There’s this feeling you have when you realize you’re in a car with someone your own age and no adults for the first time. I remember being a freshman in high school when a senior said he’d drive me home from our cast party after closing night for Inherit The Wind. Being alone in a car — no one’s mom pulled up to the curb outside the party armed with questions like, “Did you girls have fun?” and “Who was there?” and “What did you do?” — was a dizzying level of freedom. All of a sudden, my hazy future was rendered more clearly. I’d get a car of my own one day. Then an apartment. And then…
This heady sensation is eventually eclipsed by your first real road trip. Picking your own route, listening to a playlist you made, eating gas station Funions — this is real living. It’s adulthood and adventure in equal measures, inextricably bound together. My first road trip was just a jaunt to Madison, Wisconsin from small-town Michigan, but I felt like Jack Kerouac. I was a lonely wanderer, out seeking answers along the endlessly unfolding tarmac.
I don’t think I’ve ever lost that initial feeling of freedom and excitement for road trips. Few other types of travel give you that pure “Go where the wind takes you” feeling, even when you have an agenda and Google maps. Hear about a great hike to a hot spring? A restaurant that serves spectacular cherry pie? The world’s largest something or other? You can just pull off the road and your trip will be better for it. Road trips are filled with unexpected destinations. They’re loaded with disasters and laughter and chaos and, eventually, they lead to great stories.
Below you’ll find eight truly iconic American road trip routes. They’re adventures that will teach you about America… and yourself.
The Americana Road Trip — Route 66 — Arizona
It may have been a long time ago, but Route 66 was a big deal. Like, huge. It was called “The Mother Road” and “Main Street of America.” It holds a prominent place in our collective history. It ran from Chicago, the hub of the midwest and an epicenter of the industrial revolution, to Santa Monica, the rowdy western outpost turned glamorous haven for the stars. Over the years, the long decommissioned highway has come to represent a certain era in American history. It stands for the days when communities gathered at the local diner, cars were the ultimate gateway to freedom, and the trip west across the country held endless potential.
Though the road was officially broken up in 1985, there are still some stretches of it that are driveable today. Many, in fact, though they go by different names. Chances are you won’t have the disposable time to drive the whole thing, nor should you, no one needs that much mid-century nostalgia. I recommend driving the road through Arizona, not far from the south rim of the Grand Canyon. Something about the Arizonans, they go all in for the pure American kitsch that Route 66 has come to embody. This is the stretch that John Lasseter and other Disney animation execs traveled to get a feeling for the world of Cars.
Be sure to stop for lots of greasy-as-all-get-out food. This is where a classic burger, onion rings, and chocolate malt taste just like they did back in the 50s. Try Delgadillo’s Snow Cap in Selgman or Mr. D’z Route 66 Diner in Kingman — two places where the roadside diner experience remains virtually unchanged in all the best ways. To work off those calories, visit Havasu Falls on the Havasupai Indian Reservation or… y’know… the Grand Canyon.
Make sure not to miss: The city of Oatman, where wild mules roam the streets. The stories of the old west were tales of automation and technology (via the train network) changing lives for the cowboys and frontiersmen of old. There’s not much from that bygone era left anymore. Mostly it’s just Oatman, a dusty outpost famous for those feral mules, some abandoned mines, and a clapboard saloon that is unironically called “The Glory Hole.”
If that’s not your type of town, we don’t need to plan a road trip together.
Song to play: Get Your Kick on Route 66, Chuck Berry
https://www.youtube.com/watch?v=SJe_WWSDqqY
–Steve Bramucci, Travel Editor, Uproxx
The California Coast Road Trip — Pacific Coast Highway — Los Angeles to San Francisco
This is the kind of road trip where basically anywhere you stop, you can’t go wrong. You’re driving along beaches, cliffs, through lush greenery, and every moment is like an explosion at the postcard factory. It’s the kind of trip where you lean out of the passenger window to take pictures every five minutes, even though you know those pictures are going to turn out stupid or blurry. Ignoring reason, you do it anyway.
There’s a ton to do on this route but a few favorites: I would start with a hike in Los Liones, just north of L.A. where Sunset meets PCH. This is my favorite hike in the city. The first half is moderate, fairly short, and brings you to a stunning view. The next part is brutal and hot and while it will also bring you stunning views, you ought to save it for a full hiking day. After the first half, head down, and jump on the road so you’re not exhausted for the rest of the road trip. Stop for lunch at Malibu Seafood Fresh Fish Market & Patio Cafe, the little roadside place has amazing, fresh seafood with zero frills. You can take your order and go across the street to eat it at the beach. Other potential great stops: Santa Barbara which has an adorable downtown area to eat or shop in, Hearst Castle or Nitt Witt Ridge, and the elephant seal rookery to see a very large number of seals sunning on the beach.
If you can, stay a night in Big Sur, which is truly incredible. A yurt or camping spot in the adults only Treebones Resort has you right on the edge of a cliff with stunning views and is a dream spot to catch the sunset. The next morning, hike and explore as much as time allows, swimming holes and waterfalls abound in Big Sur. Later, continue your travels north. There are several cute towns to stop in before you hit San Francisco, Carmel-by-the-Sea never disappoints.
Make sure not to miss: Hiking to Salmon Creek Falls in Big Sur! The stunning falls and swimming hole are a short hike off the highway — there are some difficult parts, including a one section where you have to navigate balancing on pipes to get across the rocks (it’s a little bit tricky, but if I can do it, the clumsiest person on Earth, I think almost anyone can manage it without much trouble), but the payoff is super worth it.
Song to play: Wouldn’t It Be Nice, The Beach Boys
-AS
The Navajo Country Road Trip — US 163 and US 191 — Monument Valley to Canyon de Chelly
I’ll be dead honest: This is my favorite road trip on earth. The east coast of Australia? The safari parks of Central Africa? The dusy surf trails of Mexico? For me, nothing compares to Navajo Country.
Perhaps the reason I love this trip so much — and to be clear, I’ve taken it five times solo or with girlfriends and even guided a family of tourists on the route once — is because there’s not a ton to it. You won’t get lost, the driving is easy and there are plenty of signs. You won’t piss other drivers off, there aren’t many of them. And you won’t ever feel rushed. This is the slowest, laziest adventure in the country. If you miss sunrise at Monument Valley, you’ll catch it at Mexican Hat. Want a swim? Pull over and take a dip in the San Juan River.
Food and where to camp follow this same pattern. The Swinging Steak is a must stop for meat eaters, but for the most part you’re going to be stopping at the Indian Taco stands alongside the road. Or buying Navajo frybread and eating it throughout the day with peanut butter and jam. Car camping in this region is a breeze but if you want a hotel, well… until you get to Chinle, at the end of the trip, the options are limited. The San Juan Inn is a nice little spot, where the locals are happy to see you. If you want a photo op, pose on the tarmac as you near Monument Valley. This is where Forrest Gump stopped his cross country run in the movie of the same name.
Make sure not to miss: Riding Navajo ponies through Canyon de Chelly. The chance to gallop these horses, which are well cared for by their indigenous owners, through a canyon where the walls are lined with Hopi cliff dwellings is some “once in a lifetime” level stuff. It’s literally unmissable.
You think a road trip feels freeing? Wait until you’re galloping a horse through a shallow creek round about sunset.
Song to play: Against the Wind, Bob Seger & The Silver Bullet Band
-SB
The Montana Parks Road Trip — 191 to 90 to 93 to Going-To-The-Sun-Road — Yellowstone to Glacier
It’s hard to even know where to start with this one. Montana is one of my favorite states in the country and I’ve spent a lot of time road tripping in it. What I love about going from Yellowstone to Glacier is you get two of the prettiest National Parks in the country and you also get two super cool hippie towns in the mountains, Bozeman and Missoula. Plus about a million beautiful places to explore, hike, and adventure in between.
Start in the Wyoming part of Yellowstone and really explore the park. Whenever you’re ready, you’ll want to exit the park in the northwest corner, you can either leave by 191 or 89 and head to Bozeman. 191 will take you through beautiful big sky country, 89 will take you through to visit one of my favorite places on earth, Chico Hot Springs. Bozeman is an awesome town, make sure to go downtown and hit the businesses up. While there, Fairy Lake is one of my favorite hikes — with its crystal clear blue waters. Moving on, take 90 though Missoula (a seriously delightful town I would absolutely live in), and stop to camp by Flathead lake (which is so pretty) before heading into Glacier.
The trip ends with going through Glacier National Park on Going-To-The-Sun Road, which is one of the most beautiful drives you could ever take, period. Waterfalls, glaciers, forest, mountains — I’m about to break into my Stefon voice — this route has it all.
Make sure not to miss: Butte, Montana. Butte is the perfect road trip stop because it’s really cool while also being really weird and slightly creepy (no road trip should avoid the weird). It was one of the richest mining towns in the world at one point in time. And because of this, the town is filled with gorgeous buildings that have this “preserved in time” feel. It’s also home to America’s largest Superfund site and a visit to Berkely pit (formed after the mining operations stopped), brings you to a lake so toxic that once hundreds of geese landed and immediately died there, like something out of a horror film.
There’s a lookout area and it’s… grotesquely pretty?
Song to play: Pink Moon, Nick Drake
-AS
The South Florida Road Trip — US-1 South — Miami to Keywest
This is as easy as a road trip gets. Point your car. Go straight. There’s one road and when it runs out you’ll be surrounded by ocean.
Considering that this is really only a three or four-hour drive, you don’t need a ton of stops. But still, take them. The first time I drove this road, I pulled over at an abandoned lot for a nap on the grass. I said aloud, “It would be cool to see a manatee,” and my girlfriend replied, “I hear they’re not as common as we’d like to think.” Seconds later a colossal manatee began munching the seagrass a few feet from where I was dangling my legs.
On the way into Key West, you absolutely have to stop for at the Islamorada Shrimp Shack. The Guy Fieiri approved restaurant is just the sort of place where you’ll see oddball characters that make a good road trip. Plus the shrimp and conch are delicious.
A little further down the road, after crossing that incredible feat of human engineering, the Seven Mile Bridge, you’ll reach Bahia Honda State Park. This tiny state park just might boast the best beach in America. Powdery white sand, crystalline waters — and with your drive winding down, this is the spot to get in the water before reaching Key West.
Once you get out to Key West, well… you’ll know what to do. There are beaches aplenty. You can snorkel or windsurf or ride bikes or maybe just wander around downtown, just like old Papa Hemingway used to.
Make sure not to miss: The Stoned Crab is the best restaurant on the island and perhaps the best in Florida, assuming you like seafood. Order a basket of huge stoned crab claws, which are taken from the crab’s body and later regenerate, creating a truly sustainable fishery. The claw meat, straight out of a crab boil and served with butter, is better than Michelin-starred cuisine any day of the week.
Song to play: Kokomo, The Beach Boys (Stamos version, obviously)
-SB
The Indigenous tour of South Dakota Road Trip — Various — The Badlands to Crazy Horse Memorial
When people ask me what to do on a road trip up through the Dakotas to Montana, my biggest advice is this: Don’t go to Mount Rushmore. There are a few reasons for this, but most of all: it’s a disrespectful place carved on seized land. Our own Zach Johnston wrote a fantastic explainer, but the government not only forcibly took this sacred land from the Lakota but carved faces of their oppressors onto one of their mountains. That’s pretty monstrous. Also — and this is a lesser reason — it’s not a very interesting place to visit. It doesn’t come with an insightful historical museum, it comes with a bunch of disinterested, sweaty tourists taking five minutes of pictures and then wandering into the gift shop where there’s air conditioning so that they can buy magnets. Instead, head straight to Crazy Horse Memorial.
Driving through the Badlands is an insanely cool experience. The first time I drove through, I was blown away by the dry, desolate landscape — there are so many colors to the desert and rocks that it feels like the whole area is one big painting you’ve been dropped inside of. Make sure to do at least one hike so that you can see a panoramic of the area. Notch Trail and Saddle Pass Trail both have amazing views of the area, Saddle Pass is a lot more challenging though, so if you’re looking for something a little more lowkey, effort-wise, you may want to stick with Notch. From there, consider driving a bit south (it’s not directly on the route to Crazy Horse but road trips are never about the straightest fasted line!) to The Heritage Center at Red Cloud Indian School. Located on the south end of Pine Ridge Reservation, it’s a great way to both experience and enjoy yourself, while also giving your tourism money to the people who need it. Pine Ridge historically has (and continues to have) some of the lowest life expectancies among counties in the U.S. The Heritage center has shows from Indigenous artists and is a place to buy trip souvenirs that are created by local artisans. On the way to the Heritage Center, you should definitely stop at Oglala Lakota College Historical Center. It’s a small museum, but a powerful one, that will give you the history of the Lakota and will provide important (and devastating) historical context for your trip to Crazy Horse Memorial.
Continuing on to Crazy Horse Memorial, spend time with the gorgeous sculpture that has been in progress since 1947, with zero funds from the government (they refuse them, choosing to have it funded by the people and not let the government be able to control any part of its vision). Work is slow but continues on. And seeing it — even incomplete — is pretty awe-inspiring.
Make sure not to miss: The Indian Museum of North America, located at Crazy Horse Memorial. Stop by and see its art, history, and learn in more detail about the memorial itself and its goals to preserve cultural traditions and give educational opportunities to Indigenous peoples. Also, grab some food at Laughing Water Restaurant on site. You don’t normally expect delicious food from a museum or memorial cafe, but it’s legit.
Song to play: My People, City Natives
-AS
The L.A. Springtime Desert Road Trip — Various — L.A. to Las Vegas
The amazing thing about L.A. is how many diverse natural landscapes you can get to in just hours from the city. Beaches, sure? Lush forests? Absolutely. Snow-capped mountains? Why not? It’s like someone was designing the world and then at the end just had a bunch of leftover materials and decided to just throw them all into the last place left, but like, in a good way. One of my favorite (and one of the most unique) parts of Southern California, is its desert landscapes. I love going out there, renting an Airbnb with a bunch of friends or camping, and just feeling the vast, creative energy that the desert pumps into you. If you want a trip that really hits some of the highlights of the desert, this loop (eventually ending up with you hitting the City of Sin), checks off a lot of boxes.
From L.A., head east on the ten toward San Bernadino then swing down to Anza-Borrego Desert State Park — this spring they’re expecting a super bloom, don’t you dare miss it. The sea of colorful flowers against the starkness of the desert is incredible. After the one billion pictures you take here, you’ll loop around north, hitting Coachella and Indio before nearing Palm Springs. This would be your day to hit up Palm Springs if you’d like a “party by the pool” desert kind of day. Palm Springs gives you all of those oasis feels.
Spend the day/night at Ace Hotel and Swim Club to experience one of their epic pool parties or, for a more intimate (and ridiculously gorgeous) experience, the Korakia Pensione for the ultimate retreat-type atmosphere with tons of cozy spaces to lounge, soak in the warm pool, sit by the fire, or cuddle the night away. Then head toward Joshua Tree (only a short distance away). There are so many cool things to do in the area, but I love the Noah Purifoy Outdoor Desert Art Museum — which has an insane collection of the artist’s massive found object art. It’s apocalyptic and strange and beautiful all at once, telling the story of racism and oppression in America.
For night time, head to the iconic, Pappy and Harriet’s which often hosts amazing musicians. Finally, (perhaps the next day) head through Joshua Tree park to hike, take a million pictures with the famous tree itself, and then head on to Vegas. After the incredible nature you’ve experienced, you’ve earned some Vegas-style opulence.
Make sure not to miss: If you want to hang your head for the night in Joshua Tree, Hicksville Trailor Palace and Artist’s Retreat has a collection of these super fun vintage trailers and airstreams around a pool to stay in. They’re all lovingly redone and decorated and it’s super kitschy and cool. Just make sure you make a reservation first, the location is secret (they tell you when you book) and if you geotag yourself you’re banned for life.
Song to play: Dancing In The Moonlight, King Harvest
https://youtu.be/hMc8naeeSS8
-AS
The Smoky Mountains Fall Road Trip — 441 (Newfound Gap Road) to 321 — Smoky Mountain National Park to Dollywood
When I was a kid, in the fall, I could stand out on the porch in the mornings, after the fog lifted, that wrapped around our house and look out onto a tapestry of the fall colors as far as the eye could see. In the winter our yard was large and steep enough for a line of kids to go sledding. Behind it, acres of woods to tramp through. If I could distill my memories of Tennessee into one feeling, it would be fall leaves crunching, trees towering above me, the smell of dirt and pine and the quiet peacefulness of it. Like there’s a secret between just you and the mountains that you could hear if you just listened hard enough. The North East corner of Tennessee’s mountains are different from anywhere else in the world. The Smoky Mountains are ancient, worn down into softer curves that its west coast brothers and sisters, gentler, covered in trees and teeming with life. A trip through Smoky Mountain National Park in the fall is one of the prettiest drives you can take!
This is one of the shorter “road trips,” so plan on spending some time just exploring the park! Newfound Gap road will take you from Cherokee, North Carolina straight through the park. It’s a beautiful drive and free — which is a nice bonus. A few things you’ll want to do in the park: Stop at the Newfound Gap lookout for pictures, the views are stunning. For hiking, Chimney Tops is really lovely and a great wildflower hike — just know this has steep elevation and you want to be in relatively good shape to do it and Clingman’s Dome — which is a short hike from where you park and will take you to the highest spot in the Smokies. There’s an observation tower at the top. You can also hike part of the Appalachian Trail (71 miles of which run through Smoky Mountain National park) — you could make this a couple of day excursion or just a short section.
After you’re through the park, you’ll head to Dollywood, Dolly Parton’s theme park is (and always will be) one of my favorite places on earth. It doesn’t feel quite like just a theme park, from bluegrass and country shows to the artisans doing crafts like glass blowing to the eagle sanctuary, to a recreation of Dolly’s childhood home, to the best ride (in which the premise is that you’re in a fire in the mines and then probably die when the tunnel collapses. I love a childhood ride that allows you to experience your own death), it’s a beautiful, unique park that feels very much in service to its Smoky mountain roots.
Make sure not to miss: Gatlinburg and Pigeon Forge, the towns you’ll pass through to get to Dollywood, are set in a beautiful location and are uniquely quirky. They can err on the side of touristy, like very touristy, but at some point a place is so touristy that the weirdness becomes delightful. Embrace it, go to one of the very weird dinner shows, stroll past an upside down building, and ride on the Gatlinburg Sky Lift.
Song to play: Endless Highway, Alison Krauss
-AS
Download the playlist for your own roadtrip!
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