Explore/United States/US/Route 66 — Chicago to Santa Monica

USChicago, United StatesModeratePaved8-day tripMotoVault Pick

Route 66 — Chicago to SantaMonica.

Distance

3,940 km

Duration

8 days

Climb

2,400 m

Rating

4.9 / 5

5621 reviews

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Curated by Rider · Updated Jun 2026

Overview

Route 66 — Chicago to Santa Monica.

America's Mother Road end-to-end — 3,940 km from Chicago's Lake Shore Drive to the Santa Monica Pier. Eight days through Illinois, Missouri, Oklahoma, Texas, New Mexico, and Arizona to the Pacific. Neon motels, roadside giants, ghost towns, and the Cadillac Ranch along the way.

Quick facts

SurfacePaved

Distance3,940 km

Days8

Total climb2,400 m

Fuel stops2 along route

DifficultyModerate

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Day-by-day

8 days, 8 moods.

A suggested split across 8 days with 49 waypoints to discover along the way.

DAY 01

Chicago — Millennium Park → Springfield, IL

6 stops

Chicago — Millennium ParkStart · The official Route 66 start is at the intersection of E Adams St and S Michigan Ave. Millennium Park is 300 m away. Fill up in the suburbs before leaving the city.

Joliet — Gemini GiantScenic Point · A 28-foot fiberglass spaceman holds a rocket outside the Launching Pad Drive-In. One of the iconic roadside giants of Route 66 — the road is warming up.

Dwight Standard Oil Gas StationPhoto Spot · A 1932 Sinclair gas station perfectly restored to its original green-and-white livery. The quintessential Route 66 petrol station photograph.

Pontiac — Route 66 Hall of FameRestaurant · Free Route 66 museum in a converted fire station. Pontiac has the best-preserved painted building murals on all of Illinois Route 66. Lunch at a local diner.

Funks Grove Maple SirupScenic Point · A family maple operation since 1824 — the oldest business on Illinois Route 66. The spelling "sirup" (not syrup) is original and intentional. Small chapel in the grove.

Reviews

From riders.

5621 verified rides logged on this route.

4.9/ 5

★ ★ ★ ★ ★

5621 verified rides

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DAY 02

Lincoln's New Salem State Historic Site → St. Louis, MO

6 stops

Lincoln's New Salem State Historic SiteScenic Point · A reconstruction of the 1830s frontier village where Abraham Lincoln lived as a young store clerk and postmaster before entering politics. A quiet, beautiful start to Day 2.

Ariston Café, AuburnRestaurant · One of the oldest continuously operating restaurants on Route 66, open since 1938. The neon exterior is original. Order the fried chicken — it has been on the menu for 80 years.

Chain of Rocks BridgePhoto Spot · A 1929 highway bridge over the Mississippi with a unique 22° bend mid-span — built to align with the current. Now a pedestrian and cycling trail with spectacular river views.

Gateway Arch, St. LouisScenic Point · Eero Saarinen's 192 m stainless steel arch on the Mississippi riverfront — the largest arch in the world. The tram to the top is worth the queue.

Ted Drewes Frozen CustardRestaurant · The most famous stop on all of Route 66 in St. Louis since 1929. The "concrete" frozen custard is so thick it's served upside down. Long queue; entirely worth it.

St. Louis, MOOvernight · Overnight in St. Louis. The Soulard neighborhood has excellent restaurants and live blues music. The Anheuser-Busch brewery tours run daily.

DAY 03

Wagon Wheel Motel, Cuba MO → Joplin, MO

6 stops

Wagon Wheel Motel, Cuba MOScenic Point · A 1934 motor court — one of the most preserved original Route 66 motels in America. The neon sign and individual cabin units are intact. A mandatory photo stop.

Meramec CavernsScenic Point · An enormous cavern system that was a hideout for Jesse James. The cave was advertised on barn roofs all along Route 66 for decades — you've probably seen the logo already.

Rolla, MOFuel Stop · Mid-point fuel stop. The Totem Pole trading post has operated here since 1933. Good fuel prices before the rural stretch into the Ozarks.

Devil's Elbow, MOScenic Point · A sharp horseshoe bend in the Big Piney River where the old alignment twists down a ridge. One of the most technically pleasing curves on all of Route 66.

66 Drive-In, CarthagePhoto Spot · One of the last operating outdoor movie theaters on Route 66, built in 1949. The neon sign and projection tower are beautiful regardless of show times.

Joplin, MOOvernight · Gateway to Oklahoma. The 1950s neon strip on Main Street has been restored. The Joplin Museum Complex covers the 1917 mining boom that built this town.

DAY 04

Cars on the Route, Galena KS → Oklahoma City, OK

6 stops

Cars on the Route, Galena KSPhoto Spot · A rusted 1951 International tow truck that directly inspired Tow Mater in Pixar's Cars. Small diner and Route 66 gift shop alongside.

Claremore — Will Rogers MemorialScenic Point · The birthplace and burial site of Will Rogers — Oklahoma's most famous son. The 1938 memorial museum overlooks the Arkansas River valley.

Tulsa — Cyrus Avery Centennial PlazaScenic Point · A plaza celebrating Route 66's co-creator on the Arkansas River. The "East Meets West" bronze sculpture — a 1920s car meets a wagon — is the centrepiece.

Rock Café, Stroud OKRestaurant · The 1939 sandstone roadhouse that inspired Sally Carrera in Pixar's Cars. Famous burgers on a stretch of beautifully preserved original Route 66 alignment.

Oklahoma City National MemorialScenic Point · The outdoor memorial to the 168 victims of the 1995 bombing. The 168 empty bronze chairs are one of the most moving public memorials in America.

Oklahoma City, OKOvernight · Overnight in OKC. The Bricktown entertainment district is a 10-minute walk from most Route 66 motels. Stockyards City has the best steak in Oklahoma.

DAY 05

Round Barn, Arcadia OK → Amarillo, TX

6 stops

Round Barn, Arcadia OKPhoto Spot · A perfectly circular 1898 barn that survived over a century of Oklahoma storms through geometric structural brilliance. Now a Route 66 interpretive museum.

U-Drop Inn, Shamrock TXPhoto Spot · The most architecturally dramatic building on all of Route 66 — a 1936 art deco tower and sweeping canopy that is now the Conoco station. The inspiration for Ramone's House of Body Art in Cars.

Devil's Rope Museum, McLean TXScenic Point · The world's largest collection of barbed wire — the "devil's rope" that fenced the open range and transformed the American West. Unexpectedly fascinating.

Cadillac Ranch, AmarilloPhoto Spot · Ten Cadillacs buried nose-down in a Texas wheat field since 1974, covered in layers of spray paint. Bring a can and add your mark to America's most democratic public art installation.

Big Texan Steak RanchRestaurant · The Route 66 Amarillo institution since 1960: eat a 72 oz steak dinner in under an hour and it's free. The neon cowboys and longhorn cattle in the parking lot are visible from the highway.

Amarillo, TXOvernight · Overnight in Amarillo. The San Jacinto neighborhood has good craft beer and live music. Tomorrow the road enters New Mexico — landscapes change dramatically.

DAY 06

Glenrio Ghost Town → Albuquerque, NM

6 stops

Glenrio Ghost TownScenic Point · One of the most authentic ghost towns on Route 66 — straddling the TX/NM state line. The diner, gas station, and motel are all abandoned mid-service. Perfectly haunting.

Blue Swallow Motel, TucumcariPhoto Spot · The most beautiful neon motel sign on all of Route 66, in the town with the best-preserved 1950s neon streetscape in the world. Even if you're not staying, stop for the photograph.

Blue Hole, Santa Rosa NMScenic Point · A perfectly circular artesian spring pool of crystal-clear 16°C water in the middle of the desert — 10 m across and 25 m deep. Scuba divers come from across the world for this.

Albuquerque Historic Route 66 NeonScenic Point · Central Avenue retains the most intact collection of 1940s and 1950s neon motel and restaurant signs of any Route 66 city. The Route 66 Diner is the classic stop.

Old Town AlbuquerqueRestaurant · The 1706 Spanish colonial plaza with adobe buildings, turquoise jewelry, and New Mexican food. Order the green chile cheeseburger — New Mexico's state question is literally "red or green?"

Albuquerque, NMOvernight · Overnight in Albuquerque. The Sandia Mountains tram to 3,255 m has sunset views covering 40,000 square miles. The International Balloon Fiesta (October) is the world's largest.

DAY 07

Acoma Sky City Pueblo → Flagstaff, AZ

6 stops

Acoma Sky City PuebloScenic Point · A Native American village on top of a 110 m sandstone mesa — continuously inhabited for over 2,000 years. The oldest continuously occupied community in North America. Tours depart the cultural center below.

Gallup NM — El Rancho HotelRestaurant · The 1937 hotel that housed every major Hollywood star filming in the Southwest — John Wayne, Ronald Reagan, Katherine Hepburn, all signed the registry. Lunch in the dining room.

Petrified Forest National ParkScenic Point · Ancient logs replaced by quartz crystal over 225 million years — fragments of rainbow-colored stone scattered across a bare desert. The 48 km park road follows the original Route 66 alignment.

Painted Desert OverlookPhoto Spot · Bands of red, pink, purple, and white bentonite clay extending 50 km in every direction. The light at late afternoon turns the colours electric.

Standin' on the Corner, Winslow AZPhoto Spot · The Eagles lyric from "Take It Easy" immortalized in bronze: a man and a flatbed Ford on a Winslow corner. One of the most visited stops on the entire route.

Flagstaff, AZOvernight · Overnight in Flagstaff. Route 66 runs through the historic downtown. The Grand Canyon is 80 km north — add a morning detour. Strong craft beer scene and excellent Southwest cuisine.

DAY 08

Seligman AZ — Angel Delgadillo's → Santa Monica Pier — End of the Trail

7 stops

Seligman AZ — Angel Delgadillo'sScenic Point · Angel Delgadillo's barber shop is the spiritual start of the Route 66 preservation movement. His 1987 letter-writing campaign saved the road from oblivion. He still cuts hair at over 90 years old.

Oatman, AZScenic Point · A near-ghost town where wild burros roam the main street begging for food. The original Route 66 alignment climbs over Sitgreaves Pass — no bypass, the real switchbacks as God and the 1920s intended.

Needles, CAFuel Stop · First California city. The road enters the Mojave Desert here. Fuel up — it's hot, and the next stretch is remote. Charlie Brown named his dog Snoopy's brother after this town.

Roy's Motel and Café, Amboy CAPhoto Spot · A perfectly preserved 1938 gas station and motel in the absolute middle of the Mojave. The neon sign glowing against the desert silence is one of the great Route 66 images.

Barstow, CARestaurant · Mid-Mojave service town. The Casa del Desierto — a 1911 Fred Harvey railroad hotel — has been restored and is worth a stop. Cold drinks and a sit-down meal before the final push to the coast.

San Bernardino — Route 66 MuseumScenic Point · The original McDonald's site is here (the chain started in San Bernardino in 1940). The Route 66 Mother Road Museum in the old Santa Fe Depot tells the complete history.

Santa Monica Pier — End of the TrailEnd · The official western terminus of US Route 66. The "End of the Trail" sign hangs at the pier entrance. After 3,940 km, walk to the end of the pier and stand over the Pacific. You earned it.