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Guide to Planning a Route 66 Road Trip

Posted on 27 Jan, 2024 at 01:46 pm - by

Here’s everything you need to know before you plan a Route 66 road trip, as much as it is nostalgic to travel through Route 66, it also holds a historical element, making it an ultimate “symbol of Americana” or the “ Will Rogers Highway”, stretching from the southwest of Chicago to Santa Monica California, from crossing over eight different states to wrapping around 3900 km, which is about 2400 miles, it wraps up the parts of Kansas, Illinois, New Mexico, Texas, Arizona, Missouri & California. Route 66 is known for its designation in 1926, whereas 66 indicates the order of how this highway is designated. Below you can find a guide to planning Route 66 holidays:


Choose a Motor Vehicle Accordingly

There can be a variety of modes of transportation depending on the person, different people choose different ways of traveling through it, a motorbike, a bus, or RV, to travel the Mother Road.

The Motorbike tour will be an experience of its own, riding through the open air jamming to “Get your kicks on Route 66” song will give off some old-school classical vibes while keeping the safety rules in mind, whereas taking a bus tour will give you a bunch of people accompanying you that too with a safer feel.


The Starting Point

The highway starts from Illinois, Chicago by passing Michigan’s E. Adams Street, alongside an adventurous road trip, you might see motels, gas stations, and car repair shops springing up with all sorts of tourist traps, the classic vibe of this road has inspired many books, tv shows and series, so you can see an aesthetic and cultural touch in this trip as well.


Refreshing Spots Alongside Route66

Travelling through such a long route, you might need to plan some exciting and touristy spots, so you might get refreshed along the way. It’s better to pre-plan some attractive spots to visit along the way.

Here’s a little sneak peek into some well-known, touristy, and iconic places you can visit, that this exciting road trip has to offer:


  • Gateway Arch

It is a national park that contains far more than just an arch, the arch is something that has become a source of identification for this park, there is also a museum inside, which is free of cost and provides a detailed exhibition regarding America’s westward development and the unique construction of gateway arch, the museum will keep you occupied until you wait for your ride to the top. If you’re Acro-phobic which means you fear heights, we have got you covered, you can take a walk to the top of Eero-Saarinen Monument, which is a manmade, beautifully designed monument and is known as the world’s tallest monument that gives spectacular views of both sides of the Mississippi, so you can witness the world’s tallest arch.


  • Blue Whale of Catoosa:

It’s a popular tourist attraction en route to RT66, which was built by Hugh Davis to surprise his wife Zelta with a unique anniversary gift because she had an eternal love for whales. It’s a cute yet artsy place to go and sit by a picnic table.


  • Cadillac Ranch:

It is a one-of-a-kind roadside art project, where ten Cadillacs are installed in a row, and the tourists are asked to bring their spray paints to personalize it and give their own unique touch to it, artistic souls will surely love this spot.


  • Santa Monica Pier:

You can either count it as a starting or an ending point of Route 66, It’s a perfect fun-filled spot for tourists looking for some beachy vibes on the road, giving off some rides of Ferris wheel to enjoying a roller coaster with some sweet treats that Soda Foundation offers.


The Best Time to Visit

Planning everything also includes the time, the best time of the year to travel the roads of Chicago and to get along with Route 66 attractions is probably fall or spring, but summer can also be an option.


Pack Smart

Get all your travel essentials ready, considering all sorts of incoming conditions and weather fluctuations, you must prepare yourself to survive through all, as this RT 66 road trip passes by various landmarks, waterways, parks, landscapes, and all sorts of attractive spots, this journey may cover mountains, deserts, going from small town to big cities, from plains to the farmlands, you’ll have a wide variety of landscapes to follow.



With planning comes budget making as well, create a budget that accommodates everything and anything you need along the way, a budget that covers food, lodging, and all sorts of travel experiences. Prepare yourself for some extra, unexpected expenses and do your best research to estimate the costs of everything that is included in your RT66 road trip.


Culinary Adventures Along the Way

Look for some best cuisines on the way as Route 66 offers a dive into the diverse range of eateries, providing regional specialties and bringing cultural values, from classical diner spaces to the local eateries you can munch on your favorites and explore the taste of different cultures through it.

You can enjoy local food along the way, Route 66 offers delightful tastes from Chicago’s deep dish pan pizzas to unique Mexican cuisine and not to forget the unique blend of spices offered by Oklahoma as their barbeques are well known for their taste.


Capture Memories

Don’t forget to capture memories to the fullest, because, alongside the Rt 66 road trip, you may find some cute, artsy, and interesting tourist spots including Blue Whale, Cadillac Ranch, Wigwam Village Motel, Ed Galloway’s Totem Pole Park, Meramec Caverns and many more Route 66 attractions to follow.

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