Road Trip Guide
Route 66: The Great American Mother Road
Chicago, IL to Santa Monica, CA
Start Your Engine
Chicago, IL
The Finish Line
Santa Monica, CA
Approximately 2,448 miles
Miles
14-21 days (for a comprehensive experience)
Days
Start Stops End
Trip Essentials for Chicago, IL
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Insider Driving Tips
**Plan, but be Flexible:** While it's good to have a general itinerary, allow for spontaneous detours. Many of Route 66's best gems are found unexpectedly off the beaten path.
**Invest in a Good Map/Guidebook:** GPS is great, but signals can be spotty in rural areas. A physical map or a dedicated Route 66 guidebook will be invaluable for navigating historic alignments.
**Support Local Businesses:** Many of the diners, motels, and shops along Route 66 are family-owned and have been for generations. Your patronage helps keep the spirit of the Mother Road alive.
**Embrace the Kitsch:** Don't be shy about stopping at every giant Muffler Man, quirky museum, or vintage souvenir shop. These eccentricities are part of what makes Route 66 so special and memorable.
**Capture Everything:** Bring a good camera (and plenty of storage!). From neon signs to vast desert landscapes, Route 66 offers endless photographic opportunities. Don't forget to get in the frame yourself!
The Journey: Stop-by-Stop
Springfield, IL
Cozy Dog Drive In
“Home of the original 'hot dog on a stick' (predating the corn dog), this iconic diner has been serving Route 66 travelers since 1946. Step inside for a delicious, no-frills meal and soak in the classic diner atmosphere, complete with vintage decor and friendly service.”
Lincoln Home National Historic Site
Capture the beautifully preserved 19th-century neighborhood surrounding Abraham Lincoln's only owned home. The street itself, with its period lamp posts and brick sidewalks, offers a timeless backdrop.
Illinois State Capitol Building
The majestic dome and intricate architecture of the Illinois State Capitol provide a stunning backdrop, especially when photographed from the surrounding park grounds, reflecting its grandeur.
Shea's Gas Station Museum
A truly unique and heartfelt tribute to Route 66, this privately owned gas station museum is packed with vintage pumps, signs, and memorabilia. Owner Bill Shea loved sharing stories about the Mother Road, making it a personal and authentic experience, often described as stepping back in time to the golden age of motoring.
St. Louis, MO
Ted Drewes Frozen Custard
“A St. Louis institution since 1929, Ted Drewes serves incredibly rich and creamy frozen custard. Be sure to try a 'concrete,' a super-thick shake that can be held upside down without spilling. It's a perfect, nostalgic Route 66 treat.”
Gateway Arch National Park
Capture the awe-inspiring stainless steel arch from various angles, reflecting the sky and the city skyline. The reflection pools at its base offer particularly striking photographic opportunities.
Old Chain of Rocks Bridge
Standing majestically over the Mississippi River, this historic bridge (now pedestrian-only) offers panoramic views and a unique 22-degree bend in the middle, creating a dramatic perspective for landscape shots.
City Museum
More an adult playground than a museum, this eclectic attraction is built from repurposed architectural and industrial objects. Explore caves, climb through tunnels, slide down ten-story chutes, and discover a truly unique, imaginative experience unlike anything else.
Oklahoma City, OK
Nic's Grill
“A tiny, unassuming diner famous for its legendary burgers. Be prepared for a wait, as locals and travelers alike flock here for one of the best, juiciest, made-to-order burgers you'll ever taste. It's a true hidden culinary gem.”
Oklahoma City National Memorial & Museum
The reflective pool, empty chairs, and the 'Gates of Time' offer powerful, evocative photographic opportunities that convey solemnity and remembrance. Focus on the interplay of light and shadow at dawn or dusk.
Bricktown Canal
Capture the vibrant atmosphere of the revitalized Bricktown entertainment district with its charming canal, water taxis, and historic brick buildings. Evening shots with the lights reflecting on the water are particularly stunning.
The Gold Dome
A unique architectural marvel, The Gold Dome is a geodesic dome structure built in 1958. Originally a bank, its futuristic design and golden sheen make it a fascinating, often overlooked, piece of Route 66 history and mid-century modern architecture.
Amarillo, TX
The Big Texan Steak Ranch
“Famous for its 72oz steak challenge (free if you can eat it all in an hour!), this legendary steakhouse is a Route 66 icon. Even if you don't take the challenge, the atmosphere, live music, and generous portions make it a must-visit.”
Cadillac Ranch
Photograph the ten iconic, graffiti-covered Cadillac cars buried nose-down in the Texas dirt. Capture the ever-changing art, the vast sky, and visitors adding their own spray paint to this famous art installation.
Route 66 Historic District (Sixth Street)
Stroll and photograph the vibrant stretch of historic Route 66 on Sixth Street, featuring beautifully preserved neon signs, vintage storefronts, and classic cars, especially stunning at dusk.
Jack Sisemore Traveland RV Museum
A fantastic, free museum showcasing an incredible collection of vintage RVs, travel trailers, and motorcycles. It's a nostalgic trip back in time, offering a glimpse into the evolution of road tripping and American leisure.
Seligman, AZ
Roadkill Cafe
“Embrace the humor and kitsch of Route 66 at this uniquely themed cafe. While they don't actually serve roadkill, their classic American diner fare comes with a playful menu and a lively atmosphere that perfectly captures the roadside spirit.”
Historic Route 66 Murals and Neon Signs
Capture the vibrant murals depicting Route 66 history and the iconic, glowing neon signs that light up the main street, especially mesmerizing as twilight descends.
Classic Car Displays on Main Street
Photograph the numerous perfectly preserved classic cars, often parked outside shops and diners, creating a timeless scene that transports you straight into the 1950s.
Angel & Vilma's Original Route 66 Gift Shop
Meet Angel Delgadillo, the 'Guardian Angel of Route 66,' who tirelessly campaigned to preserve the historic highway. His barbershop and gift shop are filled with stories, memorabilia, and the chance to meet a true legend of the Mother Road.
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Frequently Asked Questions
Yes, while much of the original Route 66 has been replaced by interstates, significant and well-preserved stretches remain. You'll need a good map or GPS specifically for 'Historic Route 66' to navigate these sections, as they often run parallel to or diverge from the modern highway.
Spring (April-May) and Fall (September-October) are generally considered the best times. Temperatures are more moderate, making for comfortable driving and exploring. Summer can be extremely hot, especially in the desert states, while winter can bring snow and ice, particularly in the Midwest.