Best Stops on Route 66 for First-Time Travelers

Imagine firing up your car in downtown Chicago and heading west into history. U.S. Route 66 – the legendary “Mother Road” – was created in 1926 and ultimately stretched 2,448 miles from Chicago to Los Angeles.

In its heyday it linked Midwestern farming towns to the Pacific Coast, symbolizing hope and adventure (immortalized in books, songs and films). Today the old highway is a celebrated scenic byway: modern travelers can still follow the route through dozens of small towns dotted with vintage gas stations, neon diners, and “mom & pop” motels.

Along the way you’ll discover quirky roadside attractions, historic sites and classic cafés (“get your kicks!”), all with the backdrop of changing American landscapes. Route 66 helped pioneer the Interstate era, but even after its 1985 decommissioning it remains a major tourist draw – the National Park Service notes over 250 historic sites along or near the old alignment.

Chicago & Illinois: The journey officially begins at Adams and Michigan in Chicago, where the first Route 66 marker stands. Kick off with breakfast at famed Lou Mitchell’s and snap a photo in Millennium Park before heading south (through Joliet’s art-deco Rialto Theatre and Riverview Gardens, if you like).

Illinois was the first state to fully pave its Route 66 segment, and its 300+ miles are studded with classics. Don’t miss the Route 66 Hall of Fame & Museum in Pontiac, a collection of vintage cars and memorabilia.

Nearby Lincoln, IL is home to Lincoln’s post-Vietnam War-era courthouse and even boasts “the world’s largest covered wagon”. Springfield offers Abraham Lincoln attractions (his home, museum and tomb).

The Illinois stretch ends at the Mississippi River; cross the old Chain-of-Rocks Bridge (a Route 66 detour) into Missouri and continue the ride.

Missouri (St. Louis to Joplin)

Missouri’s 317 miles of Route 66 are a rolling mix of cities and Ozark foothills. In St. Louis, start at the Gateway Arch – the soaring 630-foot stainless steel monument nicknamed the “Gateway to the West,” which draws over a million visitors a year.

Nearby is the classic Ted Drewes frozen custard stand (a decades-old Route 66 fixture) and the Donut Drive-In with its giant donut sign. Just west of the city is Route 66 State Park (in Illinois) with preserved old road segments, or drive the Old Chain-of-Rocks Bridge across the river for a photo stop.

Leaving the metro behind, small-town Cuba, MO is “Route 66 Mural City,” designated for its dozen+ colorful mural paintings. Its neon-lit Wagon Wheel Motel (dating from the 1930s) is another classic attraction. A few miles up the road, Devil’s Elbow features an iron truss bridge over the Big Piney River – a picturesque “bad bend” (Elbow Inn saloon nearby) made famous on 66.

Further west, check out Meramec Caverns near Stanton – a sprawling limestone cave system once advertised by dozens of roadside barn ads – considered “one of the primary attractions along former U.S. Highway 66”. Finally arrive in Springfield, MO, the “Birthplace of Route 66,” where you can visit the local Route 66 museum, and learn more about the road’s history in this young city.

Kansas (Galena, Baxter Springs)

Route 66 clips the southeast corner of Kansas (only ~13 miles). Don’t blink – you’ll pass through Galena and Riverton before hitting Baxter Springs. Even in this short stretch, there’s fun stuff: see the “Cars on the Route” exhibit in Galena (the old Kan-O-Tex service station and a Lightning McQueen-type car made famous by Pixar).

Admire the red-and-white 1923 Rainbow Arch Bridge over Brush Creek – the state’s only remaining Marsh Arch bridge (it still carries highway traffic). In Baxter Springs, the restored 1930s Phillips 66 station now serves as the Route 66 Visitors Center and nearby Heritage Museum. All are reminders that even Kansas’ brief 66 portion is packed with road-trip folklore.

Oklahoma (Quapaw to Texola)

Oklahoma contains the longest continuous original stretch of Route 66 (377 miles from the OK line to Texola). Expect easy driving past “charming towns, roadside diners and quirky attractions”.

Early on, stop in Catoosa to see the famous Blue Whale (a giant concrete whale sculpture in a pond) – Atlas Obscura notes it’s become “one of the most recognizable attractions on old Route 66”.

In Tulsa, take a detour north to the Arcadia Round Barn (a restored 1898 wooden barn on a Route 66 spur) and a glass-front diner called Pops 66 (with an oversize soda-bottle sign).

Clinton hosts the official Oklahoma Route 66 Museum (a large hall of historic vehicles and neon signs). Elk City has a huge roadside National Route 66 Museum complex.

Stroud, OK boasts the Rock Café (built of native rock in 1939) – still a popular 66 diner. By mid-route look for Arcadia again (east of OKC): the revived John’s Place gift shop with its neon guitar sign. Finally roll through Oklahoma City (see Bricktown, or the sobering Oklahoma City National Memorial downtown) before heading west. Even after I-40 opened, the old highway here is well-marked and full of nostalgia.

Texas (Panhandle: Texola to Glenrio)

Crossing into Texas at Texola, you enter the panhandle's windswept plains. In Shamrock, TX, visit the restored 1936 art-deco Tower Station & U-Drop Inn (now a visitor center) – its neon curves inspired the “Ramone’s” garage in Cars.

A bit west, McLean is home to the Texas Route 66 Museum (with original Route 66 signs and even the steer from Amarillo’s Big Texan) and the Devil’s Rope (barbed wire) Museum in one building. Stop in Groom to see the Leaning Tower of Texas (a tilted water tower placed by artist/gourmet Ralph Britten).

Amarillo is the biggest city on the Texas Route 66. Here, Historic Sixth Street (old 66) is a shopping/dining district, but the big draws are a bit out of town: Cadillac Ranch (a 1974 pop-art installation of ten half-buried classic Cadillacs along I‑40) is a must-see.

Nearby is the Big Texan Steak Ranch – famous for its free 72‑ounce steak challenge – a kitschy Texas icon. Also in Amarillo you’ll find a Route 66 Visitor Center (in an old Myrtle chicken-house restaurant) and neon motels. Continuing west, the tiny towns of Vega and Adrian (the exact midpoint of Chicago–LA, 1,139 miles each way) offer photo ops.

End the state at Glenrio, a dusty former boom-town on the NM border with abandoned motels (the state line runs down Main Street).

New Mexico (Glenrio to Gallup)

Entering New Mexico, the road climbs over mesas and plains (from ~3,800 to 7,200 ft). In the east, Tucumcari is often called the “motel capital” – it’s famous for dozens of vintage neon signs and motels (including the legendary Blue Swallow Motel).

Town murals abound (Tucumcari has painted “Get Your Kicks on Route 66” murals and more). Further west, stop in Santa Rosa for a swim in the crystal-clear Blue Hole, a natural artesian spring beloved by divers. The Santa Rosa Route 66 Auto Museum (in an old gas station) has classic cars and Route memorabilia.

At Santa Fe you have an option: the original 1926 alignment headed 50 miles north into Santa Fe (with beautiful adobe Plaza, historic Loretto Chapel, etc.), but the main Route 66 bypassed it after 1937 via Clines Corners. A short detour allows you to see Santa Fe’s Spanish colonial core.

Continue on to Albuquerque (Old Town Plaza, Route 66 neon on Central Ave., Sandia Peak Ski Area above town). At the Continental Divide near Thoreau (7,275 ft), you’ll literally pass the line between the Atlantic and Pacific watersheds. Finally Gallup, NM, is the largest city on 66 between Albuquerque and Flagstaff.

Here the glamour is Southwestern culture: Gallup brags over 100 Native American trading posts and a Hotel El Rancho (built in the 1930s, once hosting movie stars). The Gallup Cultural Center (old Santa Fe train depot) and Red Rock Park offer more Old West charm.

Arizona (Lupton to Topock)

Arizona’s 400+ miles are among the most iconic. Just past the NM line, Holbrook puts you at the gates of Petrified Forest National Park (and Painted Desert) – the only national park on Route 66.

Holbrook itself hosts Wigwam Motel #6, where you can sleep in concrete teepees (one of only two such motels left on 66). West of Holbrook, another unmissable stop is Winslow: pose “Standin’ on a Corner” (a park/mural from the Eagles song) and admire restored downtown neon.

A short drive west brings you to Meteor Crater, a 3,900‑foot-wide impact crater that makes for an otherworldly detour.

Next Flagstaff (7,000 ft elevation) is a cool mountain town and a key hub: from here you can side-trip to the Grand Canyon (the Williams–Grand Canyon Railway departs nearby).

Flagstaff’s Historic Route 66 Visitor Center (on Rt 66 itself) has maps and memorabilia. Leaving Flagstaff, the road follows today’s I‑40 through Williams (the “Gateway to the Grand Canyon”) to Ash Fork. In Seligman, Arizona (population ~450), Angel Delgadillo and his wife Vilma have recreated a retro 1950s main street – it even calls itself “The Birthplace of Historic Route 66”.

Their gift shop, diner and the classic Aztec Motel sign are must-see throwbacks. Farther west lie small names like Peach Springs and Hackberry – here the old neon signs and general stores evoke ghost-town charm.

In Kingman, AZ, Route 66 is well-preserved: the Arizona Route 66 Museum and Powerhouse (at the Visitor Center) chronicle the road’s saga. Kingman is also our last large town before the Colorado River.

From Kingman, pick up old US 66 (now “Oatman Highway”) through the sinuous Black Mountains: you’ll climb over Sitgreaves Pass and then descend into the restored ghost town of Oatman, AZ. Oatman’s wooden storefronts and roaming wild burros (descended from miners’ pack animals) make a memorable end to the Arizona portion.

California (Needles to Santa Monica)

Crossing the Colorado River at Topock, you’re in California’s Mojave Desert. Early stops include the ghost town of Amboy (Roy’s Motel Café with its iconic 1950s neon sign) and isolated desert hamlets like Ludlow.

By Barstow (66’s western junction), visit the Route 66 Mother Road Museum (in the historic train depot). Nearby off-route are roadside oddities like Elmer’s Bottle Tree Ranch (forest of glass-and-metal “trees”). As you head south through the High Desert (Victorville, San Bernardino County), consider a quick detour to the last surviving Wigwam Motel (in San Bernardino) – more teepees like its Holbrook cousin.

Just off old 66, the site of the original McDonald’s in San Bernardino has been converted to a museum of golden-arch history.

In Greater Los Angeles the old road becomes Foothill Boulevard and Arroyo Seco Parkway. Finally, Route 66 pulls into Santa Monica: stand on the Pacific at the Santa Monica Pier, beneath the “End of the Trail” sign.

A plaque and neon “Route 66 End of the Trail” sign mark the symbolic terminus – congratulations, you’ve traversed America’s Main Street!

Planning and Practical Tips

• Timing: The best seasons are late spring or early fall. Many guides recommend running Route 66 from April/May through early July, then again in September–October. These shoulder seasons avoid winter snows in the upper Midwest and punishing summer heat in the desert. Summer (July–August) brings crowds and monsoons, while winter snows can close northern stretches (Arizona’s Flagstaff and parts of New Mexico).
• Duration: Don’t rush. The raw driving time Chicago–LA is ~32–38 hours nonstop, but sightseeing slows you down. Route 66 experts advise 200 miles per day if you want to explore. In practice that means 10–12 days minimum for a hurried trip, but 14–21 days (or more) is ideal. Allow extra time for side trips (Grand Canyon, Santa Fe, Las Vegas, etc.) and roadside detours.
• Car and Route: A comfortable, reliable vehicle is key (renting in Chicago and dropping off in LA/Santa Monica is common). Many travelers like convertibles for the wind-in-hair experience. Fill up often: some desert stretches have no gas for 75+ miles. A detailed map or GPS/phone app is essential – although Route 66 is signed in most states, the old alignments sometimes weave on and off the Interstate. Bring water and snacks for lonely stretches, and keep an eye on weather (thunderstorms and flash floods happen in the summer).
• Lodging: Route 66 is famed for its vintage motels, from neon roadhouses to classic motor courts. In peak season or remote towns (like Holbrook or Seligman) book ahead if possible. Many small-town motels have only a handful of rooms. Alternately, campgrounds and RV parks are plentiful in rural areas.
• Attractions: Many attractions on Route 66 are free (roadside statues, historic signs, parks). Some (museums, caverns, the Grand Canyon, Petrified Forest) charge admission. Check opening hours – many Route 66-themed businesses close in winter. Carry a few dollars for tolls (Missouri and Illinois turnpikes) and small purchases (roadside cafes love cash).
• Culture: Be ready for kitsch and nostalgia. Route 66 is as much about Americana and local color as scenery. Enjoy quirky diners, “shootouts” at western towns, and impromptu honky-tonks. Chatting with local owners at a decades-old café or filling a vintage gas pump is half the fun. Keep a camera handy – the whole route is a living photo museum.

Sample 2-Week Itinerary (Day-by-Day)

For a leisurely trip, consider 12–14 days. For example, one plan might be:

Each day covers 150–250 miles; adjust based on your pace. Feel free to swap towns or linger where you please – the legend of Route 66 invites a relaxed road-trip spirit.

This guide draws on up-to-date travel resources and Route 66 preservation groups. For detailed state-by-state information see route66roadtrip.com’s state guides and the National Park Service’s Route 66 Corridor program. Ride safely, keep an open mind, and get your kicks on Route 66!