Say's Crazy Road Trip Stories

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By Madeline Klein on April 3, 2020.

Not every road trip goes exactly as planned, so read about some of our own that didn’t!

Years ago, before the invention of driving apps, my husband and I decided to travel to a big city here in the Midwest. We drove into the night attempting to find the famous basketball stadium and quickly got lost. After taking a few wrong turns, we entered an area of town that was a bit dicey. We came to a four-way stop and found a car on its roof in the middle of the intersection! No one was inside, so I told my husband, “Floor it! We better not stop for any reason!” We missed the game that night, but I was glad to be alive!

  • Sara S.

When I was young, my grandpa took me on a road trip to Virginia Beach to visit my mom and stepdad. Grandpa was an outstanding storyteller, and he had an endless supply of jokes. He was also notoriously frugal seeing as he grew up in the Great Depression. This turned out to be the ultimate driving combination for my ten-year-old self. We spent the day swapping antics and only stopped for dinner at local eateries. I swear, my grandpa had built-in radar for awesome diners. We also took time to stop at some famous sights along the way. My favorite was Churchill Downs. The places we stayed are likely long-gone, but these are memories I will treasure forever.

  • Marc D.

The summer of my sophomore year in high school, my family road tripped to Yellowstone. We closely resembled the Griswolds in our stuffed car. Dad over packed, and the back seat was almost too full for my brother and me to fit! Somewhere around Rapid City, IA, we began losing our sanity. At first, it was a misplaced favorite pen, or cassette tape (yes, cassette tape – they had those in the 80’s), but it gradually progressed into more serious items like our gas cap and my mom’s diamond earring that fell somewhere in Deadwood while panning for gold. On our way home, we passed through the Badlands National Park.  We were so mesmerized by the majestic view that we got out of the car and began snapping photos of the mountains and wildlife. When we returned, we were horrified to find we left the windows open. Fortunately, no cassettes were taken (and the other contents of our vehicle were intact)! The drive was long, hot, tiring, and we had very little personal space, but it made for a memorable and hilarious family vacation.

  • Jennifer C.

Crazy road trip huh?

My craziest road trip was about 4 years ago. After graduating college, a friend and I took two weeks determined to explore the Southwest corner of the U.S. We made our first stop in Santa Fe where we intended to camp for the night but were greeted with a thunderstorm to remember. The first discovery of the trip was the gaping hole in the top of my new tent. The next morning, we headed to Albuquerque, NM, to rest and spend some time with my extended family. The following day, with a new tent in tow, we headed for the Gila Wilderness. Here we spent a few days in the desert on a backpacking trip. We even found a hot spring before heading to the U.S./Mexico border! The next few days we traveled through Arizona, Utah, and Colorado. Unfortunately, our final night was about as eventful as our first when my friend’s new bike was stolen. Thank goodness we didn’t need that bike to get home!

  • Alex N.

As recent high school graduates, my friends and I decided to road trip to Destin, FL. We borrowed an old-school van and planned to stay in a trailer a few miles from the beach. We didn’t have much money, but we were determined to celebrate our newly achieved freedom! A few hours into, the trip the AC in our 15-passenger beast stopped working. I have never been so grateful for car curtains in my life! Fifteen hours later we made to the beach. Our time in Florida was a blast and the memories made on that trip will stay with us forever, but the real lesson learned on this vacation was to get your vehicle checked before taking a lengthy road trip!

  • Erin T.

Let me start by saying, this was not supposed to be a road trip. I flew to visit my brother in Austin, TX and arrived without any issues. On the way back, things got a bit tricky! I flew to Dallas only to find my connecting flight was canceled! It was 2 a.m. on Monday morning, and I was expected to be at work by 8! I couldn’t make it back to Austin to crash with my brother, and the next flight home wasn’t until Tuesday night! This predicament meant I would miss two full days of work, and I was not prepared for that. After a few hours, I met a couple people in the airport from a town neighboring mine. We all decided to pitch in and rent a car. We drove the 12 hours back to Columbia, MO and made it back faster than any rescheduled flight option. It was an interesting drive that allowed me to make some new friends!

  • Paige W.

My buddy and I transferred to the same college in 2010, so we decided to make a road trip out the long drive. This college was in northern California, about 6 hours from our home. Around that time, Taco Bell brought back the Cherry Limeade Sparkler. After the first drink, we were ADDICTED. We stopped at every Taco Bell we saw along the way to get another deliciously fruity drink. This 6-hour trip ended up taking 10 full hours because we could not curb our addiction. I hope Taco Bell brings those drinks back this summer!

  • Steven C.

Madeline Klein is Say's Digital Content Producer. She graduated from the University of Missouri with a Bachelor of Journalism, emphasis in Strategic Communication. Her experience is in writing and digitial media. Madeline loves using her creativity to write and design new and exciting pieces of work for Say!