The 4 Most Iconic US Road Trips


Written by Shannon O’Donnell on

Shannon O'Donnell is a long-term traveler who has been on the road since 2008 and has lived everywhere from Southeast Asia to Barcelona, where she now calls home. She travels slowly and supports responsible tourism along the way, winning numerous awards for her work advocating for the communities impacted by travel and tourism.



The U.S. road trip is part of the fabric of Americana. From Hawaii to the start of Route 66 in Chicago, from the cliffs of the PCH to the gates of Yellowstone National Park, these four parks exemplify the best of American car travel and make perfect road trip destinations.


The great American road trip—is there anything more classic? Packing up the car, making themed playlists, loading up on travel snacks … exploring the country from behind the wheel is part of the fabric of Americana. The following are some of the great US road trips, in terms of iconic highways, amazing sights, and the potential for experiences you’ll never forget.


1. Route 66

Get your kicks! The “mother road” of America—which has been immortalized in art, cinema, and song—wends its mighty way through six states’ worth of quaint off-ramp towns between Chicago and Santa Monica. Clocking in at an astounding 2,600 miles, there’s no better place to get lost in plain sight. Plan on lots of stops for corny roadside attractions … the world’s largest ball of twine, anyone?

Road Trip Tip: The traditional way to travel Route 66 is a 12-day itinerary, which works out to less than five hours on the road per day and leaves plenty of time to explore. Staying organized is key when you’re elbow-to-elbow in a cramped car.


2. Beartooth Highway

Late broadcasting personality Charles Kuralt called this 68-mile stretch the most beautiful road in America, and you will have to see it for yourself to decide. Stretching from the end of Yellowstone National Park by way of 10,947-foot Beartooth Pass between Cooke City and Red Lodge, Montana, going in and out of Wyoming en route, expect breathtaking vistas and Insta-worthy pic opportunities along your road trip route.

Road Trip Tip : Beartooth Highway is only open to traffic in the summer. Perfect for a daytrip, a light bag like the Wayfinder 20L will work perfectly for a change of clothes and some snacks.


3. Pacific Coast Highway (PCH)

You’ll be California dreamin’—only if you’re a passenger, of course—against the backdrop of the crashing Pacific Ocean as you cruise possibly the most sung-about American highway. The PCH  extends from San Francisco down a chilling, thrilling, 123-mile span along the cliffside. Small beach towns like Cambria and Monterey have sleepy, chill vibes and all-but-deserted beaches where you’ll have the silky sand all to yourself when you drive this iconic route. Given the proximity of the ocean, this is one of the best options for family road trippers.

Road Trip Tip : A can’t-miss photo op is the record-setting concrete behemoth that is the Bixby Bridge in Big Sur. Slip your phone and a spare charging pack into a slim cross-body that’s effortless to snap on and go.


4. Hana Highway

Hawaii is full of lush tropical scenery, the best of which is on full display during the deceptively short drive from Kahului to Hana, a tiny seaside town on eastern Maui. Fifty-two miles may not seem like a lot, but the snaking roadway and steep cliffside will definitely earn you that touristy “I Survived the Road to Hana!” t-shirt at the gift store. The juice is definitely worth the squeeze in this case, as the winding highway will take you by blooming stands of fragrant mango trees, ramshackle roadside stands hawking the best homemade banana bread you’ve ever tasted, and the constant, timeless churn of the ocean below. On Hana itself, unabashed nude sunbathers bask in close proximity to lowing lion seals. And Hawaii has great hiking too—you’ll have some of the best hikes in the world on your doorstep.

Road Trip Tip: You’ll have to journey the last distance on foot, as the road is “unpassable,” but it’s worth strapping on your hiking shoes to visit the Seven Sacred Pools, a gently cascading, seven-tiered gulch at Haleakala National Park. A lightweight duffel will carry an afternoon’s worth of supplies, including all your swimming and photography gear.


Are you preparing for your own American summer road trip? Find out what you should and shouldn’t pack to take advantage of limited space without sacrificing any comfort.


Related Links (from the Eagle Creek blog):

How to Stay Organized on a Road Trip

10 Road Trip Essentials You Should Always Pack

How To Plan and Execute a Cross-Country Road Trip