Driving cross-country is an ambitious journey that always sounded a bit more romantic to me in theory than in practice.
But when my partner convinced me to expand my horizons a few years ago, we started planning with the Ralph Waldo Emerson adage “it’s not the destination, it’s the journey,” as our guiding principle.
We drove a total of 6,036 miles cross-country from New York to my hometown of San Diego and back — and I figured we might as well see as many cool and quirky things along the way as possible.
Here are the places we stopped that I would go to again and the spots I’d skip next time.
After leaving New York, our first stop was in Pittsburgh, where we ate pizza and visited The Andy Warhol Museum.
I married a Pittsburgher and have visited the Steel City many times.
So, first, we made a requisite stop at the Strip District to try Pizzeria Davide, then headed over to the Andy Warhol Museum.
After touring the exhibits, I thought it was an absolute must-visit for anyone in Pittsburgh to witness more than seven stories of some of Warhol’s (a Pittsburgh native) most seminal works of art.
The museum was also well-placed to follow with a stroll to The Point downtown where the Monongahela and Allegheny Rivers merge into the Ohio River.
We left Pittsburgh en route to Cincinnati, stopping at Buckeye Lake State Park to stretch and grab lunch.
A halfway point between Pittsburgh and Cincinnati, Buckeye Lake State Park is touted as Ohio’s oldest state park.
It’s also home to a local winery, brewery, and beer pier, which sounded intriguing and looked to be an ideal spot to stop and refuel.
We didn’t find a wide range of food options in the area and weren’t particularly impressed, although we did enjoy getting out here and stretching our legs.
Next time, we’d try stopping at a different park.
From Cincinnati, we drove to Nashville, where we had drinks at a Dolly Parton-themed restaurant.
The road to Nashville was peppered with many cool pit stops, but due to bad weather, we bypassed places we’d been looking forward to, like Louisville and Bowling Green, Kentucky.
Instead, we went straight for Nashville, arriving hungry and ready for a drink at White Limozeen, a Dolly Parton-themed rooftop restaurant located just off the Vanderbilt University campus.
We sat alfresco overlooking a giant Dolly Parton bust and didn’t miss a chance to try the signature champagne Jell-O shots, which come topped with sprinkles. We also had Nashville hot chicken sandwiches.
Along with the pink décor and convivial rooftop vibes, the stop was a pleasant and completely unexpected surprise.
It was definitely worth a visit, but next time, I’d come here just for drinks and save dinner for The Pharmacy Burger Parlor and Beer Garden, where we ate the best burger of our trip.
Next, we stopped at one of my favorite barbecue joints in Memphis before driving through Ozark National Forest to a memorable hotel.
After a quick stop at one of my all-time favorite barbecue joints, The Rendezvous in Memphis, we headed through the wilds of Arkansas’ Ozark National Forest — one of the greenest and most scenic stretches of our drive.
Along the way, we paid a last-minute visit to Fayetteville, a charming college town tucked away in the northwest pocket of the state.
There, we enjoyed a casual dinner on the patio of a former post office called Cheers at the OPO (for Old Post Office) and decided to tuck in for the night next door at a quirky local hotel, the Graduate.
The Fayetteville-themed lobby, complete with camouflage carpets and Arkansas ephemera displayed all over the walls, was a fun touch. We loved the hometown pride that this place had to offer.
We continued along Route 66 and spotted an unusual roadside attraction on the way to Oklahoma City.
The ride through the plains of Oklahoma provided a stark contrast to the lush and wild landscapes in Arkansas.
We made our way through Tulsa, home to architectural marvels such as The Philbrook Museum of Art and one of the largest collections of Art Deco architecture in the country.
However, our stop at The Blue Whale of Catoosa off of Route 66 was a tiny bit underwhelming.
We learned that this giant 80-foot sperm whale was built as a diving platform and slide for kids in the early ’70s and has been basically marooned ever since.
Though I can see the appeal if you have young kids in tow — and we did see several families with children who could not have been more delighted by this unique sculpture — it wasn’t a must-stop spot for us.
Just off Interstate 40, Cadillac Ranch outside Amarillo, Texas, was an Instagram-worthy surprise.
It was windy and dusty the day we visited Cadillac Ranch, a free public art display that’s well worth a quick visit to walk around and snap some photos.
It’s comprised of a colorful collection of upended Cadillacs covered in paint. You can bring your own spray paint or buy some from one of the local vendors just outside the entry point to tag the cars if you’re so inclined.
Though we didn’t partake, I’m glad we stopped to check it out for the photos alone. For us, a single visit was sufficient. We didn’t feel the need to return on our way back to New York.
When we drove through Texas on our return, we stopped in Odessa to see a replica of Stonehenge.
Set on the University of Texas at the Permian Basin Stonehenge campus, the Stonehenge replica is made up of 19-foot-tall slabs of limestone and was assembled in the early 2000s.
It’s designed to serve as a teachable moment for students and visitors here, but because I’ve visited the original Stonehenge, a UNESCO World Heritage Site that dates back some 5,000 years, when I was traveling across the UK, I would skip this next time.
Nothing can truly compare to the original.
We skipped Dallas in favor of Fort Worth, Texas, where we saw dozens of longhorn cattle walking through town.
The daily cattle drive in Fort Worth happens twice a day and was one of the coolest things we witnessed on our trip.
It also made us feel like we were front and center in an old Texas Western, as Fort Worth is full of honky-tonk restaurants and old-timey boutiques, plus Stockyard Station, which is lined with fun shops.
There’s also the Cowtown Coliseum, which is home to the country’s only year-round rodeo. Although we didn’t get to visit it on this trip, we would definitely check it out in the future.
After Texas, we continued west to Santa Fe, New Mexico, where we stopped at a thermal spa.
Tucked in the foothills just outside Santa Fe, New Mexico, Ojo Santa Fe Spa is known as one of the country’s oldest natural health spas, dating back to 1868.
Between its spa and spring-fed thermal pools, it was a much-needed stop for a little rest and relaxation.
The spa was closed during our visit, but we still enjoyed soaking in the geothermal mineral water, which is said to have healing properties. After spending a full day here, I’m a believer in the healing powers of that water and would definitely stop here again.
In Santa Fe, we also paid homage to the Georgia O’Keeffe Museum before checking out the galleries and boutiques found along Canyon Road, both of which were worthwhile stops.
Along Route 66, Petrified Forest National Park in Arizona was a last-minute stop that I wouldn’t hesitate to visit again.
Driving into the Petrified Forest National Park felt like driving through one of Georgia O’Keeffe’s abstract paintings.
The Mars-like landscapes, featuring red and beige sandstone rock formations, were utterly surreal and one of the best unplanned stops we made along the way.
Said to be more than 200 million years old, the park offers numerous places to stop and explore throughout its grounds.
We decided on The Painted Desert Inn, an adobe building dating back to the 1930s, and Newspaper Rock, which features the park’s largest concentration of petroglyphs carved into boulders by the ancestral Puebloan population that dates back thousands of years.
The carvings at Newspaper Rock can best be seen through binoculars or a telephoto lens, the latter of which I was glad to have on hand.
It’s definitely worth a visit to witness this awe-inspiring landscape.
On the home stretch, we couldn’t leave Arizona without seeing the Pillar at Cathedral Rock in Sedona up close.
There’s no shortage of ways to see and experience Sedona’s vast landscapes, but one place we couldn’t leave without seeing was the view of Sedona from the summit of Cathedral Rock.
I will admit, we were not well-prepared for the intensity of this 1.2-mile out-and-back hike. It’s labeled as “moderate-to difficult” by AllTrails.com and “popular for hikers of all ages,” but the nearly vertical climb and slippery rocks were challenging for a lot of people on the trail that day, ourselves included.
However, the views from the top were out of this world. I would definitely stop here again, although I would plan accordingly and bring more water and better shoes next time.
On our way out of Sedona, we stopped at Yavapai Apache Fry Bread & Jewelry.
Yavapai Apache Fry Bread & Jewelry is just off Route 17 outside Sedona. Its selection of Native American jewelry, crafts, crystals, and sweet and savory fry bread made this a great place for a quick break.
Located outdoors under a tent, there were tons of unique souvenirs, including a dream catcher that I now have hanging above my bed.
The made-to-order fry bread topped with powdered sugar that we got was delicious, and an added bonus.
The final stop of our road trip was in Temecula, California, to try chocolate wine.
The Temecula Valley is a burgeoning wine region in Southern California.
Although it’s often overlooked in favor of the wineries to the north in Napa and Paso Robles, its Italian and French grape varietals and tasting experiences are definitely worth checking out.
We stopped by Thornton Winery for a very special case of wine and a quick tasting.
Considered “the original champagne house,” Thornton is known for its old-world champenoise method of winemaking, along with its coffee and chocolate wine flights.
After driving more than 3,000 miles across the country, my horizons had been broadened, and a case of wine called Milk Chocolate Kiss was the very sweet cherry on top.
This story was originally published on January 22, 2022, and most recently updated on December 1, 2025.
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