELED ROUTE 66 WITH MY PARENTS IN A 1957 PLYMOUTH. I REMEMBER FALLING DEEPLY IN LOVE WITH A TRUCK STOP WAITRESS WHO BROUGHT ME A CHOCOLATE MILKSHAKE. THIRTY NINE YEARS LATER, I FELL IN LOVE ON OLD 66 AGAIN, THIS TIME WITH AMERICA.”

- Hog Tales, Sept.-Oct. 1996

Over time, that began to change. By the time Harley Owners Group® (H.O.G.®) entered the picture in 1983, the road itself had become the destination. Route 66 has hosted countless H.O.G. rides and rallies, but organized tours tell only part of the story.

Many riders simply wanted to be able to say they'd ridden it.

“With my mission accomplished, I headed south into Arizona toward Route 66, just so I could say I rode on that famous road (and to “stand on a corner in Winslow, Arizona”),” wrote H.O.G. member Dennis Daniels in the July-August 2008 issue of Hog Tales.

Hermann J. Jakob of Cologne, Germany, used the Fly’n’Ride program to travel to the U.S. and made sure to take a spin from Kingman to Seligman in 2002.

Alex Chacón rode Harley-Davidson's Project LiveWire along Route 66 for six days, writing about the electric adventure in Volume 27 2014 issue of HOG magazine.

Two riders travel a curving road, one wearing a Route 66 vest, captured from behind in a vintage photo

But some people want to experience it all.

“When I was 12, I traveled Route 66 with my parents in a 1957 Plymouth. I remember falling deeply in love with a truck stop waitress who brought me a chocolate milkshake. Thirty nine years later, I fell in love on Old 66 again, this time with AMERICA.” — Hog Tales, Sept.–Oct. 1996

In 1996, 425 riders left Milwaukee on June 7, and by the time they rumbled into California on the 21st, 3,000 people had participated in the "Ridin' Route 66" tour, including those who nabbed day passes and joined city stopover festivities.

The tour celebrated 70 years of Route 66 and sparked a scrapbook-worthy story in the 1996 Sept-Oct issue of Hog Tales, filled with memories shared through photos and quotes.

Close-up of 1996 Route 66 pins displayed in a case, featuring various HOG rally locations and badges
Vintage photo of two people standing beside parked motorcycles beneath a Historic Route 66 road sign
Vintage photo of person lying on pavement next to a painted Route 66 marker
Vintage photo of public art installation Cadillac Ranch - a row of ten old Cadillacs buried nose-first in the ground and covered in grafitti

ROUTE 66 ALOWS RIDERS TO SET THEIR PACE AND SAVOR THE JOURNEY, OFFERING NEON SIGNS, QUIRKY ROADSIDE ATTRACTIONS, AND REGIONAL CUISINE AT NEARLY EVERY STOP.

The 75th anniversary of the Mother Road inspired the 2001 National H.O.G. Touring Rally Made In America: Route 66.

“This road of John Steinbeck, Woody Guthrie, Jack Kerouac, Mickey Mantle, and so many others is still the best path for drifters, dreamers, and pilgrims on a quest. The road paid its dues and evolved into a timeless monument to the people of the road and all that travel its length. This summer, the bold riders from around the world who answer the call and join H.O.G. in Chicago for the ride of their lifetime will know exactly what I mean.” — Michael Wallis, author and Route 66 historian, Hog Tales, Jan.–Feb. 2001

Those who registered for the ride that took place June 23 through July 8 could receive a commemorative t-shirt, silver Route 66 wings pin, pin set, illustrated map set, and a special edition watch.

Large crowd of 2001 Route 66 riders fills grandstand seating at an outdoor venue, captured as a wide group photo
Bright red Harley Owners Group Route 66 2001 banner covered in handwritten signatures and messages
Close-up of a Harley Owners Group Route 66 2001 themed wristwatch displayed in a box, with a black leather strap

In 2010, H.O.G. returned to Route 66 for the late summer "Motoring the Mother Road" tour. Like the rides that came before it, the journey gave participants the chance to experience the Mother Road alongside fellow Harley riders while collecting a few keepsakes along the way, including state-by-state helmet stickers, commemorative pins, maps, and other Route 66 memorabilia.

Illustrated poster promoting Harley Owners Group Route 66 “Motoring the Mother Road” tour with desert road and retro styling
Close-up of a winged 2010 Route 66 badge pin with Harley Owners Group branding on a dark background
Sheet of 2010 Route 66 themed stickers laid over a signed red HOG banner with handwritten notes
Black cap with embroidered Route 66 Harley Owners Group 2010 logo resting on a red signed banner
Vertical Route 66 pennant with stops in different cities marked along a route in the center
Detail of commemorative black t-shirt with collage of Route 66 themed graphics

Route 66 allows riders to set their pace and savor the journey, offering neon signs, quirky roadside attractions, and regional cuisine at nearly every stop. It takes you past ghost towns and major cities, through stretches of desert, winding mountain passes, and open plains.

Wind, rain, snow, and sunshine come with the territory. So do the junebugs, goats, and spiders. It creates a community of likeminded people who feel the pull of nostalgia and the thrill of exploration — just ask the group of women who rode, wrenched, and wandered the road for two weeks in 2022.

Although Route 66 was officially decommissioned as a federal highway in 1985, it never really disappeared. Harley-Davidson riders continue to seek it out, whether for a few memorable miles or the journey from end to end. From adventuring solo or joining a H.O.G. rally, Harley-Davidson riders have done their part to keep Route 66 alive and document the experience along the way.

Nearly a century after it first appeared on a map, Route 66 remains what it has always been: an invitation to see what waits around the next bend.

EXPERIENCE THE HISTORY OF HARLEY-DAVIDSON


Discover culture and history through stories and exhibits that celebrate expression, camaraderie and love for the sport.  

The logo structure outside the Harley-Davidson Museum

EXPLORE MORE FROM THE ARCHIVES

Vintage photo of Gustaf Stenmark seated on a classic motorcycle with saddlebags, parked overlooking hills and water in the distance

“MOTORCYCLING IS THE LIFE”: THE LEGACY OF GUSTAF STENMARK

Driven by an obsession with motorcycles, Gustaf Stenmark pushed himself through every race and mile with competitive grit, chasing the limits of endurance on two wheels.

Black-and-white photo of a motorcyclist procession riding toward the U.S. Capitol, laying among papers

HARLEY-DAVIDSON RIDES FOR LIBERTY

As the Statue of Liberty prepared for her 100th anniversary, Harley‑Davidson riders united coast to coast to celebrate freedom and help restore an American icon.

Close-up of black leather vest covered in pins, featuring a colorful embroidered Charter Life Member AMA patch

FROM WAISTCOAT TO CUT: THE EVOLUTION OF THE MOTORCYCLE VEST

The vest may have started out as a practical piece of clothing worn by aristocrats and soldiers, but today, it's one of the most iconic symbols of motorcycle culture.

Black-and-white photos of vintage motorcycles, including a HarleyDavidson ’76 Bicentennial tank logo

THE '76 BICENTENNIAL EDITION: THE BIRTH OF AN ICON

The 1976 Liberty Edition fused American patriotism with Harley‑Davidson craftsmanship, creating a landmark design that still resonates as a symbol of freedom and identity.

Exhibit at the Harley-Davidson Museum featuring vintage motorcycles mounted on a curved section of board track with historic photos

LIFE ON THE MURDERDROME: H-D AND THE SPORT THAT TERRIFIED EVERYONE

Long before racing glory, Harley-Davidson’s uneasy entry into board track competition was lived on the edge by riders like L.E. Bowen.

Vintage motorcycle magazines and documents including a 1960 Daytona Motorcycle Show booklet

FLASHBACK: STEP INSIDE THE DAYTONA 1960 MOTORCYCLE SHOW

Daytona Bike Week celebrates its 85th year, offering the perfect moment to look back at the rally’s iconic 1960 roots.

Alfonso Sotomayor’s 1957 Harley-Davidson FL on display in the H-D museum archives.

ALFONSO SOTOMAYOR AND MEXICAN STUNT RIDING

Harley-Davidson’s century-long history in Mexico is filled with pioneering riders and legendary stunt performers like Alfonso Sotomayor.

A vintage leather motorcycle helmet with a wing shape on the front is displayed on a table surrounded by black and white archival photos of riders.

HELMETS THROUGH HISTORY

From humble leather caps to modern safety gear, the evolution of motorcycle helmets balances protection, performance, and pure self-expression.

A vintage black and white group photo of the Motor Maids in front of a large Holiday Inn sign and marquee that says “Welcome Motor Maids” during a rally in 1967.

RIDING FORWARD: 85 YEARS OF THE MOTOR MAIDS

Founded in 1940 by pioneers Dorothy “Dot” Robinson and Linda Dugeau, the Motor Maids became the first women’s national motorcycle club.

 Black and white historical photo of Eldred Harrington standing by his 1951 Harley-Davidson Hydra Glide motorcycle in the desert.

RIDING THROUGH HISTORY: ELDRED R. HARRINGTON’S HARLEY-DAVIDSON ADVENTURES

Eldred R. Harrington, a prolific Enthusiast writer from 1944–1965, was revisited by Harley-Davidson archives during the Hydra-Glide’s 75th anniversary.

A collection of vintage motorcycle gear including leather helmets, goggles, boots, and wool clothing.

EARLY RIDING WEAR

In the earliest images in the Harley-Davidson archives, riders’ clothing always stands out.

An old photograph shows Leslie “Red” Parkhurst sitting on his Harley in his riding gear.

LESLIE “RED” PARKHURST

Parkhurst was a good-natured athlete whose enthusiasm made him a real crowd-pleaser, both on and off the track.

Eight men in black Harley jackets stand behind the Sportster streamliner in the desert.

THE WORLD'S FASTEST HARLEY-DAVIDSON

Built for Speed. Born for Glory. The Return of a Legend.

Soldier uses his motorcycle as a barrier to prop his rifle on

HARLEY-DAVIDSON DURING WWII

A brief look at how the Harley-Davidson Motor Company, employees and riders contributed to the war effort.

Harley-Davidson's founders pose for a photo

THE FOUNDERS OF HARLEY-DAVIDSON

They could have scarcely imagined what they had started.

Willie G poses with a paintbrush

WILLIE G. DAVIDSON

A tireless artist, enthusiastic rider, and grandson of a co-founder of the Harley-Davidson Motor Company.

Two racers battle for the lead on a round track

10 PEOPLE YOU SHOULD KNOW FROM HARLEY-DAVIDSON HISTORY

Countless riders, employees, and fans have been at the heart of Harley-Davidson's 120 year history.

A vintage leather jacket on a mannequin

120 YEARS OF STYLE

From instant icons to just plain cool: a glimpse at historic Harley-Davidson® apparel.

Juneau Avenue headquarters under construction

BUILDING A MILWAUKEE ICON

Explore the legendary campus that remains Harley-Davidson's headquarters through this look at how the Juneau Ave. factory developed from 1906 through the 1920s.