Why this drive
America's most iconic road trip, and a wonderful one at an unhurried pace
Route 66 is the original American road trip: 2,278 miles of two-lane history running from downtown Chicago to the Santa Monica Pier, through eight states and three time zones. Along the way you pass hand-painted signs and restored neon, diners that have been frying eggs since the 1920s, teepee-shaped motels, the Cadillac Ranch, and long, cinematic stretches of open Western sky. In 2026 the Mother Road turns 100, and there has never been a better year to drive it.
What makes Route 66 such a good fit for travelers over 50 is that the joy is in the stopping, not the striding. The neon, the murals, the classic diners, and the roadside giants are all seen from the car, the sidewalk, or a short flat stroll, not a strenuous hike. Driven the way we lay it out here, heading west from Chicago over about 14 days, the daily legs stay short, each base town is comfortable and walkable, and you never have to rush. This guide covers the full route and driving distances, a relaxed day-by-day itinerary, the best base towns and senior-friendly hotels, and honest advice on desert heat, one-way car rentals, and accessibility.
The Road Trip Route
The Route 66 route map and driving distances
This Route 66 road trip map traces a one-way drive of about 2,278 miles from Chicago to Santa Monica along historic Route 66, heading west through all eight states, Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California, driven the classic direction so the landscape opens up ahead of you the whole way.
🛣️ Chicago to Santa Monica · about 2,278 miles
CHICAGO → ST. LOUIS → OKLAHOMA CITY → AMARILLO → SANTA FE → FLAGSTAFF → SANTA MONICA
- 1
🏙️ Chicago, IL
Fly into O'Hare or Midway · the “Begin Route 66” sign
- 🚗 ~300 mi · 5h
- 2
🌉 St. Louis, MO
The Gateway Arch and frozen custard
- 🚗 ~500 mi · 8h (via Tulsa)
- 3
🤠 Oklahoma City, OK
Cowboy country and Bricktown
- 🚗 ~260 mi · 4h
- 4
🎨 Amarillo, TX
Cadillac Ranch and the Texas panhandle
- 🚗 ~290 mi · 4h30
- 5
🏝️ Santa Fe & Albuquerque, NM
Adobe plazas and the high desert
- 🚗 ~380 mi · 6h
- 6
🌲 Flagstaff, AZ
Cool pines and the Grand Canyon gateway
- 🚗 ~470 mi · 7h30
- 7
🏖️ Santa Monica, CA
The Pier, the “End of the Trail” sign · fly out of LAX
The itinerary
A senior-paced day-by-day Route 66 itinerary
Fourteen unhurried days from Chicago to Santa Monica, with short daily drives, comfortable overnight bases, and time to actually stop for the neon, the diners, and the views. Trim to ten for the highlights, or stretch to three weeks to savor every mile.
Days 1-2
Arrive & Chicago
Fly into O'Hare or Midway and settle into Chicago for two nights. Photograph the “Begin Route 66” sign on Adams Street across from the Art Institute, ride the flat Loop, and have a deep-dish dinner before you point the car west. Pick up your one-way rental here.
Day 3
Chicago to St. Louis
An easy first leg (about 300 miles) down old Illinois 66 past Pontiac's murals, the Gemini Giant, and the neon of Springfield. Arrive in St. Louis for the night beneath the Gateway Arch.
Day 4
St. Louis to Springfield, Missouri
A gentle Missouri day (about 215 miles) through the Ozark hills, with an easy stop at Meramec Caverns and the painted barns and murals of Cuba. Overnight in Springfield, the birthplace of Route 66.
Day 5
Springfield to Oklahoma City
Cross the famous 13-mile sliver of Kansas (Galena's vintage garage) and roll through Tulsa's Art Deco downtown and the Blue Whale of Catoosa on the way to Oklahoma City (about 250 miles).
Day 6
Oklahoma City
A rest day in cowboy country: the National Cowboy & Western Heritage Museum, the walkable Bricktown canal, and the moving Oklahoma City National Memorial, all flat and easy.
Day 7
Oklahoma City to Amarillo
Into the Texas panhandle (about 260 miles) past the leaning water tower at Groom and the Cadillac Ranch, where you can spray-paint a fin. A steak at the Big Texan caps the night.
Day 8
Amarillo to Santa Fe
West into New Mexico (about 290 miles), pausing at Tucumcari to see the restored neon of the Blue Swallow Motel, then climbing the old Santa Fe loop to the adobe capital for the night.
Day 9
Santa Fe & Albuquerque
Wander Santa Fe's flat central plaza and galleries in the morning, then drop down to Albuquerque's Old Town and the Sandia Peak Tramway. Two nights in the high desert lets you slow right down.
Day 10
Albuquerque to Flagstaff
A big-sky day (about 325 miles) past Gallup's historic El Rancho Hotel, the Petrified Forest, and Winslow, where you really can stand on the corner. Meteor Crater is a short detour before Flagstaff's cool pines.
Day 11
Grand Canyon day trip
From Flagstaff it is about 80 minutes to the South Rim. Spend the day on the flat, paved Rim Trail and the shuttle-served overlooks, then return to Flagstaff (or nearby Williams) for the night.
Days 12-13
Flagstaff to Santa Monica
The final push (about 470 miles over two easy days) through Seligman's kitschy heart of Route 66, the gold-rush hills toward Oatman, and the Mojave, with an overnight around Barstow before the run to the coast.
Day 14
Santa Monica & the finish
Reach the Santa Monica Pier and the “End of the Trail” sign, where the Mother Road meets the Pacific. Celebrate, then fly home from LAX, or linger a few days in Los Angeles.
Arrival & departure
Where to fly in and out
This is a one-way drive, so fly into one airport and out of another to avoid a 2,000-mile backtrack. Chicago is the natural start: O'Hare (ORD) is one of the world's largest hubs, and Midway (MDW) is smaller and often cheaper. Los Angeles (LAX) is the finish, a short hop from the Santa Monica Pier, though smaller Hollywood Burbank (BUR) can be gentler. Pick your rental car up at the arrival airport and drop it at the departure one, and budget for a one-way drop-off fee. For your last night you can linger on the coast in Santa Monica or bed down near LAX for an easy morning flight; we list senior-friendly hotels at every base town below.
✈️ Compare flights to Chicago and from Los Angeles
An open-jaw ticket (into Chicago, out of LAX) usually costs about the same as a round trip and saves you the long drive home. Midweek departures bring the best fares.
Getting around
Renting a car and driving Route 66
A rental car is essential; the whole point is the drive. Pick the car up in Chicago and drop it at LAX, budgeting for a one-way, cross-country drop-off fee. Keep the daily legs short, most are three to five hours, with frequent stops for the neon, the diners, and the roadside giants.
A few Route 66 realities are worth planning around. The road was decommissioned in 1985, so it is not a single route on your GPS; follow the brown “Historic Route 66” signs, and consider the EZ66 Guide or the Route 66 Navigation app to stay on the old alignments. Interstate 40 parallels much of the western route, so you can always hop on it to skip a dull stretch or beat weather. Through the New Mexico, Arizona, and California deserts the heat is serious from late spring through early fall, so carry water, keep the tank above half, and drive in the cooler mornings. And remember you cross three time zones heading west, gaining an hour each time.
🚗 Renting a car
Best for almost everyone on a one-way cross-country drive
Pros
- A fresh, reliable vehicle with modern safety features and strong air-conditioning for 2,278 desert miles
- No wear, mileage, or breakdown risk on your own car far from home
- Fly in and start fresh, and choose the right size: a higher SUV for easy entry, or an economy car to save
- Roadside assistance and a replacement vehicle if anything goes wrong on a remote stretch
Cons
- Daily rental and insurance costs add up over a two-week trip
- A one-way drop-off fee for picking up in Chicago and returning at LAX can be steep coast to coast
- A day or two to get comfortable with an unfamiliar vehicle
🏠 Driving your own car
Best only if you live near Chicago and have plenty of time
Pros
- No rental or rental-insurance cost, often the single biggest saving on the trip
- A familiar, comfortable vehicle you already know and trust
- Pack freely with no baggage limits, and bring your own cooler, layers, and gear
- No airport lines, one-way charges, or drop-off fees
Cons
- You finish 2,278 miles from where you started, so you must drive the length back or ship the car home
- Real wear, mileage, and time added to your own vehicle
- No easy vehicle swap if you break down on a remote desert stretch
🚗 Rental cars for Route 66
Book early and confirm the one-way drop-off fee up front. A comfortable mid-size or SUV with strong air-conditioning and good visibility suits the long desert miles best.
Base town 1 of 7 · Chicago
Chicago, Illinois
Route 66 begins in the heart of downtown Chicago, and it is worth giving the city two full days before you drive west. The official “Begin Route 66” sign stands on Adams Street, right across from the Art Institute, and almost everything a visitor wants is within the flat, walkable Loop.
Chicago is one of America's great cities for the culture-minded traveler over 50: world-class museums, the lakefront, architecture cruises, and deep-dish pizza, all easy to reach. Pick up your one-way rental car here once you are ready to point the car west.
Top things to do (senior-friendly)
- Photograph the “Begin Route 66” sign on Adams Street and tour the Art Institute across the road
- Stroll Millennium Park and “The Bean,” all flat and paved
- Take an architecture river cruise, the city's best sightseeing, from a comfortable seat
- Ride to the Skydeck at Willis Tower for the classic skyline view
- Have a deep-dish dinner in the Loop before you drive west
Time needed: 1 to 2 full days (2 nights)Dining: Deep-dish pizza, Italian beef, and Loop steakhouses
Senior tip: Base yourself in the Loop or on South Michigan Avenue so the Begin sign, the Art Institute, and Millennium Park are all a flat walk away, and pick up your rental car on your last morning to skip downtown parking fees.
🏨 Where to stay in Chicago: three senior-friendly picks
SplurgePalmer House, a Hilton Hotel
A grand, historic Loop landmark with a jaw-dropping lobby, steps from the “Begin Route 66” sign and the Art Institute. Central, storied, and elegant.
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ComfortableHilton Chicago
A classic full-service hotel facing Grant Park on South Michigan Avenue, an easy walk to Millennium Park and the museums, with a pool and plenty of space.
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ValueHampton Inn Chicago Downtown/N Loop
A dependable, well-located pick with free hot breakfast, walkable to the river, the Loop, and the Magnificent Mile.
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Base town 2 of 7 · St. Louis
St. Louis, Missouri
About 300 miles down old Illinois 66, St. Louis marks the Mississippi River and the end of the Midwest leg. The Gateway Arch rises right on the riverfront, and the tram to the top is a gentle, seated ride to one of the country's great views.
The city makes an easy overnight, with a walkable riverfront, several free major attractions, and the famous frozen custard at Ted Drewes on the old road out of town. One night is plenty before you head into the Ozarks.
Top things to do (senior-friendly)
- Ride the tram to the top of the Gateway Arch, a seated, drive-up icon
- Explore the free, ground-level Museum at the Gateway Arch
- Visit Forest Park's free zoo and art museum, flat and easy
- Tour the Anheuser-Busch brewery and see the Clydesdales
- Stop for frozen custard at Ted Drewes on Chippewa Street, pure Route 66
Time needed: 1 full day (1 night)Dining: Toasted ravioli, barbecue, and Ted Drewes frozen custard
Senior tip: Stay near the Arch or downtown so the riverfront and the tram are a short, flat walk, and time your Arch tram ride for late afternoon when the light over the river is best.
🏨 Where to stay in St. Louis: three senior-friendly picks
SplurgeUnion Station Hotel, Curio Collection by Hilton
A spectacular restored 1894 train station with a soaring Grand Hall, a nightly light show, and an aquarium on site. Historic and memorable.
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ComfortableHyatt Regency St. Louis at The Arch
A full-service hotel directly across from the Gateway Arch, with river and Arch views and the riverfront at your door.
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ValueDrury Plaza Hotel St. Louis at the Arch
A dependable downtown pick in a handsome historic building, with free hot breakfast and evening snacks and drinks, steps from the Arch.
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Base town 3 of 7 · Oklahoma City
Oklahoma City, Oklahoma
Between St. Louis and Oklahoma City you cross the tiny 13-mile sliver of Kansas and roll through Tulsa's handsome Art Deco downtown. Oklahoma City itself makes a comfortable two-night base in the heart of cowboy country, with wide, easy streets and a revitalized center.
The city's star attraction, the National Cowboy & Western Heritage Museum, is a beautifully accessible indoor experience, and the Bricktown canal district is flat and walkable. The Oklahoma City National Memorial is a moving, gentle stop.
Top things to do (senior-friendly)
- Explore the National Cowboy & Western Heritage Museum, all indoors and accessible
- Walk or take a water-taxi along the flat Bricktown canal
- Pay respects at the Oklahoma City National Memorial & Museum
- See the Blue Whale of Catoosa and Tulsa's Art Deco on the way in
- Browse Stockyards City for boots, hats, and a classic steakhouse lunch
Time needed: 1 to 2 full days (2 nights)Dining: Chicken-fried steak, barbecue, and Stockyards steakhouses
Senior tip: Downtown and Bricktown hotels put the canal, the memorial, and good dining within a flat walk. Break the long St. Louis-to-Oklahoma City leg with a lunch stop in Tulsa rather than pushing straight through.
🏨 Where to stay in Oklahoma City: three senior-friendly picks
SplurgeThe Skirvin Hilton Oklahoma City
A restored 1911 landmark in the heart of downtown, full of character, with a pool and easy access to Bricktown and the memorial.
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ComfortableHampton Inn & Suites OKC-Bricktown
A reliable, modern hotel right in Bricktown, with free hot breakfast and the canal and restaurants at your doorstep.
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ValueHoliday Inn Express OKC Downtown-Bricktown
A dependable, central value pick with free breakfast and an indoor pool, walkable to Bricktown and the memorial.
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Base town 4 of 7 · Amarillo
Amarillo, Texas
Into the Texas panhandle, Amarillo is Route 66 at its most gloriously kitschy. Just west of town, the Cadillac Ranch tilts ten graffiti-covered Cadillacs nose-down in a field, and you are handed a can of spray paint to leave your mark, a short, flat walk from the pull-off.
In town, the Big Texan Steak Ranch serves its famous 72-ounce steak challenge beneath towering neon, and the restored San Jacinto district preserves classic Route 66 storefronts. It makes an easy, fun overnight.
Top things to do (senior-friendly)
- Spray-paint a fin at the Cadillac Ranch, a short flat walk from the road
- Dine under the neon at the Big Texan Steak Ranch
- Browse the vintage 66 storefronts of the San Jacinto district
- See the leaning water tower at Groom on the way in
- Detour to the rim overlooks of Palo Duro Canyon, the “Grand Canyon of Texas”
Time needed: 1 full day (1 night)Dining: Texas steaks, barbecue, and the Big Texan
Senior tip: Wear closed shoes at the Cadillac Ranch, as the field is often muddy. The Big Texan runs a free shuttle to and from many Amarillo hotels, a nice touch if you would rather not drive to dinner.
🏨 Where to stay in Amarillo: three senior-friendly picks
SplurgeThe Barfield, Autograph Collection
A stylish restoration of a 1920s downtown high-rise, the most polished stay in Amarillo, with a rooftop bar and easy access to the historic district.
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ComfortableCourtyard by Marriott Amarillo Downtown
A comfortable, modern hotel in a converted historic building downtown, walkable to restaurants and the 66 storefronts.
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ValueThe Big Texan Motel
A Route 66 icon beside the Big Texan Steak Ranch, with a Texas-shaped pool, neon, and cowboy kitsch. Fun, affordable, and pure Mother Road.
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Base town 5 of 7 · Santa Fe & Albuquerque
Santa Fe & Albuquerque, New Mexico
New Mexico is many travelers' favorite stretch of Route 66. The early alignment loops up to Santa Fe, the country's oldest and highest state capital, a walkable adobe city of galleries, museums, and a historic central plaza, all flat and compact.
An hour south, Albuquerque carries the main Route 66 line straight through town along Central Avenue, with its restored neon, the charming Old Town plaza, and the Sandia Peak Tramway. Two nights here, whether you split them or base in one city, let you slow to the high-desert pace.
Top things to do (senior-friendly)
- Wander Santa Fe's flat central plaza, galleries, and the Palace of the Governors
- Ride the Sandia Peak Tramway above Albuquerque for a seated mountain view
- Explore Albuquerque's Old Town plaza and its adobe shops and churches
- See the restored Route 66 neon along Central Avenue after dark
- Visit the Indian Pueblo Cultural Center for living Native culture
Time needed: 2 full days (2 nights)Dining: New Mexican chile, blue-corn enchiladas, and sopaipillas
Senior tip: Santa Fe sits at 7,000 feet, so take altitude gently your first day, drink plenty of water, and pace the gentle hills around the plaza. If steps and cobbles are a concern, base in Albuquerque's flatter Old Town and day-trip up to Santa Fe.
🏜️
Full destination guide
The complete senior's guide to Santa Fe
The plaza, the galleries and museums, the best adobe hotels, and the easiest ways to enjoy the city over 50.
Read the Santa Fe guide →
🏨 Where to stay in Santa Fe & Albuquerque: three senior-friendly picks
SplurgeLa Fonda on the Plaza
The historic inn at the end of the Santa Fe Trail, right on the plaza, full of hand-painted Southwestern character, with a rooftop bar and everything walkable.
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ComfortableHotel Chimayo de Santa Fe
A warm, colorful hotel a block off the plaza, central and comfortable, with an elevator and easy, flat access to the galleries and restaurants.
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ValueHotel Albuquerque at Old Town
A handsome Southwestern hotel right at Albuquerque's Old Town plaza, with a pool, gardens, and good value on the flatter, warmer end of the route.
Check rates →
Base town 6 of 7 · Flagstaff
Flagstaff, Arizona
After the long high-desert crossing, past Gallup, the Petrified Forest, and Winslow's famous corner, Flagstaff is a welcome change: a cool, pine-scented mountain town at 7,000 feet with a walkable, historic Route 66 downtown of brick storefronts and old hotels.
Flagstaff is also the gateway to the Grand Canyon's South Rim, about 80 minutes north, which makes a superb day trip. Red-rock Sedona and the Route 66 town of Williams are both close too. Two nights here gives you a canyon day and a downtown day.
Top things to do (senior-friendly)
- Day-trip to the Grand Canyon's flat, paved South Rim overlooks
- Stroll Flagstaff's historic Route 66 downtown and its brewpubs
- Visit Lowell Observatory, where Pluto was discovered, for an easy evening
- Ride the vintage train from Williams to the canyon rim
- Detour to the red-rock overlooks of nearby Sedona
Time needed: 1 to 2 full days (2 nights)Dining: Southwestern fare, brewpubs, and hearty mountain comfort food
Senior tip: Flagstaff's altitude and the Grand Canyon rim both sit near 7,000 feet and can leave you short of breath, so take the first day easy and carry water. In summer, do the canyon in the morning before the afternoon heat and storms.
🏔️
Full destination guide
The complete senior's guide to the Grand Canyon
The accessible South Rim overlooks, the free shuttle, the easiest trails, and where to stay, all at a gentle pace.
Read the Grand Canyon guide →
🏔️
Full destination guide
The complete senior's guide to Sedona
The red-rock views you can reach by car, the gentle trails and scenic drives, and where to stay.
Read the Sedona guide →
🏨 Where to stay in Flagstaff: three senior-friendly picks
SplurgeLittle America Hotel Flagstaff
A spacious, forest-set hotel with big rooms, a pool, and pine-shaded grounds, a relaxing, easy-access base a short drive from downtown.
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ComfortableDrury Inn & Suites Flagstaff
Dependable and central, with free hot breakfast and evening snacks and drinks and an indoor pool, well placed for the canyon day trip.
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ValueGrand Canyon Railway Hotel (Williams)
In the Route 66 town of Williams, this comfortable hotel pairs with the vintage train to the canyon rim, a fun, good-value alternative gateway.
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Base town 7 of 7 · Santa Monica
Santa Monica, California
The final run drops out of the mountains through Seligman, Kingman, and the Mojave, then into greater Los Angeles and down to the sea. Route 66 ends at the Santa Monica Pier, where the “End of the Trail” sign marks 2,278 miles completed and the Pacific stretches out beyond the boardwalk.
Santa Monica is a relaxed, walkable beach town and a wonderful place to celebrate the finish, with a flat oceanfront promenade, the pedestrian Third Street shops, and easy sunsets over the water. Stay a night or two before you fly home from nearby LAX.
Top things to do (senior-friendly)
- Reach the “End of the Trail” sign at the Santa Monica Pier
- Stroll the flat oceanfront path and the Third Street Promenade
- Ride the pier's vintage carousel and Ferris wheel
- Watch the sunset over the Pacific from bluff-top Palisades Park
- Take a gentle, level beach-path surrey or bike ride
Time needed: 1 to 2 nightsDining: Fresh seafood, California cuisine, and pier snacks
Senior tip: Pier and beachfront parking is scarce and pricey, so a hotel near the promenade lets you leave the car and walk. If your flight out of LAX is early, a hotel near the airport makes the last morning far easier.
🏨 Where to stay in Santa Monica: three senior-friendly picks
SplurgeShutters on the Beach
An elegant Cape Cod-style hotel right on the sand, steps from the pier, the finest, most celebratory finish to the Mother Road.
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ComfortableLe Meridien Delfina Santa Monica
A polished, comfortable hotel a few flat blocks from the beach and the promenade, with a pool and easy walking to everything.
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ValueHampton Inn & Suites Santa Monica
A dependable, well-placed pick with free hot breakfast, walkable to the promenade and a short ride to the pier and the beach.
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Worth the detour
Side trips to add if you have extra days
Route 66 is lined with worthwhile detours. If you can stretch the trip, these sit close to the route and are all gentle for travelers over 50.
The Grand Canyon, in depth
Rather than a day trip from Flagstaff, spend a night at the South Rim so you can watch both sunset and sunrise over the canyon from the flat, paved rim path. It is the greatest natural wonder anywhere near the route.
Palo Duro Canyon (Amarillo)
Just south of Amarillo, the second-largest canyon in the country has scenic drive-up overlooks and an easy rim, a striking and uncrowded stop.
Sedona's red rocks
An hour from Flagstaff, Sedona's cathedral formations are reached by paved scenic drives and short, level paths, a gorgeous half-day.
Meramec Caverns (Missouri)
One of Route 66's original roadside attractions, with lit, paved cavern walkways and a classic barn-advertised history.
Oatman (Arizona)
Over the winding Sitgreaves Pass, this old mining town has wild burros wandering Main Street. The drive is slow and curvy, so take it in daylight and at your own pace.
Continue on the Pacific Coast Highway
Because Route 66 ends near Los Angeles, it connects neatly to another classic. With extra time, keep driving up the Pacific Coast Highway for the ultimate California finale.
When to go
The best time to drive Route 66
Season matters on Route 66, because the same western deserts that are glorious in spring turn dangerously hot in summer, while the high towns can see snow in winter. For travelers over 50, the shoulder seasons are not just nicer, they are safer and far more comfortable.
April - early JuneOur top pick. Mild days across the plains and the desert, wildflowers, and manageable crowds before the summer heat arrives.
Mid-June - AugustThe classic but hottest season: the New Mexico, Arizona, and California deserts regularly top 100°F. Drive early, rest mid-day, and hydrate constantly.
September - OctoberThe other sweet spot, and many travelers' favorite. Comfortable temperatures, golden light, thinner crowds, and the heart of the 2026 centennial events.
November - MarchQuiet and atmospheric, but Santa Fe and Flagstaff (near 7,000 feet) can see snow and icy passes. The southwestern deserts stay pleasant. For confident cold-weather drivers.
Come prepared
What to pack for a Route 66 road trip
Route 66 crosses three climates in two weeks, from cool Midwest mornings to blazing desert afternoons, so pack for range. The essentials that matter most for older travelers:
- Layers for everything: cool mornings, hot afternoons, and chilly high-altitude evenings in Santa Fe and Flagstaff
- Sturdy, closed-toe walking shoes with good grip, plus comfortable sandals for the car
- A wide-brim hat, high-SPF sunscreen, and polarized sunglasses for the relentless desert sun
- A refillable water bottle per person and a cooler in the car; services can be an hour apart out west
- Any regular medications in your carry-on, plus a small first-aid kit
- The EZ66 Guide or the Route 66 Navigation app, and a paper atlas, since GPS will not route the historic road
- Some cash for small-town diners, tips, and older motels
🛒 Road trip gear we recommend
A little preparation makes every day on the road easier, and a few smart buys before you leave save real hassle once you are out on the Mother Road. These are the senior-tested items we would not drive Route 66 without. Click any pick to compare current options and read the reviews before you pack.
Collapsible cooler
Keep water and snacks cold on the long stretches between towns.
View dealsWide-brim sun hat
Real shade for the exposed, high-UV desert miles.
View dealsInsulated water bottles
Dehydration is a real risk across the western deserts.
View dealsPhone dash mount
Keep the navigation app in view as you follow the old alignments.
View dealsMemory-foam seat cushion
Comfort that pays off on the longer driving days.
View dealsRoute 66 guidebook
The EZ66 Guide keeps you on the historic road where GPS won't.
View deals
Know before you go
Senior travel tips for Route 66
🧭 The single most useful thing for Route 66: Because the road was decommissioned in 1985, it will not appear as one route on your GPS. Pick up the EZ66 Guide by Jerry McClanahan or load the Route 66 Navigation app before you go, and follow the brown Historic Route 66 signs. It is the difference between cruising the historic alignments and accidentally spending the day on Interstate 40.
🏝️
Beat the desert heat
From June through September the New Mexico, Arizona, and California deserts regularly top 100°F. Drive in the cool of the morning, rest through the afternoon, and always carry water in the car.
⛰️
Mind the altitude
Santa Fe and Flagstaff both sit near 7,000 feet. Arrive slowly, hydrate, and watch for headaches or breathlessness your first day at elevation.
🛏️
Book the landmark motels early
The historic motels like the Blue Swallow and El Rancho have only a handful of rooms and fill months ahead, more so in the 2026 centennial year.
⛽️
Gas up often
Services are sparse across the western stretches, so keep the tank above half and top up whenever you pass a station.
♿
Choose your comfort level
Vintage motels are full of character but can mean stairs and small bathrooms; ask for ground-floor or accessible rooms, or mix in modern chain hotels for an easy night.
🐢
Pace yourself
Keep the daily legs to three to five hours, build in a rest day, and remember the stops, not the miles, are the whole point of Route 66.
🛡️ Protect your trip
With hotels booked months ahead and long drives through remote desert country, travel insurance earns its place on Route 66, covering trip cancellation, medical care, and emergency help far from the nearest hospital.
Get a travel insurance quote →
Explore at your own pace
Self-guided audio tours for the drive
Route 66 is all about the drive, which makes a GPS-narrated audio tour a natural fit, and a particularly good one for travelers over 50. As you drive, a guide plays on your phone and tells the story of what you are passing, the ghost towns, the neon, the diners, and the history of the Mother Road, with no schedule to keep and no group to follow. You stop as long as you like wherever you please and go entirely at your own pace. Apps such as Route 66 Navigation are built for the route; download any audio tour before you set out, as cell service is patchy across the desert.
🛣️ The self-guided Route 66 drive
Common questions
Route 66 Road Trip FAQ
The questions senior travelers ask most about driving Route 66 from Chicago to Santa Monica.
What is Route 66? +
Route 66 is the most famous highway in the United States, a 2,278-mile road running from Chicago, Illinois, to Santa Monica, California. Nicknamed the Mother Road, it was established in 1926 and became the great vacation and migration route across the American heartland. Though it was decommissioned as a federal highway in 1985, most of historic Route 66 is still drivable today and is lined with vintage neon, classic diners, and roadside Americana. In 2026 it celebrates its 100th anniversary.
Where does Route 66 start and end? +
Route 66 officially begins in downtown Chicago at the corner of Adams Street and Michigan Avenue, marked by the Begin Route 66 sign across from the Art Institute. It ends 2,278 miles later at the Santa Monica Pier in California, where the End of the Trail sign overlooks the Pacific. Most travelers drive it east to west, from Chicago to Santa Monica, the classic direction.
How long is Route 66, and how long does it take to drive it? +
Historic Route 66 is about 2,278 miles long. You could cover it in five or six days of hard interstate driving, but that misses the point. For a relaxed, senior-paced trip that leaves time to stop for the neon, the diners, and the sights, plan on about 14 days, a comfortable 150 to 250 miles a day. Ten days covers the highlights; three weeks lets you truly linger.
What states does Route 66 go through? +
Route 66 passes through eight states on its way from Chicago to Santa Monica: Illinois, Missouri, a short 13-mile stretch of Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. Along the way it crosses three time zones, so you gain an hour each time you move west into a new one.
Can you still drive the original, historic Route 66? +
Yes, mostly. Route 66 was decommissioned as a federal highway in 1985, so it will not show up as a single route on your GPS, but roughly 85 percent of the historic road is still drivable. Follow the brown Historic Route 66 signs, and use the EZ66 Guide or the Route 66 Navigation app to stay on the old alignments. Interstate 40 parallels much of the western route if you ever want to skip a stretch.
Is Route 66 safe to drive? +
Route 66 is a safe and rewarding drive for careful travelers over 50, though a few stretches call for planning. The long, empty desert sections in New Mexico, Arizona, and California can be hot and remote, so carry water, keep the fuel tank above half, and drive them in the cooler morning hours. A few original alignments are gravel or winding, such as the Sitgreaves Pass near Oatman, so take those slowly and only in daylight, or stay on the paved main route. Keep the daily legs short and you will find it a gentle, unhurried drive.
When is the best time to drive Route 66? +
Late spring, May into June, and early fall, September into October, are ideal, with mild days across the plains and the desert. Summer is the busiest season but brings serious desert heat in New Mexico, Arizona, and California. Winter can bring snow and icy passes at the high-altitude towns like Santa Fe and Flagstaff, though the southwestern deserts stay pleasant.
What are the must-see stops and attractions on Route 66? +
The classic Route 66 stops include the Begin Route 66 sign in Chicago, the Gateway Arch in St. Louis, the Blue Whale of Catoosa near Tulsa, the Cadillac Ranch in Amarillo, the restored Blue Swallow Motel neon in Tucumcari, the adobe plazas of Santa Fe and Albuquerque, the corner in Winslow, Arizona, the kitschy town of Seligman, the Wigwam Motel, a Grand Canyon day trip from Flagstaff, and the End of the Trail sign at the Santa Monica Pier.
Where should I fly in and out for a Route 66 road trip? +
Because Route 66 is a one-way drive, fly into Chicago, using either O'Hare (ORD) or the smaller, often cheaper Midway (MDW), and out of Los Angeles (LAX), which is close to the Santa Monica finish. Book an open-jaw ticket, pick up your rental car at the arrival airport, and drop it at the departure one, budgeting for a one-way drop-off fee.
Can you do Route 66 by train? +
Not the whole way, but partly. No single train follows Route 66 end to end, yet Amtrak's Southwest Chief runs daily between Chicago and Los Angeles and parallels much of the western route, stopping in Route 66 towns such as Flagstaff, Kingman, and Albuquerque. The vintage Grand Canyon Railway also runs from Williams to the canyon rim. To actually see the roadside Route 66, though, driving is the way to do it.
Is Route 66 a good road trip for seniors? +
Yes, it is one of the best. Almost all of the great sights, the murals, the neon, the roadside giants, and the classic diners, are enjoyed from the car, the sidewalk, or a short flat stroll rather than a strenuous hike. With short daily drives, walkable overnight towns, and a strong dose of nostalgia, it suits travelers over 50 beautifully.
Is 2026 a special year to drive Route 66, and what festivals are there? +
Very much so. Route 66 turns 100 on November 11, 2026, and the centennial fills the year with festivals, car shows, and special events all along the route, including the popular Route 66 festival in Springfield, Missouri, and neon and balloon events out west. It is a wonderful time to make the drive, but demand for the historic motels runs high, so book your overnights earlier than usual.