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Route 66 Adventure - 5 Days

Route 66 Adventure - 5 Days Itinerary

Last updated: 2024 Jun 14

Kicking Off in Chicago

Morning
Start your Route 66 adventure in the Windy City, Chicago. Begin your day with a hearty breakfast at Lou Mitchell's, a classic diner known for its delicious breakfast and historic charm. Afterward, head to Route 66 Starting Point Sign to snap some photos and officially start your journey on the Mother Road.
Afternoon
In the afternoon, visit the Route 66 Hall of Fame and Museum in Pontiac, Illinois. This museum is dedicated to preserving the history and memorabilia of Route 66. Enjoy lunch at Old Log Cabin Inn, a historic restaurant that has been serving travelers since the early days of Route 66.
Evening
Arrive in Springfield, Illinois by evening. Visit the Lincoln Home National Historic Site, where Abraham Lincoln lived before becoming president. For dinner, enjoy some local cuisine at Cozy Dog Drive In, famous for its corn dogs and Route 66 memorabilia.
Bedtime
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Exploring St. Louis

Morning
Start your day with breakfast at City Diner, a retro-style diner offering classic American breakfast options. Then head to the iconic Gateway Arch, which symbolizes the westward expansion of the United States and offers stunning views of St. Louis from its observation deck.
Afternoon
In the afternoon, explore the Museum of Transportation, which features an extensive collection of transportation vehicles including trains, cars, and planes. Have lunch at Sweetie Pie's, known for its soul food and Southern hospitality.
Evening
Spend your evening strolling through The Loop neighborhood in St. Louis, filled with shops, music venues, and restaurants. Enjoy dinner at Blueberry Hill, a landmark restaurant known for its burgers and live music performances.
Bedtime
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Discovering Tulsa

Morning
Begin your day with breakfast at Dilly Diner, offering a variety of breakfast dishes made from scratch. Visit the Tulsa Art Deco Museum, showcasing Tulsa's rich architectural history through exhibits on Art Deco design.
Afternoon
In the afternoon, take a trip to the historic Blue Whale of Catoosa, one of Route 66's most recognizable roadside attractions perfect for photo opportunities. Have lunch at Clanton's Cafe, famous for its chicken-fried steak and homestyle cooking.
Evening
Conclude your day by exploring downtown Tulsa's vibrant arts district known as The Brady Arts District. Enjoy dinner at The Tavern, an upscale pub offering gourmet comfort food and craft cocktails.
Bedtime
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Oklahoma City Delights

Morning
Start your day with a delicious breakfast at Classen Grill, known for its hearty breakfast options and friendly atmosphere. Afterward, visit the National Cowboy & Western Heritage Museum, which showcases an extensive collection of Western art and artifacts, providing a deep dive into the history and culture of the American West.
Afternoon
In the afternoon, explore the Route 66 Park, a beautiful park dedicated to celebrating the history of Route 66. The park features walking trails, a lake, and various Route 66-themed sculptures. For lunch, head to Pops Arcadia, a unique diner and soda ranch offering an extensive selection of sodas from around the world.
Evening
Spend your evening in Bricktown, Oklahoma City's entertainment district. Enjoy dinner at Mickey Mantle's Steakhouse, known for its high-quality steaks and elegant ambiance. After dinner, take a stroll along the Bricktown Canal or catch a live performance at one of the local venues.
Bedtime
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Amarillo Adventures

Morning
Ye Olde Pancake Station is your first stop for breakfast in Amarillo; this local favorite serves up hearty pancakes and classic American breakfast dishes. Then visit the famous Cadillac Ranch, an art installation featuring half-buried Cadillacs that visitors are encouraged to spray paint.
Afternoon
Texas Air & Space Museum is next on your list; this museum offers fascinating exhibits on aviation history and space exploration. For lunch, try The Big Texan Steak Ranch, renowned for its giant steaks and Route 66 charm.
Evening
Amarillo Botanical Gardens provides a peaceful end to your day with its beautiful plant displays and serene walking paths. Enjoy dinner at OHMS Cafe & Bar, offering upscale dining with a menu that features locally sourced ingredients.
Bedtime
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