Road Tripping Across America: My Northern and Southern Cross-Country Routes

Road trip scenery

There is nothing like a cross-country road trip to capture the spirit of the United States. While cliché, there is truth to what they say – the freedom of nothing but you, your car, an open road, and infinite possibilities ahead of you feels inherently American. So which way do we go?

The first time, I chose to drive the northern route from San Diego, CA to Pittsburgh, PA. The road-trip was a cathartic experience, as I left my life in San Diego in order to make the transition to Pittsburgh for a graduate program at Carnegie Mellon. With each new day on the road, I slowly but surely rediscovered that spirit inside of me that had been dulled by years of routine and disconnectedness.  The challenge of the logistics on the road and the surprises that seemed to come with every turn was food for the soul.  My dad always gently reminded me that change and new environments bring new ideas. This trip drove that wisdom home.

Cross-country road trip San Diego to Pittsburgh

The second time I crossed the U.S. by car, I was returning to San Diego after finishing my studies in Pittsburgh.  My road trip mate was a great new friend I had studied with at Carnegie Mellon.  Both of us were riding high from the excitement of our school experience, and the holidays, as we were making our drive in the last few days leading up to Christmas.

Since I drove the northern route from San Diego to Pittsburgh, I decided to drive the southern route from Pittsburgh back to San Diego.  The timing worked out well, as the southern route was a better choice for driving during the winter months, while the northern route had been a good choice for our summer trip.

You can follow the links below to learn more about our route and see my trip highlights for insights.

San Diego to Pittsburgh Itinerary

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San Diego to Pittsburgh Road Trip Itinerary

Day 1: Las Vegas, NV
Day 2: Zion National Park, UT
Day 3: Best Friends Animal Sanctuary – Kanab, UT
Day 4: Denver and Boulder, CO
Day 5: Rocky National Park – Estes Park, CO
Day 6: Mount Rushmore – Keystone, SD
Day 7: Iowa City, IA
Day 8: Chicago, IL
Day 9: Chicago, IL
Day 10: Pittsburgh, PA

Favorite Day of the Trip: Our day in Denver and Boulder, CO. Both cities were beautiful and dynamic, full of great things to see and explore, great food, great beer, and a nice vibe. I would like to spend more time in both places. Each day was incredibly special, actually. And our time at Best Friends Animal Sanctuary is also a day I won’t soon forget.

Most Random Experience: On the way out of South Dakota we ran into the Sturgis Festival. I don’t think I will ever see so many motorcycles in one place again. The rainstorm while we were staying at the Stanley Hotel in Estes Park, CO, which is the inspiration for The Shining, was also quite memorable.

Favorite State: Utah. Unbelievably beautiful.

Best Meal: Chicago deep dish pizza.

Biggest Surprise: Iowa! Iowa was a really dynamic state, full of universities and cool people. My friends live in Iowa City where we visited them. The city architecture was interesting, the food was great, and we loved our stroll around town with them.

Driving Insights: In general, the driving was not too demanding. It was only our nighttime driving that became a bit more challenging at times. Driving through the wilderness around Zion National Park to get to the small town of Kanab, Utah was tougher in the dark, with very windy roads and no streetlights. Approaching Denver at night was also harder, with a tremendous elevation gain. Rocky Mountain National Park during the day was easy and gorgeous, though, despite the windy roads.

Pittsburgh to San Diego Itinerary

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Pittsburgh to San Diego Road Trip Itinerary

Day 1: Charlotte, NC
Day 2: Jacksonville, FL
Day 3: New Orleans, LA
Day 4: New Orleans, LA
Day 5: Austin, TX
Day 6: Carlsbad, NM
Day 7: Phoenix, AZ (by way of Tucson, AZ)
Day 8: El Centro, CA
Day 9: San Diego, CA

Favorite Day of the Trip: We spent a full day exploring New Orleans, and that was definitely the highlight of the trip.

Most Random Experience: My friend was celebrating a birthday the night we arrived in New Orleans. There is a Four Seasons near the hotel where we were staying, and we decided to check out the Four Seasons because they are always so beautiful. On the elevator, we made friends with some travelers who ended up secretly arranging drinks and dessert for us to celebrate my friend’s birthday. It was an unexpected bit of kindness that made our day.

Favorite State: Texas. There were so many cute towns and funky things to check out on the side of the road.

Best Meal: Every meal we ate in New Orleans. We also loved checking out the food trucks in Austin. And I’ll never forget the fried green tomatoes in Charlotte.

Biggest Surprise: I had been really excited to finally get to visit Austin, but I must admit, I was surprised that Austin wasn’t a very walkable city. I had always assumed that since it was a college town, it would be a place where we could spend more time out of the car, exploring a bit on foot. But you really need a car to get around most neighborhoods in Austin. I still enjoyed it, though, and hope to go back soon and get to know it better.

Driving Insights: The nighttime driving was again the only time I experienced challenges. Approaching New Orleans was a bit tricky going over all of the bridges at night. I’m sure once you get used to it, it isn’t a problem, but for our first time, we were caught off-guard. Other than that the drive was easy. It does get hot and that sun is quite bright even in the winter, so make sure to carry extra water with you.


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