As the sun sets over the vast Painted Desert, casting a golden glow on the ancient petrified logs that dot the landscape, it’s hard not to feel the pull of history. In 2026, Route 66 turns 100 years old – a milestone that invites road warriors, history buffs, and dreamers from around the world to hit the pavement and trace the path of America’s most iconic highway. Established on November 11, 1926, this 2,448-mile ribbon of asphalt from Chicago, Illinois, to Santa Monica, California, has symbolized freedom, resilience, and the great American road trip for a century. And right in the heart of it all? Holbrook, Arizona – a quirky, welcoming stop where the spirit of the Mother Road comes alive in neon-lit motels and dinosaur-themed rock shops.
Whether you’re planning a full coast-to-coast odyssey or a segment focused on the Southwest’s red-rock wonders, 2026 promises extra magic with special events, restored landmarks, and centennial commemorations. From roaring twenties-themed kickoffs to multi-day festivals, the year will buzz with energy. As Holbrook’s proud stewards, we’re thrilled to spotlight our town as a must-visit gem on this historic route. Grab your maps, pack your snacks, and let’s dive into the ultimate guide to celebrating Route 66’s 100th birthday – with plenty of detours through our sunny corner of Arizona.
A Quick History Lesson
The Birth of an Icon
Route 66 wasn’t just a highway; it was a lifeline. Born in the Roaring Twenties as part of the U.S. Highway System, it connected bustling cities to dusty frontiers, offering jobs during the Great Depression and escape routes for Dust Bowl migrants immortalized in John Steinbeck’s The Grapes of Wrath.
Post-War Boom and Modern Revival
Post-World War II, it became the artery for families chasing the California dream in shiny new Chevys, fueled by diners, drive-ins, and roadside oddities. By the 1980s, interstates like I-40 overshadowed it, but Route 66 refused to fade. Designated a National Scenic Byway in 1985 and an All-American Road in 2001, it’s now a UNESCO World Heritage contender, preserved through the passion of communities like ours in Holbrook. The centennial in 2026 marks not just 100 years of pavement but a century of stories – from Navajo traders to Hollywood stars. Expect nationwide tributes, including a special U.S. Mint coin and new interpretive monuments along the way.
Planning Your Centennial Road Trip
When and How to Go
Timing is everything on Route 66, especially in the anniversary year. Aim for spring (April-June) or fall (September-October) to dodge summer heat and winter snow. In 2026, overlap your trip with major events for that extra spark – like the Historic Route 66 Association of Arizona’s Fun Run from May 1-3, a convoy of classic cars cruising the state’s stretch. Or join the Texas Route 66 Festival from June 4-13, featuring car shows and bus tours. Missouri kicks things off with a grand event on April 30 in Springfield.
Logistics and Budget
How long? A leisurely two-week drive covers the full route at 150-200 miles per day, leaving time for detours. Go east-to-west for the classic narrative arc, or west-to-east if you’re starting from Arizona. Rent a convertible for flair, or an RV for comfort – just watch those low bridges! Budget $2,000-$4,000 per person for gas, lodging, and meals, plus event tickets.
Packing and Safety
Download apps like Roadtrippers or the EZ66 Guide for real-time navigation, and join the Route 66 Centennial Commission for official updates. Pack light: Comfortable shoes for hiking, a cooler for picnic suppers, and a journal for scribbling tales of eccentric motel owners. Safety first – cell service spotty, so download offline maps, carry water (especially in the desert), and respect speed limits on curvy alignments. And don’t forget your camera; 2026 will be photogenic overload.
Your Mile-by-Mile Itinerary
Here’s a state-by-state blueprint, blending must-sees with hidden gems, presented in the correct sequential order for an east-to-west journey. We’ve flagged Holbrook as your Arizona anchor – because no Route 66 trip is complete without our petrified wonders and teepee sleeps.
Illinois: The Windy City Launchpad (Days 1-2, ~300 miles)
Chicago to Joliet
Kick off at the official “End of the Trail” sign in Chicago’s Grant Park, where Lake Michigan meets the urban hustle. Snap a selfie with the Willis Tower in the background, then cruise southwest through Joliet’s Rialto Square Theatre – a 1920s movie palace that’s hosted everyone from Al Joliet to modern films.
Pontiac to Springfield
In Pontiac, the Route 66 Hall of Fame Museum dishes murals and memorabilia. Push to Springfield for Abraham Lincoln’s home and tomb, plus the Cozy Dog Drive-In, birthplace of the corn dog. Overnight at the Dell Rhea’s Chicken Basket for fried fowl and history. Centennial tip: Look for Chicago’s jazz-fueled launch parties in early 2026.
Missouri: Archways and Caverns (Days 3-4, ~320 miles)
St. Louis Highlights
Cross the Chain of Rocks Bridge into Missouri – a rickety 1927 span with a mid-river water intake that’s pure photo bait. St. Louis greets with the gleaming Gateway Arch; ride to the top for panoramic views, then explore the National Museum of Transportation’s vintage autos.
Springfield and Beyond
Detour to Meramec Caverns for glowing stalactites and outlaw lore (Jesse James hid here). In Springfield, the Route 66 Car Museum revs up with hot rods, and don’t miss the Fantastic Caverns – a tram ride through underground wonders. Missouri’s April 30 centennial bash in Springfield will feature live music and fireworks. Stay at the Munger Moss Motel for that classic neon vibe.
Oklahoma: Whales, Barns, and Pops (Days 5-6, ~400 miles)
Miami to Tulsa
The Sooner State claims the most miles of original 66 – over 400! Start in Miami with the Coleman Theatre’s vaudeville ghosts, then Catoosa’s Blue Whale: a 1970s swimming spot turned folk art icon. Claremore’s J.M. Davis Arms & Historical Museum packs 12,000 guns (yes, really).
Arcadia to Oklahoma City
Arcadia’s Round Barn is a 1898 architectural marvel. Tulsa offers art deco skyscrapers and the Philbrook Museum of Art, while Oklahoma City’s Milk Bottle Grocery is a tiny 1930s relic. End at the Pops soda bottle sculpture – lit up with 176 flavors inside. Oklahoma’s 2026 calendar brims with centennial rides; check their association for pop-up parades.
Texas: Big Skies and Cadillacs (Days 7-8, ~200 miles)
Shamrock to Amarillo
Texas keeps it short but punchy. Shamrock’s U-Drop Inn, inspiration for Pixar’s Cars Tower of Terror, is a streamlined diner dream. Amarillo’s Golden Driller statue towers 67 feet, but the real star? Cadillac Ranch – ten Caddies buried nose-down in a field, perfect for spray-paint tagging (bring your own cans).
Midpoint and Beyond
The Midpoint Cafe marks halfway to the Pacific – pie included. For 2026, the Texas Festival promises ten days of chrome and chili. Crash at the Big Texan Steak Ranch, where 72-ounce steaks are free… if you finish.
New Mexico: Turquoise Trails and Neon Nights (Days 9-10, ~400 miles)
Tucumcari to Albuquerque
Enter the Land of Enchantment via the quirky Devil’s Rope Museum in McLean (barbed wire hall of fame). Tucumcari’s Blue Swallow Motel glows with vintage signs – book a room for the full retro immersion. Albuquerque’s Nob Hill neighborhood hums with diners and the Breaking Bad house (pink teddy bear optional).
Gallup and Beyond
Gallup’s Navajo Code Talkers Park honors WWII heroes. Detour to Acoma Pueblo, the “Sky City” atop a 367-foot mesa. New Mexico’s centennial will spotlight indigenous stories with cultural fests.
Arizona: Desert Magic and Holbrook Highlights (Days 11-13, ~500 miles)
Holbrook: The Heart of Arizona’s Route 66
Enter Arizona and head straight to Holbrook, our Route 66 crown jewel and the “Gem of the Desert,” located before Meteor Crater and Seligman on the east-to-west route. Just 30 miles east of Petrified Forest National Park, Holbrook is where the highway’s whimsy meets ancient earth. Check into the Wigwam Motel, those iconic concrete teepees from 1950 – sleep like a chief under starry skies (rates start at $75/night). Nearby, the Navajo County Historical Museum chronicles Harvey Girls, trading posts, and railroad lore in a 1898 courthouse.
Hunt treasures at the Holbrook Rock Shop, stuffed with petrified wood and meteorites – or the Rainbow Rock Shop’s roaring dinosaurs guarding gem displays. Grab a burger at Joe & Aggie’s Cafe, a 1940s staple slinging Navajo tacos since the boomtown days. For views, hit the Old Route 66 Vista Point, overlooking the Painted Desert with a symbolic wrecked car evoking the road’s glory days.
Petrified Forest and Winslow
No Holbrook visit skips Petrified Forest National Park (entrance $30/vehicle), just west of town. Hike the Blue Mesa Trail amid rainbow badlands, or drive the 28-mile loop to Newspaper Rock’s ancient petroglyphs. In 2026, Arizona’s Fun Run will convoy through here, with Holbrook hosting pop-up markets and live country tunes. Next, head to Winslow, just 20 minutes west, for the “Standin’ on the Corner” statue (Eagles fans, unite!). It’s the perfect base for a day hike in Canyon de Chelly.
Meteor Crater to Seligman
Continue west to Meteor Crater, a 50,000-year-old impact site bigger than 20 football fields. Then hit Seligman’s Delgadillo’s Snow Cap Drive-In for shakes with a side of snark.
Flagstaff and Kingman
Flagstaff offers the Lowell Observatory (where Pluto was discovered) and historic lumberjack bars. Arizona’s centennial kicks off with a Roaring Twenties party in Kingman on November 15, 2025 – dress in flapper finery!
California: Pacific Dreams and Pier Parties (Days 14-15, ~300 miles)
Barstow to Victorville
The final push! Barstow’s Route 66 Mother Road Museum maps the whole shebang. Amboy’s Roy’s Motel sign screams mid-century cool against volcanic backdrops. Victorville’s California Route 66 Museum adds Hollywood flair.
Santa Monica Finale
End triumphantly at Santa Monica Pier: Dip your toes in the Pacific at the “End of the Trail” sign, Ferris wheel spinning overhead. California’s 2026 lineup includes coastal drives and contests – think vintage car parades from Barstow to the beach.
Hit the Road – Holbrook Awaits Your Story
As Route 66’s centennial dawns, it’s more than a drive; it’s a pilgrimage to the heart of America. From Chicago’s skyscrapers to Santa Monica’s waves, every mile whispers tales of grit and glory. And in Holbrook, Arizona, you’ll find a chapter all your own – where petrified forests meet paved dreams, and the Mother Road feels like home.