Route 66 at 100: Seven Days on the Mother Road

Day one is the only day you don’t drive — and it matters, because tomorrow the odometer starts moving and doesn’t stop for a week. Route 66 begins at the corner of Adams Street and Michigan Avenue, on the edge of Grant Park, where a brown “Historic Illinois Route 66 Begins” sign marks mile zero. Go at 8 AM: the light is good, the crowds aren’t there yet, and the photo — the two of you, the sign, the city behind — is the one you’ll print.

Morning: the Begin sign + Lou Mitchell’s

Walk 10 minutes west to Lou Mitchell’s (565 W Jackson, serving since 1929) — the Route 66 breakfast institution where the waitstaff still hands out free donut holes and the coffee never stops. Arrive before 9 AM; the line stretches down Jackson by 10. Order the egg skillet and split a Belgian waffle — you’ll need the fuel.

Afternoon: the river

The architecture river cruise (First Lady Cruises, departs the Riverwalk at Michigan Avenue, ~90 minutes) is the single best orientation to Chicago — a docent narrates 50+ buildings while the boat threads the canyon of towers. Book the 1 or 2 PM sailing; morning fog can mute the skyline. Check the operator’s site for current fares and buy ahead in summer — boats sell out. Rainy alternative: the Art Institute (111 S Michigan), a 10-minute walk from the river.

Evening: deep dish

Your last big-city dinner for a week. Lou Malnati’s (the Buttercrust) or Giordano’s (the classic stuffed) — both need no reservation but the pie takes 45 minutes to bake, so order the moment you sit. One medium deep dish feeds two easily. After: a Riverwalk stroll — the city lit up, the bridges, the whole trip ahead of you.

Where to stay

River North keeps you walking distance to everything. The Blackstone (historic 1929 grande dame on Michigan Ave, $200–$300) or the Godfrey (rooftop lounge, $180–$260). Budget move: the HI Chicago hostel (private rooms from ~$120). Pick up the rental car tonight if your agency allows after-hours pickup — morning traffic on I-55 costs an hour you’d rather spend at the Arch.

Bad-weather plan

The Art Institute absorbs a full rainy afternoon. The Chicago Theatre marquee tour and a Garrett Popcorn run (the cheese-and-caramel mix) cover the gaps.

Begin sign: Adams St & Michigan Ave · Lou Mitchell’s: 565 W Jackson, from 1929 · River cruise: ~90 min, book ahead · Deep dish: order on arrival, 45-min bake

The first driving day: Chicago to St. Louis, ~300 miles, about 5 hours on I-55 — the old 66 parallels the interstate most of the way, so you’re driving the corridor even on the fast road. Roll out by 8 AM to beat Chicago traffic and reach the Arch by early afternoon. Fuel up before Springfield, Illinois — the stretches south of it are long and rural, and the Lincoln sites there make a good 30-minute leg-stretcher if you want one.

Midday: the Gateway Arch

Book the tram ride in advance at gatewayarch.com — $13–$19 per person, timed entry, and it sells out on weekends. The ride is 45–60 minutes (4 minutes up in a 5-person pod, ~10 minutes at the top, 3 minutes down). The pods are tiny and windowless — cozy for two, rough if you’re claustrophobic; there’s a replica pod at the ticketing counter to try first. The grounds and the museum are free; the visitor center runs 9 AM–6 PM, last tram about an hour before close. Park at the Stadium East Garage (200 S Broadway) — about $9 for five hours with validation at the Arch.

Afternoon: the City Museum

A 10-minute drive west: the City Museum is a 10-story former shoe factory turned into the world’s greatest adult playground — slides, caves, a rooftop Ferris wheel, all built from reclaimed industrial parts. Allow 2–3 hours; wear clothes you can crawl in and closed-toe shoes. Check the museum’s site for current admission — it’s a paid ticket and worth every cent. Quieter alternative: the Old Courthouse (free, 9 AM–5 PM), where Dred Scott sued for his freedom.

Evening: burnt ends

Dinner at Pappy’s Smokehouse (3106 Olive St) — the burnt ends sell out nightly, so go before 6 PM or accept the ribs (no hardship). Then walk the Mississippi riverfront at dusk — the Arch lit up, the barges, the whole river doing its slow work. This is the trip’s first unhurried window; take it.

Where to stay

Downtown, near the Arch — you’ll walk to dinner and the riverfront. Drury Plaza St. Louis at the Arch (free evening snacks, $170–$240) or the Hilton at the Ballpark for the stadium view. Both put Day 3’s westward start 10 minutes away.

Bad-weather plan

The City Museum is almost entirely indoors — it’s the perfect rain plan. The Missouri History Museum in Forest Park (free) covers the 1904 World’s Fair and the Arch’s construction.

Chicago to St. Louis: ~300 mi, 5 hr via I-55 · Arch tram: $13–$19, book timed tickets · Visitor center: 9 AM–6 PM · Pappy’s: go before 6 PM for burnt ends

The long day: St. Louis to Tulsa, ~400 miles, 6–7 hours of driving plus stops. This is the day the trip earns its road-trip credentials — the Ozarks roll under the wheels, the roadside giants start appearing, and you cross three states before dinner. Split the driving: swap at Springfield, Missouri (the halfway point and the birthplace of Route 66, named in a 1926 telegram). Keep the tank above half — the I-44 stretches are well-served but the old-66 detours aren’t.

Morning: Cuba and the giants

Take the old 66 alignment through Cuba, Missouri — the town’s outdoor murals tell the road’s story wall by wall, and the Wagon Wheel Motel (1938) is the oldest continuously operating motel on 66. Ten minutes west in Fanning: the World’s Largest Rocking Chair — 42 feet tall, free, and the photo takes 5 minutes. It’s gloriously silly; that’s the point.

Midday: caverns or fudge

Two options, pick one. Meramec Caverns (45 minutes west of St. Louis off I-44) runs 1.5-hour guided tours through rooms Jesse James supposedly hid in — check the caverns’ site for current admission; the cave is a constant 58°F, so bring a layer even in summer. Or push on to Uranus Fudge Factory in St. Robert — fudge, a sideshow museum, and the best bathroom break on this stretch. Either way, lunch in Springfield: Cashew Station or the Route 66-themed diners on College Street.

Afternoon: Kansas in 13 miles

Route 66 clips just 13.2 miles of Kansas — and it packs them in. Galena’s Cars on the Route is the old Kan-O-Tex service station where a rusty tow truck inspired Mater in Cars; the owners will tell you the whole story if you ask. Then into Oklahoma, where the road gets wide and the sky gets bigger.

Evening: the Blue Whale

The Blue Whale of Catoosa — a 20-foot concrete whale built as an anniversary surprise in 1972, now the road’s most beloved swimming-hole-that-isn’t. Free, daylight hours; arrive before 6 PM for the light. Then 30 minutes into Tulsa for dinner in the Blue Dome District — Dilly Diner (in a 1940s gas station) or Elote for street-corn everything.

Where to stay

Tulsa — you’ve earned a real bed. The Campbell Hotel (a restored 1927 building, $150–$200) or the Mayo Hotel (downtown historic, rooftop bar). Both are on the old 66 corridor through town.

Bad-weather plan

Meramec Caverns is underground and weatherproof — if storms are coming, do the cave. In Tulsa, the Philbrook Museum (art in an Italian villa) absorbs a rainy evening.

St. Louis to Tulsa: ~400 mi, 6–7 hr · Split driving at Springfield, MO · Blue Whale: free, daylight · Meramec Caverns: 58°F year-round, bring a layer

Tulsa to Amarillo, ~370 miles, about 6 hours — with the day’s emotional center in the middle and its visual climax at the end. This is the day the trip gets serious and then gets silly, in that order, and the order matters. Leave Tulsa by 8:30 AM so Oklahoma City gets the morning and the Ranch gets the golden hour.

Morning: Tulsa’s deco

Before you leave, walk the Deco District: the Philcade (1929, terra-cotta lobby), Boston Avenue Methodist Church (a 225-foot art-deco tower that looks launched, not built), and the Mayo Hotel lobby. Breakfast at the Mother Road Market (11th & Lewis) — a food hall in a 1950s grocery with 20+ kitchens; the breakfast burritos are the move. 45 minutes is enough; the road is waiting.

Midday: the Oklahoma City National Memorial

Two hours west on I-40. The Oklahoma City National Memorial & Museum (620 N Harvey Ave) is the day’s serious stop — and it’s essential. Museum: $18 adult, Mon–Sat 9 AM–5 PM, Sun 12–5 PM; the outdoor memorial is free and open 24/7. Allow 2 hours for the museum; it’s emotionally heavy — the survivor stories, the children’s area — so pace yourselves and don’t schedule anything right after. The Field of 168 Empty Chairs at dusk, if your timing allows, is unforgettable. Free parking in the memorial garage with admission.

Afternoon: west on I-40

From OKC it’s 260 miles, 4 hours to Amarillo — flat, fast, and meditative. Fuel in Elk City or Sayre; the Texas panhandle stretches are empty. The Bricktown Canal in OKC makes a good leg-stretcher if you skipped it at lunch — 20 minutes, water taxis, done.

Evening: Cadillac Ranch at golden hour

Ten Cadillacs, nose-down in a wheat field since 1974, layered in fifty years of spray paint — and it’s free, open 24/7, at I-40 Exit 60 on the south frontage road. Buy spray paint in Amarillo first (any hardware store) — adding your mark is the whole ritual. Go at sunset: the light turns the paint layers cinematic, the crowds thin, and the West Texas sky does the rest. Wear shoes you don’t love — the field is mud, clay, or both. Then dinner at The Big Texan (7701 I-40, since 1960): the free 72-ounce steak challenge (steak, shrimp cocktail, baked potato, salad, and roll in under an hour) is theater; the regular steaks are the dinner. Open daily 10 AM–10:30 PM.

Where to stay

Amarillo — on the old 66 corridor for the neon. The Barfield (downtown boutique, $180–$250) or a Route 66 motor court on 6th Avenue for half that. You’re rolling early tomorrow; pick the one with the easiest parking.

Bad-weather plan

The Memorial museum is indoors and absorbing. In Amarillo, the American Quarter Horse Hall of Fame and the Big Texan’s brewery cover a stormy evening.

Tulsa to Amarillo: ~370 mi, 6 hr · OKC Memorial: $18, Mon–Sat 9–5, Sun 12–5 · Cadillac Ranch: free, 24/7, I-40 Exit 60 · Big Texan: daily 10 AM–10:30 PM

Amarillo to Albuquerque, ~290 miles, 4.5 hours — the shortest driving day, and the most neon per mile. This is the day the trip shifts from Texas flat to high desert, from roadside giants to glowing signs. Leave by 9 AM; the afternoon is for Tucumcari, and the evening belongs to Central Avenue after dark.

Morning: the Midpoint

Adrian, Texas — population ~150 — holds the Midpoint Café, marking 1,139 miles to Chicago and 1,139 to Santa Monica: exactly half the Mother Road. The café’s “ugly crust” pie is the order; the photo with the midpoint sign is mandatory. 30 minutes, then back on the road — the Texas panhandle gives way to New Mexico mesas fast.

Midday: Tucumcari

Tucumcari is the neon capital of the route — and the Blue Swallow Motel (815 E Route 66 Blvd, since 1939, on the National Register) is its crown jewel. Even if you’re not sleeping here, stop for the sign — the swallow, the shell motifs, the “100% refrigerated air” promise. Rooms run from ~$120 and the motel sells out in the centennial year, so if you want the full night-under-neon experience, book it now and plan the day around it. Lunch: Del’s Restaurant (a Tucumcari institution) or the Midpoint’s pie holding you to dinner. The Tee Pee Curios shop next door is the souvenir stop.

Afternoon: into Albuquerque

172 miles, under 3 hours on I-40. Coming into Albuquerque on Central Avenue — the old 66 alignment — you’ll pass 18 miles of restored neon: the El Vado, the Monterey, the De Anza. Check into your motel, then come back after dark — this cruise is a night drive, windows down.

Evening: Old Town

Old Town Plaza — settled 1706, anchored by San Felipe de Neri Church (1793) — is all adobe, galleries, and luminarias-in-waiting. Dinner: El Pinto (New Mexican, the green chile everything) or the Frontier Restaurant near UNM (a local institution, open late, the Frontier sweet roll is famous). Then the Central Avenue neon cruise — the trip’s most romantic hour, and it costs nothing but gas.

Where to stay

Albuquerque — on Central for the neon. The Monterey Motel (a 1950s motor court, restored, neon out front) or Hotel Andaluz (downtown historic, $170–$240). If you scored the Blue Swallow, tonight’s the night — it’s 115 miles behind you, so this is the either/or decision.

Bad-weather plan

The New Mexico Route 66 Museum in Tucumcari and Albuquerque’s Old Town galleries are the indoor backups. The neon cruise works in any weather — rain makes the signs glow harder.

Amarillo to Albuquerque: ~290 mi, 4.5 hr · Midpoint Café: 1,139 mi each way · Blue Swallow: from ~$120, books out · Central Ave: 18 mi of neon, best after dark

Albuquerque to Flagstaff, ~310 miles, 5 hours — plus the national park in the middle. This is the day the landscape does the talking: the road climbs into the high desert, the ground turns to rainbow badlands, and you sleep in a mountain town at 7,000 feet. Leave by 8 AM — the park deserves the morning light, and the afternoon is for the road.

Morning: the long empty

Fill up in Gallup — from there it’s long, empty, beautiful miles to the park. The road crosses the Continental Divide (unmarked, but you’ll feel the climb), and the mesas start doing strange things with the light. Keep water in the car; services are thin between Gallup and Holbrook.

Midday: Petrified Forest National Park

Enter at the north (I-40 Exit 311) and drive the 28-mile scenic road south — the park is designed as a one-way descent through deep time. $25 per vehicle (7-day pass), open 8 AM–5 PM daily (closed Thanksgiving and Christmas), no timed entry. The stops that matter: the Painted Desert Inn (a 1930s adobe with Fred Kabotie murals and the best overlook), Blue Mesa (a 1-mile loop through blue-and-purple badlands), Crystal Forest (a 0.75-mile paved loop among the biggest petrified logs), and the Rainbow Forest Museum at the south end. Allow 3–4 hours. Do not take wood — it’s a federal crime and the rangers mean it. Restrooms and water at both visitor centers; no food in the park beyond snack bars, so pack lunch.

Afternoon: teepees

Holbrook, 25 minutes west: the Wigwam Motel — concrete teepees, vintage cars out front, rooms ~$120. Even if you’re not sleeping in one, stop for the photo — it’s the road’s most photographed motel after the Swallow. Then 84 miles to Flagstaff on I-40, climbing into the pines.

Evening: Flagstaff

Downtown Flagstaff is the mountain-town reward: Mother Road Brewing Co. (the name is the point) for a pint, then dinner on San Francisco Street — Brix (seasonal, book ahead) or MartAnne’s Burrito Palace (a local legend, cash-friendly). At 7,000 feet, the evening is 20 degrees cooler than the desert you drove through — bring the fleece.

Where to stay

Flagstaff — downtown for the walkability. Hotel Monte Vista (1927, neon sign, reportedly haunted, $140–$200) or Little America (pines, pool, $160–$220). The Monte Vista is the Route 66 pick; Little America is the quiet one.

Bad-weather plan

The park’s museums and the Painted Desert Inn cover a dusty or drizzly visit — the overlooks are all drive-up. In Flagstaff, the Museum of Northern Arizona and the downtown breweries absorb an evening.

Albuquerque to Flagstaff: ~310 mi, 5 hr · Petrified Forest: $25/vehicle, 8 AM–5 PM daily · 28-mi scenic drive, north to south · Flagstaff: 7,000 ft — bring a layer

Flagstaff to Santa Monica, ~465 miles, 7 hours — the longest day on paper and the fastest-feeling, because every mile is the last of something. The desert gives way to the Mojave, the Mojave gives way to the sprawl, and then — suddenly, impossibly — the ocean. Leave by 7:30 AM. The Pier at sunset is non-negotiable, and LA traffic is the final boss.

Morning: Seligman

Seligman is where the modern 66 revival started — barber Angel Delgadillo (the “guardian angel of Route 66”) led the fight to sign the historic route in 1987. His barber shop is a museum of the road; across the street, brother Juan’s Snow Cap Drive-In (1953) serves burgers with a side of vaudeville — the “dead chicken” on the menu is a joke, the malts are real. 45 minutes, cash-friendly, wonderful.

Midday: Kingman

Hackberry General Store — a 1957 Corvette and a wall of vintage signs out front — then Kingman: a malt at Mr. D’z Route 66 Diner (chrome, jukebox, the real thing) and the Route 66 Museum in the Powerhouse Visitor Center if you want the full history in one room. Fuel up in Kingman — it’s the last cheap gas before California.

Afternoon: the long push

Oatman is the optional detour — 20 minutes south of Kingman, wild burros in the street, a genuine ghost-town feel. Worth it if you’re ahead of schedule; skip it if LA traffic is already building. Then I-40 to Barstow, I-15 to I-10, and west — ~320 miles of desert and sprawl. Audiobook territory: this is what the long miles are for.

Evening: the Pier

The Santa Monica Pier — free, open daily — and the “End of the Trail” sign at the pier’s west end. Take the photo (the bookend to Day 1’s Begin sign), then walk the pier: the Pacific Wheel — the world’s first solar-powered Ferris wheel — the arcade, the street performers. Rides run ~$10–12 each; the sunset over the Pacific is free. Dinner on the pier (the Lobster for the view) or on Main Street in Ocean Park. You drove 2,448 miles to watch the sun drop into the ocean — let it take its time.

Where to stay

Santa Monica — near the Pier for the last night. Shore Hotel (steps from the Pier, $270–$400) or a Main Street spot in Ocean Park for half that. Return the rental car tomorrow — tonight is for the ocean.

Bad-weather plan

The Pier is an any-weather finale — the arcade and the carousel are covered, and a marine-layer sunset is still a sunset. The Getty Villa (free, timed tickets) is the classy rain backup.

Flagstaff to Santa Monica: ~465 mi, 7 hr · Seligman: Snow Cap Drive-In, from 1953 · Pier: free, open daily · End of the Trail sign at the pier’s west end