A morning somewhere on Route 66
When Jess from our BugBitten team rolled out of a Springfield, Illinois motel at half past six on a Tuesday, the sun had barely cleared the tree line and the diner across the road was already doing a brisk trade in eggs and filter coffee. She'd been on the road for nine days by that point, legs finding their rhythm, handlebar bag stuffed with sunscreen, a dog-eared paper map, and a bag of trail mix that had seen better days. The motel owner — a bloke in his seventies who'd run the place since 1987 — had left a handwritten note under her door: Watch the trucks on the bend past Litchfield. She still thinks about that note. Not because the bend was particularly hairy, but because it captured something essential about this route: people along it have been watching out for travellers for nearly a hundred years, and the habit hasn't worn off yet.
That's the thing about riding Route 66 by bicycle. You don't experience it the way a car driver does — a blurred ribbon of asphalt between podcasts. You're in it. You smell the wet tarmac after a Missouri thunderstorm. You hear the grain elevator fans going at full noise on a still afternoon outside Elk City. You feel the exact moment the road surface changes beneath your tyres when you cross from one state into the next. Four thousand kilometres sounds like an abstraction until you're somewhere in the middle of the Mojave with a tailwind finally — finally — pushing you west and the light going copper-gold across the Joshua trees, and you think: right, this is what it's actually about.
This is not a route for someone looking for a gentle cycle path. There are no separated lanes, no conveniently placed bike infrastructure, no on-road signage designed with cyclists in mind. What there is, though, is one of the most storied and genuinely varied overland routes in the world, and doing it under your own power gives you access to a version of it that no other traveller gets.
What makes this route worth your time
Let's be direct: Route 66 gets a lot of tourist attention, and some of that attention has produced a version of the road that can feel curated and slightly theme-parked. The giant fibreglass statues, the neon-sign restoration projects, the retro diners with laminated menus — some of it is great, some of it is kitsch, and from a car window it's easy to mistake one for the other. On a bicycle, you don't have that problem, because you're moving slowly enough that the real thing keeps revealing itself between the landmarks.
The route covers eight states — Illinois, Missouri, Kansas (just a sliver), Oklahoma, Texas, New Mexico, Arizona, and California — and each one delivers a noticeably different landscape, climate, road character, and population. Illinois is flat farmland and mid-sized towns with good bakeries. Missouri brings the Ozarks, proper hills, and creek crossings on bridges old enough to make you wonder about load ratings. Oklahoma has a particular wide-sky quality — not desert, not prairie exactly, but something in between that makes you feel exposed and alert. New Mexico shifts into high desert country, all mesa and red rock. Arizona gives you Painted Desert and Petrified Forest. California delivers the Mojave and then, eventually, the Pacific.
For cyclists who've already done the Southern Tier Route and are looking for something that offers more historical texture and town-to-town variety, Route 66 is a natural next step. It's longer, more varied, and carries more cultural weight per kilometre than almost any other route in North America.
The road surface is genuinely mixed. Illinois and Missouri are generally smooth. Oklahoma has patchy stretches. New Mexico and the Mojave are where you'll encounter cracked, buckled, or occasionally absent original alignment — some sections revert to gravel without much warning. Tubeless tyres or at minimum a generous supply of inner tubes is strongly advised.
How the corridor feels to ride
There's a texture to this route that's difficult to quantify but very easy to feel. The motels that line Route 66 — particularly through Oklahoma and the Texas panhandle — are not chain properties with standardised room layouts and loyalty points. They are places with personality, sometimes charming, occasionally rough around the edges, and occasionally both at once. Owners remember cyclists. If you stop somewhere and introduce yourself as a through-rider, you will almost always get a story in return — about another cyclist who came through last spring, or about the road before the interstate bypass pulled traffic away in the 1970s.
That bypass is, in fact, one of the defining features of the route's atmosphere. When Interstate 40 was built parallel to much of the old alignment, it didn't just reroute traffic — it froze sections of Route 66 in something close to the moment the cars stopped coming. Towns that lost their through-traffic never quite rebuilt themselves around anything else. Some became genuinely desolate: a boarded diner, a collapsed motel, a rusted petrol pump slowly returning to the landscape. Others maintained just enough tourism interest to keep going. A few have genuinely thrived on the nostalgia economy. Riding through this range of outcomes over forty-odd days gives you an oddly clear picture of how infrastructure shapes a community's fate.
The cycling itself across this section is moderately demanding rather than technically challenging. The Ozarks in Missouri require actual climbing fitness — sustained grades, switchbacks, and the kind of descents where you want your brakes properly set up before you start. The desert sections from eastern New Mexico through to the Californian border are a different kind of hard: relentlessly flat or gently rolling, but with heat, headwind, and serious distances between water sources. It's the kind of effort that doesn't feel hard until it does, all at once, and usually around the third hour of a four-hour push to the next town.
What to actually do here
Plan your daily kilometres honestly
Most cyclists doing this route as a through-ride settle on 90 to 120 kilometres per day with deliberate rest days factored in — one every five to seven days depending on how the legs feel. Going harder than that in the early states means arriving in the desert sections already fatigued, which is a situation you want to avoid. The flat-to-rolling terrain of Illinois and Missouri is tempting for high mileage days. Resist the urge to overcook the early section.
Eat the food
This is not advice to eat in every tourist diner — some of them are fine but unremarkable. The advice is to eat locally and eat often. The pie culture in Oklahoma is real and it is good. The green chile situation in New Mexico is something that people become genuinely evangelical about, and after a week of riding through high desert it will feel like it was put there specifically for you. Texas chicken-fried steak is a caloric event worth planning around. These are not tourist traps; they are regional food cultures that have been developing independently of one another for decades.
Use the museums selectively
Route 66 has more roadside museums per kilometre than almost any other road in America. Most of them are small, local, and staffed by volunteers with deep knowledge and a genuine desire to talk to you. The National Route 66 Museum in Elk City, Oklahoma, is a legitimate stop — several buildings covering road culture, transport history, and regional life in detail that rewards an hour or two. Pick three or four of these across the trip rather than trying to stop at every interpretive centre; otherwise they start to blur together.
Photograph the infrastructure
The bridges, in particular. Route 66 crosses dozens of historic bridges — many of them single-lane or double-arch structures from the 1920s and 1930s — and they represent a specific moment in American civil engineering history that hasn't been replicated anywhere since. The Chain of Rocks Bridge near St. Louis is one example, but it's far from the only one worth documenting.
If you're interested in the broader context of how built landscapes receive heritage recognition, the UNESCO World Heritage Centre provides a useful reference for understanding what qualifies historic routes and corridors for international significance — Route 66 has been through several nomination discussions, and understanding the criteria gives you a new lens for what you're riding through.
When to go (and when not to)
April through early June is the most consistent window for a Chicago-to-LA ride. Temperatures in Illinois and Missouri are comfortable, wildflowers are up across the plains states, and the desert sections haven't yet reached their punishing summer heights. New Mexico in May can still be cold at altitude — overnight temperatures below zero on some high-desert stretches — so a light down layer is worth carrying regardless of the overall weather forecast.
September through October works well for the same reasons in reverse: the desert has cooled from its summer peak, the light is extraordinary through autumn, and motel prices drop slightly outside the peak tourist months.
July and August through New Mexico, Arizona, and the Mojave are genuinely dangerous for unsupported cyclists. Daytime temperatures regularly exceed 40 degrees Celsius in the Mojave, and the combination of radiant heat off dark tarmac, direct sun, and low humidity removes fluid from your body faster than you can replace it without careful management. If your dates mean a summer desert crossing, plan night riding, long midday breaks, and aggressive water carrying. Carry more than you think you need.
Riding east to west — Chicago to LA — means riding against the prevailing wind for much of the desert section, which is the standard direction most cyclists choose for the narrative payoff of finishing at the Pacific. Some riders flip the route for more favourable winds; you sacrifice the ending for easier desert days. It's a genuine trade-off and worth thinking about before you commit.
How to get there and nearby stops
Getting to Chicago is straightforward from most international hubs — O'Hare and Midway are both well-served. The traditional start is at the intersection of Adams Street and Michigan Avenue in the Loop, where a sign marks the official eastern terminus. From there, following the US 66 shield signs (with the assistance of a dedicated route map — the Adventure Cycling Association produces the best available version) takes you southwest out of the city and into Illinois proper within the first day.
At the western end, Santa Monica Pier is the ceremonial finish, though the official western terminus marker is on Santa Monica Boulevard. Either way, when you get there, take the time to sit with it. Forty-odd days of pedalling from Lake Michigan to the Pacific is worth more than a quick selfie and a ride to the airport.
If you're researching other Pacific-adjacent routes in the USA, the BugBitten guide to more places in Chicago to LA covers complementary activities and routes across this corridor. And if you're considering a coastal alternative with different terrain and infrastructure, the Florida (Intercoastal Waterway) represents a contrast worth comparing — flatter, more water-adjacent, and with very different logistical demands.
For those interested in the heritage context of what they're riding through, the UNESCO World Heritage List is worth consulting — several of the geological formations and cultural sites adjacent to Route 66 in Arizona and New Mexico carry significant international heritage recognition.
Bike hire along Route 66 is not a reliable option. There is no coherent hire network along the corridor. Bring your own touring rig — a steel or titanium frame with rack and pannier mounts, wide tyres, and confidence in your own basic mechanical knowledge — or ship a bike to Chicago ahead of your arrival. The latter is manageable through several bike-shipping services and usually cheaper than you'd expect.
The not-so-good bits
Let's be honest about the downsides, because there are real ones.
Traffic is constant and unmanaged. There is no cycling infrastructure on Route 66. You share the road with trucks, caravans, motorcycles, and tourists in hire cars. The road shoulder varies from genuinely generous to nearly nonexistent, often within a few kilometres of each other. Confident road cycling skills — including the ability to hold a line at speed with a fully loaded bike — are a genuine prerequisite, not optional extra.
Water planning in the desert is serious business. Between some towns in eastern New Mexico and across portions of Arizona, water sources are 80-plus kilometres apart. Carrying three litres minimum at all times is the standard advice; carrying five is smarter if you're unsure of the next source. This is not melodrama — a mechanical breakdown in 38-degree heat, 60 kilometres from the nearest town, with one litre of water remaining, is a real emergency.
The tourist infrastructure can be oddly sparse for cyclists. Paradoxically, one of America's most famous tourist roads is not set up for cycle touring. Bike shops are rare once you leave the major cities. When you find one, buy anything you might need. Stocking up on spares — cables, tubes, brake pads, a spare derailleur hanger — in Chicago before you leave is strongly recommended.
Some stretches are genuinely dull. Parts of the Texas panhandle in particular are flat, exposed, windy, and visually monotonous for long enough that it can affect morale. These are the sections where having a podcast downloaded, a solid playlist, or a good riding companion makes a material difference.
Wild camping is variable by state. It's broadly feasible across New Mexico and Arizona with care and judgement about land access. Oklahoma and Texas are patchier — a mix of private land, no-trespassing signage, and the occasional welcoming farmer. Illinois and Missouri favour motel stops, which are plentiful and reasonably priced by international standards.
Final word from the BugBitten team
Route 66 by bicycle is a proper undertaking — not because it demands elite fitness or technical cycling ability, but because it asks you to commit six weeks of your life to one road and trust that the road will give something back. It does. Not in the form of dramatic scenery or extreme challenge, though both appear in portions. It gives back in the form of accumulated experience: forty-something days of small towns, changing landscapes, physical effort, and the particular kind of clarity that comes from moving slowly enough through a place that you actually have to reckon with it.
The BugBitten team thinks this route is worth doing at least once, and worth doing properly — meaning a well-maintained touring bike, realistic daily targets, honest preparation for the desert section, and enough flexibility in the schedule to stop when something warrants stopping. That diner with the handwritten pie board. That bridge from 1926. That conversation with the motel owner who's seen every kind of traveller the road has produced.
Go west.