Take an iconic road trip along route 66 in the United States

For decades, the idea of road tripping on Route 66 has conjured up images of convertibles with the driver’s hair flying in the wind and wide open roads taking you to something exciting and unknown—and for years, that’s exactly how Route 66 was used. To this day, the highway persists as an idea of freedom and adventure for people who live in America, but also for travellers who are only in the states for a little while. After all, with so many states and attractions to see, what better way is there, than to drive across the country and stop whenever something catches your eye ('World’s Biggest Ball of Yarn, anyone?).

Beyond being a highway that literally crosses the country, Route 66 also acts as a way for people to enjoy the 'fly-over states' that would otherwise get passed over in favour of spots like Los Angeles and New York City. While those places are great, there is something special about connecting with all of America, not just its super-star cities.

This famous highway was built in the 1920’s and it runs horizontally across the country, from the mid-west to the West Coast. The sights will differ and so will the terrain; from mountains to stretches of desert Route 66 is a fun road to travel.

What to Bring

When driving down the Main Street of America, you are going to see many exciting and eclectic landmarks and attractions, so you won’t want to forget your camera with plenty of memory cards to capture every detail of your trip. You may also want to bring along a travel journal to write down all of the memories, save ticket stubs or receipts, and draw your experiences. There’s nothing that jogs your memory faster than looking back at entries you scribbled yourself.

Also, remember that while the road can be fun, it can also be tiring. Take turns driving, stop when you need to, and always keep your eye on the gas metre—no one wants to get stranded in the middle of nowhere because of an empty tank.

Beyond being physically tiring, all that exploring and driving will work up an appetite. Don’t forget to stock up with some healthy snacks and drinks for your trip. You can start the trip with supplies, but you can also stop at any supermarket along the way to refresh your stock of snacks.

What to See

Sears Tower

Renamed the Willis Tower (but still commonly referred to as its original name the Sears Tower), this skyscraper in Chicago is 108 stories tall and held the title of world’s tallest building for 25 years. You can head out onto the observation deck and take in the views of the city. Once you’ve gotten your fill visually, head to downtown Chicago to try one of their famous Chicago-style deep dish pizzas to get your fill, food-wise.

Gateway Arch

Head over to St. Louis to get a view of their famous landmark, the Gateway Arch. This 630-foot monument holds three titles of the world’s tallest arch, the tallest monument in the western hemisphere, and Missouri’s tallest accessible building. After you visit the monument, try out the city’s famous thin crust style pizza and the now famous and always delectable butter cake.


This western state is home to many interesting and unique spots like the world’s largest concrete totem pole near Foyil, Oklahoma and the National Cowboy & Western Heritage Museum in Oklahoma City. These two are a nod to America’s beginnings when the country was first being discovered and development was booming across the western half of the United States.

Texan Food

Texas is known for doing everything bigger: big hair, big hats, big houses, you catch the drift. So when it comes to food, of course Texas is going to do it bigger. Down in Amarillo, the Big Texan restaurant is famous for their gargantuan 72 ounce steak. Strap on a bib and grab some steak sauce and live like a Texan—if only for an hour.

California Living

As you near the end of Route 66, you’ll be able to stop at more sites where the traditions and culture of Native Americans exist. The Mojave Nation preserve is located in Nipton, California along the Route and will give you culturally enriching insight into the people that are native to this country.

Drive through the amazing sights of San Fransisco and Wine Country, USA and make your way down to Los Angeles. The end of the road, quite literally, is the Santa Monica Pier. This famous pier, which dips its toes into the Pacific Ocean, will serve as a perfect spot to celebrate your accomplishment of finishing Route 66. Get out of the car and see L.A. like a local. The Pier has food, fun, and entertainment.

When you plan a road trip, you can get your car checked out, you can prep to have everything you’ll need, but there is always a chance that something will go wrong on the road—especially if you are renting a car at your destination. Consider the benefits of rental car insurance cover and compare plans to make sure if you get stuck by the side of the road, you’ll have someone sending help for you as soon as possible.

Image courtesy of Flickr user Tony Hisgett