50 Best Things To See On Your Route 66 Road Trip

Rebecca Ahn
26 min readAug 6, 2021

If you’re itching to get out of your pandemic bubble and take a much-needed vacation, I recommend you go have a Route 66 road trip adventure. After all, those of us in the U.S. are still allowed to travel within this country... even if travel abroad is still a bit tricky. And what better road to travel than America’s Mother Road, the legendary Route 66.

Some things are a bit emptier thanks to the pandemic, but everything is still more or less open and eager for you to swing by. (Like really eager. All the Route 66 shop owners are struggling right now. Go support them!)

Here are my top 50 recommendations for the best Route 66 stops, attractions, and hidden treats to see along this epic 2,448 mile expedition. It’s a long list, and as such this is a long article, but it’s worth it if you want it.

Of course, there are well beyond 50 things to see and do on Route 66. Every inch is covered in classic old neon signs, murals, old dilapidated buildings, souvenir shops, beautiful landscapes, and so so many picture opportunities.

You might be overwhelmed. It’s normal. Breathe.

You do not need to see everything on this route. Try to make all the especially cool shit I’ve listed. But even then, don’t panic if you miss something. You’re gonna feel like there are way too many reasons to constantly stop and pull over as you go.

And you will miss some stuff. That’s okay. Just take your time.

This road trip takes way longer than you expect it will. So leave yourself plenty of buffer time to explore and enjoy. Stay safe, pay attention to your surroundings, and wear your damn mask… where it’s still required of course.

ILLINOIS

1. “Begin Sign” — Chicago, IL

We drove the westbound route, so we began our road trip at the historic Route 66 Begin Sign on the corner of East Adams St/Jackson Blvd & South Michigan Ave in Chicago. This is the start of your journey. Check your oil. Check your tire pressure. Buckle your seatbelts. And here we go! (Or if

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Rebecca Ahn

Writer • Wanderer • Warrior | toughcookietravel.comamazon.com/dp/B00F2AK2VKrebeccaahn.com | Sharing stories that empower others to survive and thrive