If you want to experience as much of the original Route 66 as possible, I’d recommend a 14-day road trip. This pace gives you time to drive surviving sections of the historic road, visit classic roadside attractions, and enjoy some of America’s most iconic small towns.
Day 1: Chicago, Illinois to Springfield, Illinois
Mileage: ~200 miles
Highlights:
- Begin at the historic Route 66 Begin Sign in downtown Chicago
- Joliet Area Historical Museum
- Gemini Giant in Wilmington
- Launching Pad Drive-In
- Route 66 Hall of Fame & Museum in Pontiac
- Lincoln sites in Springfield
Overnight: Springfield
Day 2: Springfield to St. Louis, Missouri
Mileage: ~115 miles
Highlights:
- Cozy Dog Drive-In (claims birthplace of the corn dog on a stick)
- Chain of Rocks Bridge over the Mississippi
- Explore St. Louis
- Gateway Arch
Overnight: St. Louis
Day 3: St. Louis to Springfield, Missouri
Mileage: ~220 miles
Highlights:
- Meramec Caverns
- Cuba’s Route 66 murals
- Devil’s Elbow historic bridge
- Red Oak II ghost town
- Downtown Springfield, MO
Overnight: Springfield, MO
Day 4: Springfield, Missouri to Tulsa, Oklahoma
Mileage: ~180 miles
Highlights:
- Route 66 Car Museum in Carthage
- Rainbow Bridge in Kansas
- Historic Route 66 through Miami, Oklahoma
- Blue Whale of Catoosa
- Tulsa’s Art Deco downtown
Overnight: Tulsa
Day 5: Tulsa to Oklahoma City
Mileage: ~110 miles
Highlights:
- Route 66 Museum in Clinton
- Arcadia Round Barn
- Pops 66 Soda Ranch
- Historic Bricktown district
Overnight: Oklahoma City
Day 6: Oklahoma City to Amarillo, Texas
Mileage: ~260 miles
Highlights:
- Historic Route 66 through Weatherford
- Shamrock’s restored Conoco Tower Station
- U-Drop Inn Cafe
- Cadillac Ranch at Sunset
Overnight: Amarillo
Day 7: Amarillo to Santa Fe, New Mexico
Mileage: ~290 miles
Highlights:
- MidPoint Cafe in Adrian (halfway point of Route 66)
- Tucumcari’s neon motel district
- Optional original Route 66 alignment to Santa Fe
- Plaza and galleries in Santa Fe
Overnight: Santa Fe
Day 8: Santa Fe to Albuquerque
Mileage: ~65 miles
Take a shorter day.
Highlights:
- Turquoise Trail scenic route
- Old Town Albuquerque
- Route 66 neon signs
- Indian Pueblo Cultural Center
Overnight: Albuquerque
Day 9: Albuquerque to Gallup
Mileage: ~140 miles
Highlights:
- Laguna Pueblo
- Grants mining history
- Continental Divide crossing
- Historic El Rancho Hotel in Gallup
Overnight: Gallup
Day 10: Gallup to Holbrook, Arizona
Mileage: ~95 miles
Highlights:
- Petrified Forest National Park
- Painted Desert
- Route alignment through the park
- Wigwam Motel
Overnight: Holbrook
Day 11: Holbrook to Williams, Arizona
Mileage: ~190 miles
Highlights:
- Winslow / “Standin’ on the Corner” Park
- Meteor Crater
- Flagstaff’s preserved Route 66 district
- Historic Williams
Overnight: Williams
Day 12: Grand Canyon Excursion
Mileage: ~120 miles round trip
Highlights:
- Full day at Grand Canyon National Park
- Return to Williams
Overnight: Williams
Day 13: Williams to Barstow, California
Mileage: ~360 miles
Highlights:
- Seligman (birthplace of Route 66 preservation)
- Hackberry General Store
- Kingman
- Oatman wild burros
- Mojave Desert crossing
- Barstow Route 66 Museum
Overnight: Barstow
Day 14: Barstow to Santa Monica
Mileage: ~130 miles
Highlights:
- Elmer’s Bottle Tree Ranch
- San Bernardino’s McDonald’s Museum site
- Pasadena sections of historic Route 66
- End of the famous Santa Monica Piet “End of the Trail” sign
Celebrate with sunset on the Pacific Ocean.
Don’t Miss Top 10 Route 66 Stops
- Route 66 Begin Sign, Chicago
- Chain of Rocks Bridge, Missouri
- Blue Whale of Catoosa, Oklahoma
- Cadillac Ranch, Texas
- MidPoint Cafe, Adrian, Texas
- Santa Fe Historic Plaza
- Petrified Forest National Park
- Wigwam Motel, Holbrook
- Oatman, Arizona
- Santa Monica Pier
Total distance: Approximately 2,700-3,000 miles depending on how many original alignments and side trips you include.
For a true Route 66 enthusiast, I’d also suggest adding a few extra nights in Tulsa, Santa Fe, Williams, and Oatman/Kingman, as these areas contain some of the best-preserved and most scenic sections of the original road.