From Chicago to LA! How we crossed America on the ultimate road trip


Road trips might not be for everybody. But they are definitely for me.

My desire to be on the open road probably began when I was about 17 and was introduced to the Beat poets. Like every angst ridden teen I read Kerouac’s On The Road and dreamed of Big Sur.

As an adult I was lucky enough to do two road trips up and down the Pacific Coast Highway, taking in every spot between San Francisco and San Diego.

My road trip obsession grew.

I even undertook much smaller UK based trips with an old school friend in her VW camper van, trying to get that feeling of freedom that for me, only comes with being on the move.

So when my boyfriend’s niece asked if I would drive with her from Chicago to Los Angeles where she goes to college, I could not have been more excited.

Flights were booked, a bag was packed and we set off on an adventure I never thought I would have. My own American dream and a truly epic American road trip. 

Getting on the road

My welcome party on arrival in Chicago

Chicago, Illinois to Jackson, Minnesota

Esme met me at the airport carrying a homemade ‘Welcome to the USA’ sign, and we got straight on the road. It may have been our first day driving together but we had a lot of ground to cover straight away, so after a quick pit stop to pick up iced coffees and donuts (classic road trip sustenance) we were on our way in faithful Pat, the Jeep Patriot. She had already crossed the country more than once so we just hoped she could keep going all the way to the West Coast again. Spoiler alert: She didn’t let us down.

Most road trippers who want to go from East to West take the iconic Route 66. It provides the straightest line, after all, (and there’s a song) but we had other plans. As we wanted to end our week by doing the Pacific Coast Highway and Big Sur, we headed north, first driving through Wisconsin.

The view from the windows was extremely pretty with plenty of white picket fences and iconic red barns. When we were close to the Minnesota state line, we stopped off to buy some Amish candy (delicious) and I took my first turn behind the wheel (scary).

The Old Railroad Inn provided our first night's accommodation and a very comfortable bed

The Old Railroad Inn provided our first night’s accommodation and a very comfortable bed

The roads aren’t as daunting as you might imagine but I was definitely a little cautious. We crossed the enormous Mississippi, driving through miles and miles of road works and finally arrived at our first overnight stop; a truly tiny town called Jackson in Minnesota.

We pulled up at our BnB which was very cute but extremely chintzy with frills, doilies, flowers and pot pourri in every available spot. We were starving so went straight to the centre of town which really didn’t consist of very much, opting to eat at the sports bar, one of only two restaurants open on a Saturday night.

We couldn’t quite bring ourselves to eat the ‘salad’, so stuck to the mac ‘n’ cheese and fries. One major plus point, however, was the $3.50 margaritas. To say we looked and sounded like a couple of outsiders is an understatement. 

It was the perfect first night. 

Epic Day 2

Sioux Falls, South Dakota

Sioux Falls, South Dakota

Jackson, Minnesota to Buffalo, Wyoming

Today we drove almost 640 miles, crossed a time zone and took in three states. And wow, was it epic.

We left our little Jackson BnB early (thank you jet lag) and got to the city of Sioux Falls in South Dakota by about 9am. This outpost has had a bit of gentrification thanks to an influx of professionals arriving when Citi Bank moved its headquarters here.

So there’s a cute downtown artsy district and plenty of places to pick up a delicious coffee which we did at a hipster joint called Source. But first we took in the falls that give Sioux Falls its name and they’re impressive, especially considering they’re essentially in the middle of a municipal park.

After breakfast (served by a very nice girl from London – what are the chances?) we hit the road again and drove the nearly 300 miles to the Badlands.

Anywhere called the Badlands has got to be incredible and it didn’t disappoint

Anywhere called the Badlands has got to be incredible and it didn’t disappoint

The iconic Badlands

Crossing the state line into Wyoming

The iconic Badlands and the Wyoming state line

Anywhere called the Badlands has got to be incredible and it didn’t disappoint, although getting there was a little hairy when we both came down with what we decided to call delirium; forming sentences was hard, we felt like we were in a dream, things went a bit squishy… Only later did we realise we were very dehydrated, but thankfully we got there without any actual mishaps.

Badlands is crazy. It was hot with no respite or shade. The pink and yellow striped rock formations go on and on for what seems like forever. It was thrilling to be there but just difficult to take it all in.

Our epic day wasn’t even nearly over. An hour and half and we were at Mount Rushmore. And while the carved rock faces are as you imagine and definitely very cool, it was the beauty of the Black Hills National Forest that really took our breath away.

As we came out the other side we crossed into Wyoming, where the sky was big. We were treated to an intense storm complete with torrential rain, driving winds and lightning strikes lighting up the road ahead of us. We hadn’t actually reserved a place to stay that night so all through the storm we tried to find somewhere we could lay our heads.

We finally found a remote lodge on the other side of Buffalo that could fit us in. So after a quick bite to eat, we crashed out in our cabin long after the sun had gone down and with no idea what the world outside our window looked like. 

Beautiful Day 3

Our cabin in Bighorn National Forest was a little remote...

Our cabin in Bighorn National Forest was a little remote…

Bighorn National Forest, to Jackson Hole, Wyoming

Our lodge was in the Bighorn National Forest and from the second we set off in the morning, the landscape was unbelievably beautiful.

Winding roads with steep drops took us through towns with names like Tensleep (pop. 260), and after an hour or so we stopped in Worland for a classic diner breakfast at a locals’ spot called Maggie’s. The food was delicious but the fact we didn’t want any meat with our eggs, avocado and spinach was mystifying to the waitress and the chef, who asked us more than once ‘no meat?’ 

No, no meat.

Today was all about getting to Yellowstone and the drive was awesome. The views change almost constantly and very abruptly. One second it’s red, then everything is yellow, then pale green. Next you’re in a forest, then passing ranches and whatever it looks like, it goes all the way to the horizon in every direction. America is vast!

The vast Yellowstone Lake

The vast Yellowstone Lake

Tears may have been shed at the mind blowing Lower Falls

Tears may have been shed at the mind blowing Lower Falls

The bison of Yellowstone and their traffic jam

The bison of Yellowstone and their traffic jam

We weren’t sure what to expect from Yellowstone but whatever image had been in my mind was just wrong. It’s huge for a start and would require a full week to really feel like you had even begun to grasp all it entails. There’s an enormous lake up there. Who knew? There are plains and valleys, hills and cliffs, canyons and geysers and one of the most amazing waterfalls I’ve ever seen. The raw beauty and scale was overwhelming and I may have even cried… And while we got stuck in a huge traffic jam thanks to some (adorable) bison who refused to get out of the road, we still left feeling we’d seen a lot.

The journey out the other side of Yellowstone into the Grand Teton National Park eased the sadness of leaving Yellowstone. With amazing landscapes all around, it’s impossible not to keep looking forward. With a prairie on one side and a lake and mountains on the other, we made our way into Jackson Hole, a renowned high end ski resort in the winter months.

Anvil Hotel, Jackson Hole: Our first taste of luxury after two nights on the road

Anvil Hotel, Jackson Hole: Our first taste of luxury after two nights on the road

The Anvil aesthetic is an understated and timeless utility-chic. Think iron frame beds, custom brass fittings and cosy Woolrich blankets

The Anvil aesthetic is an understated and timeless utility-chic. Think iron frame beds, custom brass fittings and cosy Woolrich blankets

We had booked a one night stay at the Anvil Hotel, a converted motel which is now a seriously stylish boutique hotel. We figured we would, by now, deserve a night of well earned luxury. But this was a cool, vintage-inspired take on luxury and it suited us down to the ground.

The aesthetic is an understated and timeless utility-chic. Think iron frame beds, custom brass fittings, Woolrich blankets, painted wood panelling, clean lines and all with a view out to the slopes of the Tetons. It cleverly combines a modern-rustic look with a feeling that it has been there forever. Cosy, welcoming, with all the comfort you’d hope for, but with a little edge too.

Dinner at Glorietta was a joy, especially after a diet of road trip food

Dinner at Glorietta was a joy, especially after a diet of road trip food

Dinner at Glorietta was a joy, especially after a diet of road trip food

We can highly recommend the Smoke Show and the Cat's Pajamas

We can highly recommend the Smoke Show and the Cat’s Pajamas

We ate at the hotel’s restaurant, Glorietta which was clearly the ONLY place to be seen in Jackson Hole and were looked after by the very charismatic manager Chuck and our knowledgeable waiter Ray. The place was packed and the atmosphere vibrant, with a mixed clientele of hip 20-somethings and wealthy older couples who were all clearly here for the vibe as well as the incredible food. You could almost be in Brooklyn or London’s Shoreditch.

After a couple of days without fresh ingredients and a lot of road trip fare, our dinner at Glorietta was not only completely delicious but a welcome change too. We both had perfectly cooked salmon and corn and shared a plate of the vegan pasta, while sipping on cocktails. 

It couldn’t have been more different from our first dinner on the road, back in the sports bar in the other Jackson…

One last drink at the Billion Dollar Cowboy Bar, where the bar stools are made from saddles and where actual cowboys hang out, and it was time for bed back at Anvil, falling asleep as soon as our heads hit the ridiculously comfy pillows.

California, here we come

Our cabin at Lake Tahoe

Our cabin at Lake Tahoe

Jackson Hole, Wyoming to Lake Tahoe, California

From Jackson Hole we left Wyoming and drove through Idaho and northern Nevada to eventually cross the state line into California. It was hard to believe that after only four days we were now approaching the west coast already.

Kings Beach, Lake Tahoe

Tacos on the beach? But of course...

Who wouldn’t want to live at Lake Tahoe?

Today we decided we’d like to live at Lake Tahoe. Although we’d already decided we’d like to live in Jackson Hole so we’re clearly very easily swayed.

But it was so special. We arrived at our incredibly sweet wooden cabin which was pretty much on the shore in North Tahoe in time for lunch and after changing into swimsuits and running straight into the lake, we grabbed some tacos which we ate on the beach.

It was warm, the lake was sparkling in the sun and we felt this could be heaven.

The end of the trail to Hidden Beach

Picking up tacos

We finally stopped moving at Lake Tahoe 

We spent the afternoon at a hidden beach on the eastern side of the lake which can only be reached via a woodland trail. It was deserted and peaceful and after being on the move constantly, it felt good to just lie in the sun.

The best day ever  

Swimming in the Merced River under the shadow of Half Dome

Swimming in the Merced River under the shadow of Half Dome

Lake Tahoe to Groveland, California 

Our next day was one of those days I’ll remember forever. It’ll be the day I bore my family and friends about at every opportunity from here on out. 

Tahoe was dreamy but we had to keep moving, so rose early and took ourselves and a flask of tea, down to the lake for a chilly morning dip. After picking up sandwiches from the local deli we set off in Pat with a day at Yosemite in sight.

The drive was beautiful from the outset, with the roads winding around the mountains and after only a couple of hours we arrived at Lake Mono on the edge of Yosemite. From there we took the Tioga Pass, which is closed for much of the year as it’s deemed too treacherous in bad weather, and drove into the heart of the park where we were surrounded by sheer cliff faces and snowy peaks.

The beautiful Lake Tenaya where we stopped for a swim

The beautiful Lake Tenaya where we stopped for a swim

Lake Tenaya

A view of Half Dome

Lake Tenaya and a view of Half Dome before we drove down into the Valley

As we drove past Lake Tenaya, the water looked so clear and was sparkling so beautifully in the sun, we pulled over, changed into our swimsuits and dived in.

It was one of those occasions when you can’t quite believe you’re there. You’re swimming in a lake in Yosemite. It wasn’t planned, it just happened. And it was these moments of freedom and spontaneity that elevated the whole experience to something more than a holiday.

It provided an escape from being a grown up and from all the worries and anxieties of everyday life. I felt a weight lift as we dried off in the sun, enjoying our Tahoe picnic. 

And the day just continued in the same way. More ‘drop of a hat’ swimming, this time in the Merced River down in Yosemite’s Valley and more disbelief as we took in the grandeur of El Capitan and Half Dome. 

The Chick-Inn, Groveland, California

Our outdoor eco-loo and shower

The Chick-Inn, Groveland, California and our outdoor eco-loo and shower

Leaving the beauty of Yosemite was a wrench but we were excited to see where we were staying that night; a vintage caravan called The Chick-Inn just outside the old gold mining town of Groveland. 

It was every bit as cute and quirky as we’d hoped and we were even treated to the joys of an outdoor eco-loo and shower with views over the hills.

What a way to end the most perfect day.  

Reaching the Pacific 

Did someone say 'living my best life?'

Did someone say ‘living my best life?’

Groveland to Carmel, California

Call me a geek but I love the Monterey Bay Aquarium.

And that was our destination after leaving The Chick-Inn. At breakneck speed I might add as I was so desperate to get to the sea otter feeding. Esme had never seen me drive so fast!

We didn’t make it in time, but we did spend a couple of very happy hours watching those adorable creatures playing and sleeping, as well as gawping at the all the jellyfish, deep sea critters and Cephalopods. 

The beach at Carmel-by-the-Sea

A fairy tale building in lovely Carmel

The beach at Carmel-by-the-Sea and a fairy tale building in town

We were nearing the end of our road trip by this point so every second felt precious. We took the 17 Mile Drive along the coast down from Monterey to the extremely pretty and ultra luxe village of Carmel-by-the-Sea. This is the town where Clint Eastwood was mayor after all.

It really is the most lovely place and after a wander through its charming streets and checking out its fairy tale buildings, we thoroughly enjoyed the complimentary wine hour at our gorgeous hotel, The Hotel Carmel.

We sipped our Californian white while we read the local paper, The Carmel Pine Cone (how cute can one place get?) and I tried to forget we were on the last leg of our journey. 

The end of the road 

Bixby Creek Bridge as seen on Big Little Lies...

Bixby Creek Bridge as seen on Big Little Lies…

Carmel to Los Angeles, California

Leaving Carmel and arriving in Los Angeles to stay with friends for our last night was bittersweet.

As excited as I was to drive the Pacific Coast Highway, I couldn’t help but see it as the end of what had been the most carefree and fun week of my life.

I spent most of the drive trying to hold back tears, feeling envy towards the locals whose time in this beautiful place was clearly a day trip, whereas for me it was the first stage of my journey back to real life.

The Big Sur Bakery

Elephant Seals at San Simeon

Final road trip baked goods were bought at the Big Sur Bakery before chatting with the noisy Elephant Seals at San Simeon.

But I dragged myself out of my self-obsession to enjoy the last few hours and while the infamous northern California fog made its presence felt, Big Sur and the coastline were as wonderful as I remembered.

We stopped for insanely delicious pastries inland at the Big Sur Bakery before breaking out of the fog as we reached San Simeon, where we had to pull over to say hello to the very noisy Elephant Seals.

On a deadline to get to LA, we left Route 1 and got on the interstate, arriving with our friends in Hollywood in the early evening. They welcomed us with homemade margaritas which went a little way to take the edge off the fact this was the last night.

Esme drove off to college in the morning and I flew back to London and I’ve been dreaming of being no the road ever since.

Thank goodness our next adventure is already booked!