Route 66 Road Trip: Chicago to Santa Monica Highlights

The route begins in downtown Chicago at the 'Begin Route 66' sign on Adams Street. The Illinois segment is the most heavily preserved and best-signed stretch on the entire route.

• Gemini Giant (Wilmington) — a 28-ft fiberglass spaceman, the most photographed roadside giant on the route
• Chain of Rocks Bridge (St. Louis border) — a 22-degree bend mid-span, now pedestrian-only

Missouri delivers the route's best cave systems and the transition from Midwest farmland into Ozark hill country.

• Gateway Arch (St. Louis) — 630 ft, the tallest arch in the world
• Meramec Caverns — the route's most famous roadside cave attraction, advertised on barn roofs for decades
• Route 66 State Park — interpretive museum in a former roadhouse

The shortest state segment on the entire route — 13 miles that take about 20 minutes to drive, and are easy to miss entirely if you follow modern interstate routing.

• Galena — the town's restored Kan-O-Tex service station inspired the character Tow Mater in Cars
• Rainbow Curve Bridge (Riverton) — the last surviving Marsh Arch bridge on Route 66

At 13 miles, Kansas is a drive-through segment — but it is the only way to say you've driven all 8 states.

Oklahoma has the longest continuous stretch of original, driveable Route 66 pavement of any state — this is where the route feels most authentic.

• Blue Whale of Catoosa — a hand-built concrete whale on a swimming hole, pure roadside Americana
• Round Barn (Arcadia) — a genuinely round 1898 barn, restored by volunteers
• POPS (Arcadia) — a 66-ft soda bottle sculpture and 700+ soda varieties

The Texas Panhandle segment is flat, fast, and anchored by the single most participatory attraction on the route.

• Cadillac Ranch (Amarillo) — 10 Cadillacs buried nose-down; bring your own spray paint, painting them is encouraged
• Midpoint Cafe (Adrian) — the geographic midpoint of Route 66, 1,139 miles in each direction

Cadillac Ranch is free, open 24 hours, and in an open field — wear shoes you don't mind getting muddy.

New Mexico offers the route's best food and the most dramatic light. Santa Fe was on the original pre-1937 alignment; the later alignment runs straight through Albuquerque.

• Blue Hole (Santa Rosa) — an 80-ft-deep artesian spring at a constant 62°F, popular with scuba divers
• Central Avenue (Albuquerque) — the longest urban neon stretch remaining on Route 66
• Tucumcari — the highest concentration of restored neon motel signage on the route

For a deeper New Mexico detour, our New Mexico road trip guide covers Santa Fe and the High Road to Taos in detail.

Arizona holds the route's longest uninterrupted original alignment and the town that saved Route 66 from being forgotten entirely.

• Petrified Forest National Park — the only national park containing a section of Route 66
• Wigwam Motel (Holbrook) — sleep in a concrete teepee, operating since 1950
• Seligman — the town whose barber launched the Route 66 preservation movement; inspired Radiator Springs in Cars
• Oatman — wild burros roam the main street of this former mining town

The final leg crosses the Mojave before dropping into the Los Angeles basin and ending at the Pacific.

• Roy's Motel and Cafe (Amboy) — the most iconic surviving neon sign in the Mojave
• Santa Monica Pier — the official 'End of the Trail' sign and the route's western terminus

The Mojave stretch between Ludlow and Barstow has the longest fuel gap on the route — fill up before entering it.