ROUTE 66 · TRIP PLAN
Route 66 in 14 days
Fourteen driving days from Chicago to Santa Monica, a town to sleep in every night, and the stories you’ll hear along the way.
- 2,290 mi Chicago to Santa Monica
- 14 overnight stops
- 50 mph planning pace
How this plan works
Each day ends in a town with its own page in this guide, so you can see what is there before you book a room. Distances are measured along the route the Lorecast app follows. It keeps to the old road in many places and to the interstate in others, so your odometer will read a little differently.
Drive times assume an average of 50 mph without stops. On the old two-lane road you will often go slower, and every museum, diner and photo stop adds time, so treat the hours as a minimum.
This plan covers the towns where Lorecast has stories we have checked. Some well-known stops are not in this guide yet, and Lorecast has no stories for Route 66’s short stretch through Kansas yet.
Day by day
- Day 1
Chicago → Springfield, Illinois
- Joliet — A station without trains, The old Joliet Post Office, The YMCA the Burnham brothers built, The Henry Mansion’s fall and revival
- Springfield — The capitol rebuilt stone by stone, Springfield’s automobile row, “Pray for me”: Lincoln’s farewell, The poet who chanted, The shoebox fortune in room 546
- On the road — Dell Rhea's Chicken Basket, Willowbrook, White Fence Farm and the coin flip, Ambler's Texaco, Dwight, The Standard Oil station in Odell, Dixie Truckers Home, McLean, The Palms Grill Cafe, Atlanta
- Day 2
- Day 3
St. Louis → Springfield, Missouri
West of St. Louis the road climbs into the Ozarks. Interstate 44 now follows much of it, and state routes carry other stretches.
- Lebanon — page coming
- Springfield — A Shrine Mosque named for a poem, Rock Fountain Court, a Route 66 tourist court, The footbridge over 13 tracks, Stone Chapel and its 1906 organ, The museum that never left private hands
- On the road — How Sullivan got its name, Rolla's bank-and-hotel building, How Devils Elbow got its name, The Old Stagecoach Stop, Waynesville
- Day 4
Springfield → Tulsa, Oklahoma
Past Joplin, Route 66 clips the southeastern corner of Kansas through Galena, Riverton and Baxter Springs. Lorecast has no stories there yet; the Missouri page says more.
- Joplin — Bonnie and Clyde's Joplin hideout, The department store that became City Hall, A depot built with mine waste, The Fox Theater, now a church, The hotel that fell a day early
- Tulsa — The bridge that brought Route 66 to Tulsa, A filling station with a tile roof, The skyscraper given to the Boy Scouts, Who designed Boston Avenue Church?, The drive-in that survived a tornado
- Day 5
Tulsa → Oklahoma City, Oklahoma
East of Oklahoma City, old Route 66 stays on its own road as a free alternative to the Turner Turnpike.
- Day 6
Oklahoma City → Amarillo, Texas
West of Oklahoma City, Interstate 40 has largely replaced the old road, which survives as business loops through El Reno, Clinton, Elk City and Sayre.
- Elk City — A Pueblo Deco station in Canute, Corn ground at any time, Sayre’s double-domed courthouse, A streamlined station in Sayre
- Amarillo — Ten Cadillacs, nose-first, The Ranchotel, a 1940 tourist court, The Herring Hotel's long wait, The Madame Queen, A 1930s federal courthouse downtown
- On the road — Lucille Hamons, Mother of the Mother Road, McLain Rogers Park, Clinton, Sayre's Rock Island depot, The West Winds Motel, Erick
- Day 7
Amarillo → Tucumcari, New Mexico
Adrian, west of Amarillo, bills itself as the geographic midpoint of Route 66. Near the New Mexico line the original road from Glenrio through Endee and Bard to San Jon is gravel.
- Day 8
Tucumcari → Albuquerque, New Mexico
Until 1937 Route 66 took a longer loop north through Santa Fe between Santa Rosa and Albuquerque. Today’s route follows the 1927 cutoff straight west.
- Santa Rosa — The Blue Hole, The runway that used to be Route 66, A 1917 Craftsman bungalow
- Albuquerque — How the KiMo got its name, Tower Court, a 1930s motor court, The La Mesa Motel, gone since 2003, The bank that used mirrors, A Venetian palace in the desert
- On the road — A glider museum on Route 66
- Day 9
Albuquerque → Gallup, New Mexico
Much of the old road survives beside Interstate 40 as state roads and frontage roads; from Grants to the Arizona line it meanders around the interstate.
- Day 10
- Day 11
Holbrook → Williams, Arizona
- Day 12
Williams → Kingman, Arizona
West of Seligman, State Route 66 leaves the interstate and arcs north through Peach Springs, Truxton, Valentine and Hackberry to Kingman, up to 16 miles from the freeway.
- Day 13
Kingman → Barstow, California
Beyond Kingman the original road climbs the Black Mountains through Oatman and over Sitgreaves Pass to Topock; a newer line through Yucca replaced it in 1952.
- Day 14
Barstow → Santa Monica, California
West of San Bernardino, Route 66 becomes city streets: Foothill Boulevard, Colorado Boulevard through Pasadena, the Arroyo Seco Parkway, then Sunset and Santa Monica boulevards.
- San Bernardino — A depot built to withstand fire, The 1927 courthouse, Where Hollywood tested its films, The 1931 post office
- Santa Monica — Where the fitness boom began, The carousel house on the pier, Saint Monica, finished by the Mount Rushmore sculptor, The Sovereign: no reticence
- On the road — Cajon Pass: a trail before the highway, La Verne’s movie wedding church, The largest bougainvillea in the country
HEAR IT ON THE ROAD
Hear the stories of all fourteen days on the road.
Lorecast plays short stories about the places around you, hands-free. Download Route 66 before you leave and it works offline. Route 66 is free through December 31, 2027.
How these stories are made
Lorecast stories are written with AI using only the sources listed under each story, and they are narrated with synthetic voices. An automatic check traces every name and date back to those sources, and legends are told as legends. If you spot a mistake, write to hello@lorecast.net.
All sources and licences
- Wikipedia: U.S. Route 66 in Missouri
- Wikipedia: U.S. Route 66 in Kansas
- Wikipedia: U.S. Route 66 in Oklahoma
- Wikipedia: U.S. Route 66 in Texas
- Wikipedia: U.S. Route 66 in New Mexico
- Wikipedia: U.S. Route 66 in Arizona
- Wikipedia: U.S. Route 66 in California
Story and page texts are original writing based on the facts in these sources. Wikipedia and Wikivoyage text is available under CC BY-SA 4.0; Wikidata under CC0; National Register of Historic Places records are public domain. Map data © OpenStreetMap contributors, ODbL. Distances are along the route as Lorecast maps it and differ slightly from other guides.
Photo credits
Updated 10 October 2026.