Chicago → Pontiac
Launch at the eastern gateway, then collect classic Illinois architecture, diners, murals, and the first passport stamps.
Open map layer →Travel planner · 1926 → 2026
Plan the road. Keep the story.
66 Roadies turns a Chicago-to-Santa Monica drive into a living itinerary: real stops, historic lodging, passport moments, photos, and the local businesses worth pulling over for.
This is a curated starting route. Confirm availability, hours, prices, and road conditions with each business before booking or driving.
ROUTE
66
66
CHICAGOST. LOUISOKLAHOMADESERTSANTA MONICA
Stops to see
stays to remember
stories to share
stays to remember
stories to share
Sample itinerary
A five-day first pass.
Use this as the starting skeleton, then expand it with nearby food, museums, alignments, photo challenges, and the places your roadie crew recommends.
St. Louis → Cuba
Cross the river, follow the Ozarks, and give the historic motel courts enough time to tell their stories.
Plan passport stops →Carthage → Catoosa
Make room for the Boots Court, Kansas bridges, the Blue Whale, and the roadside giants that make 66 feel alive.
Save a road story →Shamrock → Gallup
Follow neon, towers, trading-country architecture, and the high-desert transitions that reward a slower drive.
Read the source trail →Holbrook → Santa Monica
End with teepees, desert neon, historic alignments, and the Pacific finish—without losing the places between them.
See the full corridor →Where to sleep
Featured lodging, not fake rankings.
We’ll show current Route 66 lodging with its source and let businesses claim or correct their listings. “Featured” means curated for the route—not a paid popularity claim.
Boots Court Motel
Carthage’s Streamline Moderne stay for roadies who want the motel itself to be part of the story.
Source lane: Visit Missouri · verify availability directClaim or sponsor this stop →Route 66 Rail Haven
A Springfield lodging anchor surfaced in Missouri’s official places-to-stay directory.
Source lane: Visit Missouri · verify availability directClaim or sponsor this stop →Historic Route 66 Guest House
A current Bristow guest house listing for travelers who want a smaller, local stay.
Source lane: TravelOK · verify availability directClaim or sponsor this stop →Put your motel here.
Own a hotel, motel, cabin, campground, or guest house? Sponsor a planning card and pair it with a reward or photo challenge.
Founding placement is labeled as sponsored and measured with aggregate activity.Request the sponsor deck →Route 66 has more than 100 itinerary sites in the National Park Service travel guide and more than 250 National Register buildings, bridges, alignments, and other sites. The planner will grow from source-backed records, owner corrections, and field verification.
For the businesses that keep 66 moving
Get pulled over for the right reason.
A Roadie sees your stop in the itinerary, saves it, checks in, scans your sign, redeems an offer, and carries the story forward. Start with a low-risk founding listing; add paid placement when the proof is useful.