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Drive Route 66 from Chicago to Santa Monica

You start in Chicago traffic, cabs leaning on their horns, and by day four you're the only car on a two-lane road in Oklahoma with grass growing through the centreline. That's the actual shape of Route 66 now: not a highway but a rumour of one, decommissioned since 1985 and kept alive in pieces by whoever bothered to repaint the shields. Two thousand four hundred and forty-eight miles end to end, and no two people drive the same version of it, because half the original road is gone or buried under the interstate that replaced it. What stays with you isn't the distance. It's the gap between what the road promises and what's actually left standing.

Practical

Cost
$1,500–4,000
Best time
Spring or autumn, avoiding northern winter closures and desert summer heat
Difficulty
Moderate
Time it takes
10-14 days at a comfortable pace
What people get wrong
People try to drive it in a week and end up doing 400-mile days that erase any point of going slow; others assume the old road is continuous and get stuck when it vanishes into an interstate on-ramp with no signage explaining where it picked back up.
With
A group

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