Route 66 Pit Stops | Shelter Insurance®

Route 66 Pit Stops


People say life is a highway…but there are some pit stops that you should add to your bucket list when you take the good old Route 66. If you are a foodie who loves historical sites and iconic landmarks, this might be the map you’d want to follow.

‘Begin' your trip from the start of Main Street of America by visiting the Begin sign in Chicago. The sign has been up since 1923 and although there have been many discussions on where Route 66 begins, the Chicago Department of Transportation decided to put it on East Adams Street where you can start your fun journey. You might want to consider spending a few extra hours in Chicago to check out some other iconic attractions such as the Route 66 Hall of Fame Museum and the Buckingham Fountain.

Once you are ready to hit the road, your next stop is St. Louis, Missouri. Just like in Chicago, there are many attractions worth seeing. If you only have time to see one thing, the Gateway Arch should be your pick. The monument will lift you 630 feet above the ground and give you a 30-mile radius of an amazing St. Louis view.

If heights are not your thing, your next stop in Oklahoma might suit you better. The Ed Galloway’s Totem Pole Park in Foyil, Oklahoma is 3.5 miles away from Route 66. It is the oldest and largest folk art that Oklahoma has to offer. Before you move on to the next state, grab some to-go lunch and have a picnic at the most popular attraction the old road can offer, The Blue Whale. You can enjoy your meal on the picnic tables around the open mouth of the whale.

Once you get back on the road and drive a while, it’ll be dinner time in Texas. Perfect timing for the Big Texas Steak Ranch where you can eat a 72 oz. steak for free when you enter their steak-eating challenge. When you wake up in the morning from the food coma, stop by the world’s only Cadillac Ranch. The attraction has 10 graffiti-covered Cadillacs buried nose-down in the field.

If sculptures aren’t your thing and you want to see more of nature, Sandia Peak Tramway in New Mexico might interest you. It is an aerial tramway that will take you 10,300 feet above sea level. Prepare yourself for a breathtaking view and fresh air. Finish up your day with a walk around the oldest state capital city in America, Santa Fe.

As you wrap up your trip and head into Arizona, stop by the Wigwam Motel. It is also known as the Wigwam Villages. This is not your usual motel–the rooms are built in the form of teepees. The historic motel was built in 1937 and is a great way to go back in history and rest before your final stop, the Santa Monica pier in California. Enjoy the beach during the day and their amusement park at night. It is a great way to end your trip with a bang.

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