Route 66 Classic: The Mother Road Adventure
Introduction
Route 66, famously dubbed "The Mother Road," represents the quintessential American road trip experience. This legendary highway stretches 2,448 miles from the bustling streets of Chicago to the sun-soaked shores of Santa Monica, weaving through eight states and countless stories of American dreams. Originally commissioned in 1926, Route 66 served as a lifeline for migrants during the Dust Bowl and later became an iconic symbol of freedom and adventure immortalized in literature, music, and film.
This 14-day journey will take you through America's heartland, showcasing dramatic landscapes from Illinois prairies to Missouri hills, Oklahoma plains, Texas panhandle, New Mexico deserts, Arizona's painted desert, and California's mountains. You'll experience authentic Americana at its finest: classic diners serving mile-high pie, vintage motels with neon signs, quirky roadside attractions, and small towns where time seems to stand still. This isn't just a drive—it's a pilgrimage through American history, culture, and the enduring spirit of the open road.
Day-by-Day Itinerary
Day 1: Chicago, IL to Springfield, IL
Distance: 200 miles | Drive Time: 3.5 hours
Morning (8:00 AM - 12:00 PM)
- Start at Grant Park (41.8781° N, 87.6298° W) - Take your official Route 66 beginning photo at the "Route 66 Begin" sign
- Breakfast: Lou Mitchell's (565 W Jackson Blvd) - A Route 66 institution since 1923, famous for double-yolk eggs and thick-cut bacon
- Stop: Joliet Prison (1125 Collins St, Joliet) - See the famous prison from "The Blues Brothers"
Afternoon (12:00 PM - 6:00 PM)
- Lunch: Dell Rhea's Chicken Basket (645 Joliet Rd, Willowbrook) - Historic Route 66 restaurant serving fried chicken since 1946
- Drive through: Dwight, IL - See the Ambler-Becker Texaco Station (41.0964° N, 88.4259° W)
- Stop: Pontiac, IL - Visit the Route 66 Hall of Fame & Museum (110 W Howard St)
Evening (6:00 PM - 10:00 PM)
- Arrival in Springfield: Check into Historic Route 66 Hotel & Conference Center (625 E Saint Joseph St)
- Dinner: Cozy Dog Drive In (2935 S 6th St) - Birthplace of the corn dog on a stick
- Evening activity: Drive by Abraham Lincoln's Home National Historic Site
Day 2: Springfield, IL to St. Louis, MO
Distance: 100 miles | Drive Time: 2 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Charlie Parker's Diner (700 N Grand Ave E) - Classic diner with homemade biscuits
- Stop: Lincoln's Tomb State Historic Site (1500 Monument Ave)
- Drive: Take old Route 66 through Litchfield, IL
Afternoon (12:00 PM - 6:00 PM)
- Lunch: Ariston Cafe (413 Old Route 66 N, Litchfield, IL) - Operating since 1924
- Cross into Missouri: Stop at Chain of Rocks Bridge (38.7589° N, 90.1784° W)
- Arrival in St. Louis: Gateway Arch National Park visit
Evening (6:00 PM - 10:00 PM)
- Hotel: The Chase Park Plaza (212 N Kingshighway Blvd)
- Dinner: Ted Drewes Frozen Custard (6726 Chippewa St) - St. Louis institution since 1929
- Evening: Explore the Delmar Loop entertainment district
Day 3: St. Louis, MO to Springfield, MO
Distance: 220 miles | Drive Time: 4 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Crown Candy Kitchen (1401 St Louis Ave) - Historic confectionery and diner
- Stop: Meramec Caverns (1135 Hwy W, Sullivan, MO) - Famous Route 66 cave attraction
Afternoon (12:00 PM - 6:00 PM)
- Lunch: Missouri Hick BBQ (913 S Bishop Ave, Rolla, MO)
- Stop: Devil's Elbow (37.8414° N, 92.0515° W) - Historic Route 66 curves and Elbow Inn
- Drive through: Lebanon, MO - See Munger Moss Motel sign
Evening (6:00 PM - 10:00 PM)
- Hotel: Route 66 Rail Haven (203 S Glenstone Ave, Springfield, MO)
- Dinner: Lamberts Cafe (1800 W J St, Ozark, MO) - "Home of Throwed Rolls"
Day 4: Springfield, MO to Tulsa, OK
Distance: 200 miles | Drive Time: 3.5 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Gailey's Breakfast Cafe (1800 W Sunshine St)
- Stop: Carthage, MO - Precious Moments Chapel (4321 S Chapel Rd)
- Cross into Kansas: Brief drive through Kansas (only 13 miles of Route 66)
Afternoon (12:00 PM - 6:00 PM)
- Stop: Galena, KS - Cars on the Route (119 N Main St) - Inspiration for Pixar's "Cars"
- Cross into Oklahoma
- Lunch: Nelson's Old Riverton Store (7109 SE Hwy 66, Riverton, KS)
Evening (6:00 PM - 10:00 PM)
- Hotel: Campbell Hotel (2636 E 11th St, Tulsa, OK)
- Dinner: Nelson's Buffeteria (514 S Boston Ave) - Art Deco cafeteria since 1929
- Evening: Walk through Tulsa's Brady Arts District
Day 5: Tulsa, OK to Oklahoma City, OK
Distance: 110 miles | Drive Time: 2 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Brookshire Brothers (Multiple locations)
- Stop: Catoosa Blue Whale (2680 N Hwy 66, Catoosa, OK) - Iconic roadside attraction
- Stop: Chandler, OK - Lincoln Motel (740 E 1st St) - Classic neon sign
Afternoon (12:00 PM - 6:00 PM)
- Lunch: Pop's (660 W Hwy 66, Arcadia, OK) - Modern Route 66 stop with 700+ soda varieties
- Stop: Round Barn (107 E Hwy 66, Arcadia, OK)
- Arrive Oklahoma City: Visit National Cowboy & Western Heritage Museum
Evening (6:00 PM - 10:00 PM)
- Hotel: Ambassador Hotel Tulsa (1324 S Main St) - Historic boutique hotel
- Dinner: Cattlemen's Steakhouse (1309 S Agnew Ave) - Stockyard steakhouse since 1910
Day 6: Oklahoma City, OK to Amarillo, TX
Distance: 260 miles | Drive Time: 4 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Ann's Chicken Fry House (4106 NW 39th St)
- Stop: Oklahoma Route 66 Museum (2229 W Gary Blvd, Clinton, OK)
- Cross into Texas
Afternoon (12:00 PM - 6:00 PM)
- Stop: Shamrock, TX - U-Drop Inn (400 N Main St) - Art Deco gas station
- Lunch: Big Texan Steak Ranch (7701 E Interstate 40, Amarillo, TX) - Home of the 72oz steak challenge
- Stop: Cadillac Ranch (35.1872° N, 101.9870° W) - Iconic art installation
Evening (6:00 PM - 10:00 PM)
- Hotel: Big Texan Motel (7701 E Interstate 40)
- Dinner: Return to Big Texan if you didn't eat there for lunch, or try Yellow City Street Food (2708 SW 6th Ave)
Day 7: Amarillo, TX to Tucumcari, NM
Distance: 180 miles | Drive Time: 3 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Golden Light Cafe (2906 SW 6th Ave)
- Stop: Adrian, TX - Midpoint Cafe (305 W Vega Blvd) - Geographic midpoint of Route 66
- Cross into New Mexico
Afternoon (12:00 PM - 6:00 PM)
- Drive through: Glenrio, TX/NM - Ghost town straddling state line
- Lunch: Route 66 Restaurant (1202 E Route 66 Blvd, Tucumcari, NM)
- Stop: Tucumcari - Drive Neon Row and see vintage motel signs
Evening (6:00 PM - 10:00 PM)
- Hotel: Blue Swallow Motel (815 E Route 66 Blvd) - Iconic neon sign motel since 1939
- Dinner: Del's Restaurant (1202 E Route 66 Blvd)
Day 8: Tucumcari, NM to Santa Fe, NM
Distance: 120 miles | Drive Time: 2.5 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Kix on 66 (1102 E Route 66 Blvd)
- Stop: Santa Rosa, NM - Blue Hole (1085 Blue Hole Rd) - Natural swimming hole
- Drive: Take the "Santa Fe Loop" - Route 66 diverted through Santa Fe from 1926-1937
Afternoon (12:00 PM - 6:00 PM)
- Arrival in Santa Fe: Explore Santa Fe Plaza (35.6870° N, 105.9378° W)
- Lunch: The Shed (113 1/2 E Palace Ave) - Famous for red chile
- Visit: Palace of the Governors and Loretto Chapel
Evening (6:00 PM - 10:00 PM)
- Hotel: La Fonda on the Plaza (100 E San Francisco St)
- Dinner: Tomasita's (500 S Guadalupe St) - New Mexican cuisine
- Evening: Stroll Canyon Road art galleries
Day 9: Santa Fe, NM to Albuquerque, NM
Distance: 65 miles | Drive Time: 1 hour
Morning (8:00 AM - 12:00 PM)
- Breakfast: Cafe Pasqual's (121 Don Gaspar Ave)
- Scenic drive: Take the Turquoise Trail (Highway 14) to Albuquerque
- Stop: Madrid, NM - Ghost town turned artist community
Afternoon (12:00 PM - 6:00 PM)
- Arrival in Albuquerque
- Lunch: Sadie's of New Mexico (6230 4th St NW) - Famous for sopaipillas
- Visit: Old Town Albuquerque (35.0945° N, 106.6703° W)
Evening (6:00 PM - 10:00 PM)
- Hotel: Hotel Andaluz (125 2nd St NW) - Historic boutique hotel
- Dinner: El Pinto (10500 4th St NW) - Historic hacienda restaurant
- Optional: Sandia Peak Tramway for sunset views
Day 10: Albuquerque, NM to Gallup, NM
Distance: 140 miles | Drive Time: 2.5 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: The Grove Cafe & Market (600 Central Ave SE)
- Stop: Acoma Pueblo (35.0133° N, 107.5775° W) - "Sky City" mesa-top pueblo
- Drive: Historic Route 66 alignment
Afternoon (12:00 PM - 6:00 PM)
- Stop: Grants, NM - New Mexico Mining Museum
- Lunch: Monte Carlo Restaurant (721 W Santa Fe Ave, Grants, NM)
- Arrival in Gallup: "Indian Capital of the World"
Evening (6:00 PM - 10:00 PM)
- Hotel: El Rancho Hotel (1000 E Route 66) - Where movie stars stayed, "Home of Movie Stars"
- Dinner: Earl's Restaurant (1400 E Route 66) - Family-owned since 1947
- Shop: Trading posts on Route 66 for Native American crafts
Day 11: Gallup, NM to Flagstaff, AZ
Distance: 190 miles | Drive Time: 3.5 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Ranch Kitchen (3001 W Route 66)
- Cross into Arizona
- Stop: Petrified Forest National Park (34.8098° N, 109.8906° W)
Afternoon (12:00 PM - 6:00 PM)
- Stop: Holbrook, AZ - Wigwam Motel (811 W Hopi Dr) - Sleep in concrete teepees
- Stop: Winslow, AZ - Take It Easy Park corner (Kinsley Ave & 2nd St) - Eagles song reference
- Lunch: RelicRoad Brewing Company (117 E 2nd St, Winslow, AZ)
Evening (6:00 PM - 10:00 PM)
- Hotel: Hotel Monte Vista (100 N San Francisco St, Flagstaff)
- Dinner: Black Bart's Saloon (2760 E Butler Ave) - Steakhouse with musical comedy
- Evening: Explore historic downtown Flagstaff
Day 12: Flagstaff, AZ to Seligman, AZ to Kingman, AZ
Distance: 150 miles | Drive Time: 3 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: The Northern Pineapple Company (14 N San Francisco St)
- Optional detour: Grand Canyon South Rim (1.5 hours each way)
- Drive: Williams, AZ - "Gateway to the Grand Canyon"
Afternoon (12:00 PM - 6:00 PM)
- Stop: Seligman, AZ - Historic Route 66 General Store (22265 N Route 66)
- Lunch: Delgadillo's Snow Cap Drive-In (301 E Chino St, Seligman) - Quirky burger joint
- Drive: Original Route 66 alignment through desert
Evening (6:00 PM - 10:00 PM)
- Hotel: Historic Brunswick Hotel (315 E Andy Devine Ave, Kingman)
- Dinner: Mr. D'z Route 66 Diner (105 E Andy Devine Ave) - Classic 1950s diner
- Visit: Mohave Museum of History and Arts
Day 13: Kingman, AZ to Barstow, CA
Distance: 170 miles | Drive Time: 3 hours
Morning (8:00 AM - 12:00 PM)
- Breakfast: Rutherford's 66 Family Diner (2011 E Andy Devine Ave)