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5 Days Exploring Route 66 Itinerary

Last updated: 2024 Jun 14

Chicago to St Louis Highlights

Morning

Start your journey in Chicago with a hearty breakfast at Lou Mitchell's, a classic Route 66 diner known for its delicious pancakes and friendly atmosphere. After breakfast, visit the iconic Route 66 Begin sign for a photo opportunity.

Afternoon

Drive towards St. Louis and stop at the Old Chain of Rocks Bridge, an iconic piece of Route 66 history. Enjoy lunch at the nearby Crown Candy Kitchen, famous for its BLTs and old-fashioned malts.

Evening

Arrive in St. Louis and have dinner at Blueberry Hill, a landmark restaurant filled with pop culture memorabilia. Spend the evening exploring The Loop, a vibrant entertainment district.

Bedtime

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St Louis to Springfield Adventures

Morning

Start your day with breakfast at Southwest Diner in St. Louis, known for its Southwestern-inspired dishes. Then visit the Gateway Arch for stunning views of the city and Mississippi River.

Afternoon

Drive towards Springfield and stop at Meramec Caverns for an underground adventure. Have lunch at Missouri Hick Bar-B-Q in Cuba, MO, known for its smoked meats.

Evening

Arrive in Springfield and dine at Lambert's Cafe, home of the 'throwed rolls.' Spend your evening exploring downtown Springfield or relaxing at your hotel.

Bedtime

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Springfield to Tulsa Treasures

Morning

Enjoy breakfast at Gailey's Breakfast Cafe in Springfield before hitting the road. Visit Fantastic Caverns on your way out of town for a unique drive-through cave tour.

Afternoon

Continue towards Tulsa with a stop in Carthage to see the historic Boots Court Motel. Have lunch at Red Oak II, an open-air museum featuring restored buildings from Missouri's past.

Evening

Arrive in Tulsa and have dinner at The Chalkboard Restaurant located inside The Ambassador Hotel. Explore downtown Tulsa's Art Deco architecture or catch live music in the Brady Arts District.

Bedtime

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Tulsa to Amarillo Discoveries

Morning

Start your day with breakfast at Tally's Good Food Cafe in Tulsa before heading out. Stop by the Blue Whale of Catoosa for a quirky photo op on your way out of town.

Afternoon

Drive through Oklahoma City and visit the National Cowboy & Western Heritage Museum. Have lunch at Cattlemen's Steakhouse in Stockyards City, famous for its steaks and cowboy atmosphere.

Evening

Arrive in Amarillo and dine at The Big Texan Steak Ranch, known for its 72 oz steak challenge. Spend your evening exploring Cadillac Ranch or relaxing after a long day's drive.

Bedtime

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Amarillo to Santa Fe Sights

Morning

Begin your day with breakfast at Ye Olde Pancake Station in Amarillo before hitting the road. Stop by Midpoint Cafe in Adrian, TX – halfway point on Route 66 – for some pie.

Afternoon

Continue towards Santa Fe with a stop in Tucumcari to see its famous murals and neon signs. Have lunch at Del's Restaurant known for its New Mexican cuisine.

Evening

Arrive in Santa Fe and enjoy dinner at The Shed, renowned for its traditional New Mexican dishes like red chile enchiladas. Spend your evening exploring Santa Fe Plaza or visiting local art galleries.

Bedtime

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