OutsideMay 27, 2026
Route 66 Redux: America's Iconic Highway Is Transforming This Year As It Turns 100
For its centennial, America's most iconic highway gets a glow-up with fresh bicycle paths, revived retro hotels, and pavement that sings (for real).
29 things in this story
- Adventure Cycling AssociationPlaceExplore the world of Bicycle Travel with mapped routes and community support for unforgettable journeys and adventures.
- Bicycle Route 66TrailRoute 66, also known as the Mother Road, from Chicago, Illinois, to Santa Monica, California.
- Illinois Route 66 TrailTrail369-mile stretch of bike-friendly paths
- Mississippi RiverSightIt is the second-longest river in the United States, behind only the Missouri.
- Adventure Cycling Association’s Bicycle Route 66Trail2,493-mile cross-country trek through eight states
- Meadow Gold neon signSightIconic landmark cyclists pedal past in Tulsa
- Round BarnSightExperience The Arcadia Round Barn The Round Barn is listed on the National Register of Historic Places and is more than…
- Pops 66SightStop for a soda and selfie by 66-foot-tall bottle
- Geary’s Pony BridgeSightMade famous in the 1940 film The Grapes of Wrath
- Totem Pole ParkSightHome of the world’s largest concrete totem pole
- Santa Ana River TrailTrail3.8-mile extension of Route 66-adjacent trail
- Pacific Electric Inland Empire TrailTrail20-mile trail starting at Route 66 Trailhead Park
- Wigwam MotelHotelRetro motel known for striking architecture
- Hotel El RanchoHotelHistoric Harvey House where 1930s elite bedded down
- The BarfieldHotelNew boutique hotel in renovated 1920s skyscraper
- Palo Duro CanyonSightSecond largest canyon in the U.S.
- ARRIVE HotelHotelTransformed from Downtowner Motor Inn in 2025
- Americana Motor HotelHotelRenovated 1962 motor lodge, retro-futuristic nod
- DwellHotelGlamping destination on Arizona-California border
- U.S. Bicycle Route SystemPlaceWe're building new opportunities for cross-country travel and regional touring right from your backyard.
- Route 66’s western terminusSightEnd of the Trail kiosk at Santa Monica Pier
- Gemini GiantSight30-foot-tall 1960s space-age Muffler Man statue
- Birthplace of Route 66Sight20-foot-tall monument by Rail Haven Hotel
- The Filling StationRestaurant1950s gas station remodeled as visitor center
- Blue WhaleSightGigantic fiberglass whale with visitor center
- Road TunesSightSinging road tribute plays 'Take it Easy'
- U.S. Bicycle Route System (USBRS)Place
- Route 66 Trailhead ParkSight
- Rail Haven HotelHotel
