Walking Historic Route 66

Day 1

Arrive Chicago, Illinois

Our Adventure along Route 66, referred to by John Steinbeck as “the mother road” and “America’s Main Street,” begins today in Chicago. The only activity planned for today is a “Get Acquainted” briefing at our hotel around 7:30 pm.

Day 2

Chicago–Bloomington, Illinois (BD)
Chicago Windy City Walk, IL – 11 km, rated 1+

Today’s activities start with breakfast at Lou Mitchell’s Restaurant, a Chicago institution since 1923. Our walk includes Windy City classics like the Shedd Aquarium, the Field Museum, the John Hancock Building, and the Magnificent Mile along Michigan Avenue. Following the walk, our pilgrimage–a 2,400 mile odyssey to Santa Monica, California, where the road ends–begins with a stretch southwest along the original road to dinner at the Old Log Cabin Inn in Pontiac.

Day 3

Bloomington-Springfield (BL)

Breakfast at Dixie Trucker’s Home shows us how an icon of Route 66 started in 1928 from a converted garage and has adapted through 75 years of change. Further south in Amish country, we visit the Amish Interpretive Center, then take a drive through the countryside of the Amish community in Illinois, learning about the local lifestyle and culture from our guide as we pass Amish homes, businesses, farms, and schools. Following lunch in an Amish home (homemade everything!), the lady of the house shows us through her home, describing daily tasks and detailing their form of worship. Leaving idyllic Amish country, we spend the night in Springfield, Illinois, home of Honest Abe. You may have time to visit the new Abraham Lincoln Museum or Abraham Lincoln Presidential Library, or you may choose to include this in tomorrow’s walk route.

Day 4

Springfield–St. Louis, Missouri (B)
Abe Lincoln Springfield Walk, IL – 10 km, rated 1

Our Springfield walk traces the heritage of Abraham Lincoln with stops at Lincoln’s Tomb, the state capitol, and the Lincoln Home. After a stop for a Route 66 lunch (not included) at Cozy Dog Drive-In, where corn dogs were first created, we’ll cross the border to St. Louis, with a stop en route at the Chain of Rocks Bridge.

Day 5

St. Louis–Rolla, Missouri (B)
St. Louis Amazing Arch Walk, MO – 10 km, rated 1

This morning’s walk features the city that was considered a major gateway to westward migration in the century before Route 66. Our walk route in St. Louis passes both the Jefferson National Expansion Memorial (free admission) and the famous Gateway Arch (admission not included), before our mid-afternoon departure along the Old Road.

Day 6

Rolla–Miami, OK (BL)
Wilson Creek National Battlefield Walk, MO – 10 km, rated 2

Route 66 leads us diagonally across Missouri to Wilson’s Creek National Battlefield, site of one of the most important early battles in this epic conflict between the States. Following our walk, and an enlightening visit to the National Parks interpretive center, we’ll enjoy a down-home lunch at a fun eatery nearby before continuing along the highway into Oklahoma.

Day 7

Miami–Edmond, Oklahoma (B)
Riverton Rainbow Bridge Walk, KS – 10 km, rated 1

The state of Kansas lays claim to only 13 miles of the Route, and we’ll cover a good percentage of that on this morning’s walk that includes a stroll across Rainbow Bridge, a classic Route 66 landmark. A lunch break at the Eisler Bros. Old Riverton Store (est. 1925) is the only appropriate way to finish this walk. Across the state line in Claremore, Oklahoma, we’ll pause at the Will Rogers Memorial Museum to reflect on the life of this beloved humorist.

Day 8

Edmond–Clinton, Oklahoma (B)
Oklahoma City “OKC” Walk, OK – 10 km, rated 1+

After a short stop at The Round Barn, one of many fun, quirky icons of Route 66, we continue into OKC, as the locals call it, for our Oklahoma City Walk. Featured along the trail are the seven-story, cylindrical Crystal Bridge at Myriad Botanical Gardens (admission not included) and the Oklahoma City National Memorial, eulogizing those lost in the tragic bombing of 1995.

Day 9

Clinton–Amarillo, Texas (BD)

One of our favorite Route 66 museums is near our hotel in Clinton. After some time at this nostalgic window into the Oklahoma of yesteryear, America’s Main Street leads us into the Texas Panhandle. En route to Amarillo, the Devil’s Rope Museum (aka “barbed wire”) fills a surprisingly interesting gap in our knowledge of western lore. A memorable visit to a local cattle ranch this evening includes a fun cowboy dinner and introduces us to the larger-than-life legends of the Lone Star State.

Mother Road Out West: Amarillo-Santa Monica

Day 10

Amarillo–Santa Fe, New Mexico (B)
Amarillo Panhandle Walk, TX – 10 km, rated 1

Following a Texas-sized breakfast at the Big Texan Steak Ranch, our walk for the day explores the parks and neighborhoods along historic Route 66 in Amarillo. Continuing our westward pilgrimage, we’ll stop for a photo of the eclectic Cadillac Ranch then pay homage at the remains of Glenrio, a Route 66 ghost town straddling the Texas/New Mexico border. A brief stop in the Mother Road town of Tucumcari, an early supper at the Lake City Diner in Santa Rosa, and a scenic drive north to Santa Fe round out another classic day on the Road.

Mother Road in the Heartland: Chicago–Amarillo

Day 11

Santa Fe–Albuquerque, New Mexico (B)
Santa Fe Spanish Heritage Walk, NM – 10 km, rated 1+

The majority of today is devoted to a popular walk through New Mexico’s capital, the oldest town (established in 1610) west of the Mississippi. A captivating weave of Native American, Spanish, and Anglo cultures gives travelers insight into the heritage of New Mexico as they stroll past the capitol building, the original Palace of the Governors, and the 17th century San Miguel Mission Church. This evening, we’ll be down the road at the Albuquerque Balloon Fiesta. The largest hot air balloon event in the world draws hundreds of balloonists with crafts of all shapes, sizes, and colors. Tonight’s event is the Glowdeo, when all balloons created in unusual shapes fire their burners and light up at the same time – it’s breathtaking!

Day 12

Albuquerque – Gallup, NM (B)
Albuquerque Balloon Fiesta Walk, NM – 10 km, rated 1

Today’s Fiesta highlight is a Mass Ascension of all balloons, an event claimed to be the most photographed happening in the world! Following this hot air high, we’ll return to town for our walk through Old Town Albuquerque’s shops, galleries, and a stretch of Route 66. The Route from Albuquerque leads west towards Acoma Sky City Pueblo, a native community perched high atop a mesa since AD 1150 in an area of dramatic high-desert landscapes. Access to this oldest continuously inhabited community in North America is tightly controlled; we will visit in the company of a tribal member to learn the traditions and history of the tribe.

Day 13

Gallup – Flagstaff, Arizona (B)
Flagstaff Route 66 Walk, AZ – 10 km, rated 2

We’ll follow the open road westward into Arizona this morning, cruising past old Route 66 settlements like Holbrook before arriving at the Meteor Crater. At 4100 feet in diameter, this privately managed natural wonder is touted as the best-preserved meteorite crater on the planet! Continuing on, we arrive mid-afternoon for today’s walk in Flagstaff. Prior to its Route 66 days, this town’s “flagstaff” marked the trail for wagon trains bound for California.

Day 14

Flagstaff–Needles, California (BL)

We leave Flagstaff today, returning to the Mother Road. Our mid-morning rest stop is in Seligman at the fabled Snow Cap Drive-In Restaurant, a Route 66 icon. One of the best preserved sections of the old road takes us to Kingman for a lunch stop, followed by the steepest portions of the Route that lead to the old mining town of Oatman, known for the semi-wild burros that wander the main street. We’ll overnight in Needles in preparation for tomorrow’s final run to the Pacific!

Day 15

Needles–Santa Monica, California (B)
Hollywood Flats Walk, CA – 11/5 km, rated 1

Beyond Needles, the dreaded heat of the Mohave Desert awaits, feared by drivers of less reliable, older vehicles more than any other stretch of Route 66. We’ll better understand their anxiety as we cruise the parched, unforgiving desert. We’ll stop for a lunch break and our last Route 66 Museum in Victorville before detouring off the Route for a walk along the star-studded streets of Hollywood.

Day 16

Activities in Santa Monica (BD)
Santa Monica End of the Route Walk, CA – 10 km, rated 1

The Mother Road ends at the corner of Santa Monica Boulevard and Ocean Avenue in the popular ocean resort of Santa Monica, a stone’s throw from the waves of the Pacific. Our last walk features the Third Street Promenade, colorful Santa Monica Pier, and Palisades Park. You’ll have all day to explore “the end of the road”– consider a visit to one of Santa Monica’s many museums, enjoy the public murals and other monuments, or sample the shops and restaurants along the pier. Then join us for a Farewell Dinner tonight to reminisce about
our memorable journey along the Mother Road!

Day 17

Return home from Santa Monica (B)

We’ll make our way to the Los Angeles International Airport this morning, saying farewell to our fellow pilgrims before returning to our own corners of America. As the old song goes, we “got our kicks on Route 66,” enjoying a nostalgic dose of the Mother Road and a slice of all things Americana along the way.