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Route 66 Adventure - 5 Days

Route 66 Adventure - 5 Days Itinerary

Last updated: 2024 Jun 14

Kickoff in Chicago

Morning
Start your Route 66 adventure in the Windy City, Chicago. Begin with a visit to the iconic 'Begin Route 66' sign located at East Adams Street. This is a must-see spot for every Route 66 traveler and a perfect photo opportunity to mark the start of your journey. Afterward, take a stroll through Grant Park and enjoy the beautiful views of Lake Michigan and the city skyline. For breakfast, head to Lou Mitchell's, a historic diner known for its hearty meals and welcoming atmosphere.
Afternoon
In the afternoon, dive into some local culture by visiting the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore its vast collection of artworks from different periods and regions. After soaking in some art, take a short walk to Millennium Park to see Cloud Gate (The Bean) and Crown Fountain. For lunch, enjoy some deep-dish pizza at Giordano's, an iconic Chicago eatery.
Evening
As evening approaches, make your way to Navy Pier for some entertainment and relaxation by Lake Michigan. Enjoy rides, games, and live performances while taking in stunning views of the city skyline at sunset. Don't miss out on trying some delicious seafood at Riva Crabhouse on Navy Pier before heading back to your accommodation.
Bedtime
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Exploring Springfield

Morning
Depart from Chicago early in the morning and head towards Springfield, Illinois (approximate travel time: 3 hours). Upon arrival, start your day with Springfield Scavenger Hunt, an exciting activity that will help you discover hidden gems around this historic city while having fun solving clues. For breakfast or brunch before starting your scavenger hunt adventure, visit Darcy's Pint, known for its famous horseshoe sandwiches.
Afternoon
After completing your scavenger hunt adventure in Springfield's downtown area filled with historical landmarks related to Abraham Lincoln such as his home site or presidential library/museum; spend some time exploring these significant sites more deeply if they caught interest during hunt! Have lunch at Cozy Dog Drive In, where you can try their original corn dogs which are said be invented here! This place has been serving travelers since 1949 making it true piece Americana history itself!
Evening
In evening unwind by visiting Lincoln Memorial Garden & Nature Center located along shores Lake Springfield offering peaceful trails amidst natural beauty perfect way end busy day sightseeing historical places earlier part day! Enjoy dinner nearby at Obed & Isaac's Microbrewery offering variety craft beers brewed on-site paired delicious pub fare making great spot relax before heading back hotel rest up next leg journey tomorrow!
Bedtime
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Stunning St Louis

Morning
Leave Springfield early morning drive approximately two hours reach St Louis Missouri known Gateway Arch symbolizing westward expansion United States Begin day visiting this iconic monument taking tram ride top breathtaking views Mississippi River surrounding areas Afterwards explore nearby Museum Westward Expansion learn about history pioneers who traveled across country settle new lands Breakfast suggestion would be Rooster popular brunch spot serving creative dishes locally sourced ingredients
Afternoon
Spend afternoon Forest Park one largest urban parks America home many attractions including Saint Louis Zoo Art Museum Science Center History Museum Take leisurely stroll through park enjoying lush greenery beautiful landscapes Alternatively choose specific attraction within park spend more time exploring depth example visiting world-renowned zoo free admission offers chance see wide variety animals habitats Lunch recommendation would be Pappy's Smokehouse famous its mouthwatering barbecue ribs pulled pork sandwiches
Evening
Conclude day lively Delmar Loop entertainment district filled unique shops restaurants live music venues Catch show Blueberry Hill legendary venue where Chuck Berry performed regularly Dine nearby at Pi Pizzeria known its deep-dish pizzas thin crust options made fresh ingredients perfect way wrap up exciting day St Louis
Bedtime
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Charming Tulsa

Morning
Start your day with a visit to the Philbrook Museum of Art, housed in a beautiful Italian Renaissance villa surrounded by lush gardens. This museum features an impressive collection of art from around the world, including Native American and contemporary works. For breakfast, enjoy a delicious meal at Dilly Diner, known for its farm-to-table dishes and cozy atmosphere.
Afternoon
After exploring the museum, head to the Tulsa Arts District for an afternoon of culture and creativity. Visit the Woody Guthrie Center to learn about the life and legacy of this iconic American folk musician. Then, take a stroll through the district's galleries, shops, and public art installations. For lunch, stop by Laffa Medi-Eastern Restaurant & Bar for some flavorful Mediterranean cuisine.
Evening
Springfield Scavenger Hunt - Continue your scavenger hunt adventure in Tulsa's vibrant downtown area. Discover hidden gems and historical landmarks while solving clues and challenges. Afterward, unwind with dinner at Tavolo, an Italian bistro offering delicious pasta dishes and a warm ambiance.
Bedtime
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Oklahoma City Highlights

Morning
Springfield Scavenger Hunt - Begin your day with another exciting scavenger hunt experience in Oklahoma City's Bricktown District. Explore this lively area filled with entertainment venues, restaurants, and shops while solving clues along the way. For breakfast or brunch before starting your scavenger hunt adventure, visit Bricktown Brewery, known for its hearty meals and craft beers.
Afternoon
After completing your scavenger hunt adventure in Bricktown; spend some time exploring other attractions such as Myriad Botanical Gardens offering beautiful landscapes walking trails perfect place relax after busy morning! Have lunch nearby at Cattlemen's Steakhouse famous its mouthwatering steaks western-style dishes making great spot refuel before continuing exploration city!
Evening
Springfield Scavenger Hunt - Conclude your day with another round of scavenger hunting fun in Oklahoma City's downtown area discovering more hidden gems historical sites along way! Enjoy dinner at Mickey Mantle's Steakhouse upscale restaurant offering variety delicious dishes elegant setting perfect way wrap up exciting day Oklahoma City!
Bedtime
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