14 Day Route 66 Road Trip Itinerary
Route 66 is a journey defined by moments rather than milestones. Slowing the trip to fourteen days allows travelers to experience the road as it was intended, unhurried, curious, and full of character. This itinerary is designed to help visitors feel the rhythm of the Mother Road while still offering structure and clarity for daily planning.
Starting in the Midwest and ending at the Pacific Ocean, this route blends classic Americana, wide open landscapes, and small towns where Route 66 still feels alive.
Route 66 Road Trip Map
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Overview
This 14 day Route 66 road trip itinerary travels from Chicago to Santa Monica, crossing eight states and nearly 2,400 miles. Each day is paced to balance driving time with exploration, giving travelers the flexibility to linger without feeling behind schedule.
The route highlights the gradual transformation of scenery, from farmland and rolling hills to desert highways and coastal views, while keeping the focus on the journey itself.
Day 1: Chicago to Pontiac Illinois
The first day eases travelers into Route 66, transitioning from busy city streets into quieter Midwestern roads. This stretch introduces early Route 66 towns, historic alignments, and the nostalgic roadside feel that defines the journey ahead.
Things to see and do along the way:
• Stop at the official Route 66 starting point
• Drive through early Route 66 towns like Joliet and Wilmington
• Visit classic diners and preserved gas stations
• Explore Route 66 murals and small museums in Pontiac
Where to stay: Pontiac Illinois
Day 2: Pontiac Illinois to Springfield Illinois
This day showcases some of the best preserved Route 66 scenery in Illinois. The road feels relaxed and nostalgic, with original pavement and towns that have changed little over time.
Things to see and do along the way:
• Drive historic stretches of original Route 66
• Stop in small towns with vintage signage
• Explore roadside attractions unique to Illinois
• Spend time in Springfield’s historic downtown
Where to stay: Springfield Illinois
Day 3: Springfield Illinois to St. Louis Missouri
The drive gradually leads toward the Mississippi River, creating a sense of anticipation as the route moves west. This day blends rural scenery with the energy of a major river city.
Things to see and do along the way:
• Enjoy scenic farmland drives through central Illinois
• Stop at classic roadside attractions
• Cross the Mississippi River into Missouri
• Explore historic neighborhoods and riverfront areas
Where to stay: St. Louis Missouri
Day 4: St. Louis Missouri to Cuba Missouri
Rather than pushing deep into the state, this shorter day focuses on Missouri’s scenic and historic side. Rolling hills and forests replace flat farmland, offering a very different driving experience.
Things to see and do along the way:
• Drive winding stretches of Route 66 through wooded landscapes
• Visit historic bridges and original road segments
• Stop in mural filled Route 66 towns
• Relax and explore Cuba’s Route 66 identity
Where to stay: Cuba Missouri
Day 5: Cuba Missouri to Springfield Missouri
This stretch continues through classic Missouri Route 66 towns, offering a slower pace and frequent opportunities to stop, explore, and photograph roadside landmarks.
Things to see and do along the way
• Visit classic diners and roadside cafes
• Explore restored service stations and motels
• Enjoy scenic backroad driving
• Walk Springfield Missouri’s historic areas
Where to stay: Springfield Missouri
Day 6: Springfield Missouri to Tulsa Oklahoma
As the road heads southwest, the landscape opens up and driving days begin to feel longer and more expansive. This day marks a shift toward wide skies and longer horizons.
Things to see and do along the way
• Pass briefly through Kansas on Route 66
• Explore preserved roadside attractions in Oklahoma
• Stop in small towns celebrating Route 66 culture
• Explore Tulsa’s historic districts
Where to stay: Tulsa Oklahoma
Day 7: Tulsa Oklahoma to Oklahoma City Oklahoma
This is a shorter driving day designed to allow deeper exploration of Oklahoma’s Route 66 heritage. The road feels especially rich with classic motels, neon signs, and historic stops.
Things to see and do along the way:
• Visit Route 66 museums and landmarks
• Drive long open highway stretches
• Stop in neon lit Route 66 towns
• Explore historic neighborhoods in Oklahoma City
Where to stay: Oklahoma City Oklahoma
Day 8: Oklahoma City Oklahoma to Amarillo Texas
The drive becomes flatter and more expansive as the route enters the Texas Panhandle. Big skies and classic road trip scenery dominate the day.
Things to see and do along the way:
• Stop at roadside attractions across western Oklahoma
• Enjoy long uninterrupted highway drives
• Cross into Texas
• Experience Amarillo’s Route 66 atmosphere
Where to stay: Amarillo Texas
Day 9: Amarillo Texas to Tucumcari New Mexico
This day introduces the Southwest, with noticeable changes in color, elevation, and atmosphere. Neon signs and classic motels begin to appear more frequently.
Things to see and do along the way:
• Drive through classic Route 66 towns in Texas
• Cross into New Mexico
• Photograph vintage neon signage
• Explore Tucumcari’s Route 66 corridor
Where to stay: Tucumcari New Mexico
Day 10: Tucumcari New Mexico to Santa Fe New Mexico
The road climbs into higher elevations, bringing cooler temperatures and a shift in scenery. This day adds cultural depth to the journey.
Things to see and do along the way
• Drive scenic high plains landscapes
• Stop in small New Mexico towns
• Detour toward Santa Fe
• Explore historic streets and plazas
Where to stay: Santa Fe New Mexico
Day 11: Santa Fe New Mexico to Gallup New Mexico
This stretch delivers dramatic landscapes and a strong sense of Route 66 history. Wide mesas and open skies define much of the drive.
Things to see and do along the way:
• Drive through red rock and desert scenery
• Stop at trading posts and roadside stands
• Enjoy quiet highway segments
• Explore Gallup’s Route 66 heritage
Where to stay: Gallup New Mexico
Day 12: Gallup New Mexico to Flagstaff Arizona
Crossing into Arizona brings cooler temperatures and forested landscapes. The scenery changes quickly, offering a refreshing contrast to desert stretches. Flaggstaff is an amazing city and nature escape as a whole.
Things to see and do along the way:
• Drive through desert and high elevation terrain
• Stop at scenic viewpoints, if you have time, see Palo Duro Canyon State Park
• Explore Flagstaff’s walkable downtown
• Enjoy mountain town vibes
Where to stay: Flagstaff Arizona
Day 13: Flagstaff Arizona to Kingman Arizona
This day features some of the most iconic Route 66 driving in the entire country. Long desert roads and preserved towns define the experience.
Things to see and do along the way:
• Drive classic desert Route 66 stretches
• Explore preserved roadside towns
• Stop at scenic overlooks
• Experience Kingman’s Route 66 culture
Where to stay: Kingman Arizona
Day 14: Kingman Arizona to Santa Monica California
The final day delivers a dramatic transition from desert landscapes to the Pacific coastline. At Santa Monica, traffic increases and scenery softens as the journey reaches its emotional conclusion.
Things to see and do along the way:
• Drive through the Mojave Desert
• Experience the gradual return of urban landscapes
• Follow Route 66 to its western endpoint
• Walk the pier and enjoy ocean views
Where to stay: Santa Monica California
Related
Final Thoughts
This 14 day Route 66 road trip itinerary is built for travelers who want to experience the road fully rather than rush through it. Each day offers structure while leaving room for spontaneity, discovery, and rest.
Route 66 rewards those who slow down, stay curious, and embrace the unexpected. With two full weeks on the road, travelers gain the freedom to experience the Mother Road in a way that feels meaningful, memorable, and uniquely their own.
