Part 1 - Start of the Cannonball Run

July 17, 2023

Prior to starting our Cannonball Run, I knew that the trip would be a massive undertaking. However, I definitely still underestimated how massive. As previously stated, the trip would entail nearly 4,500 miles of driving over a 10 day period.

Day 0 (Thursday, July 13) - Flight from Atlanta to Newark

Two words could be used to describe how I felt on the morning that we flew out: excited and anxious. My excitement came from the past year of planning this trip, while my anxiety was primarily around whether or not I had bitten off more than I could chew and what our rental car would actually be.

While I was wrapping up my half-day of work on Thursday, my smile was ear-to-ear and I definitely looked like a kid in a candy store. Those were the longest 4 hours of work I have ever had. When noon FINALLY rolled around, I went ahead and booked my Uber to the airport. You can see the excitement on my face as I was walking outside with all of my luggage!

In case you're wondering why I am wearing a cowboy hat it's because I didn't want to cram it in my bag and potentially damage it (I'm generally pretty bad about ruining nice things). I have to have my hat to wear while I'm out west, especially in Jackson, WY!

The Uber took a bit longer to arrive at the airport than normal (Hartsfield Jackson airport traffic was terrible), but I made it to the gate for boarding. When I finally met up with Jake, our excitement was pretty hard to hide...

Upon arrival at Newark Airport, we quickly picked up our checked bags and anxiously went to the Avis lot to see what we would be in. I glanced down at my phone while on the way to see that our rental Toyota Sienna (minivan) was already prepped and ready to go...

The good news is that we were already planning to swap the minivan for something else, we just didn't know what else might be available. Once we got to the Avis lot, we walked through the lobby and straight out to the lot to see was available. We had a couple of options, but the one that we inevitably selected was a 2023 Ford Mustang Eco-Boost. While we were hoping for something that was potentially a bit more powerful, we were both happy to have a sporty American car to go on an American cross-country run; it felt quite fitting.

We left the airport and went to Jake's aunt and uncle's home for dinner in New Jersey, where we also met with Jake's Grandmother. After dinner, Jake's Grandmother decided that she would join us in going to Manhattan, specifically the Red Ball Garage to take our Cannonball Run picture. Before either Jake or myself could even get in the car, Jake's Grandmother was already hopping in the backseat (please note that Jake was planning to ride in the back seat) and seemed as excited as we were for the upcoming adventure. From there, I hopped in the driver's seat and headed straight for the city.

I had always been nervous to drive in Manhattan, but once we were there it really was not as bad as I expected. We made it to the Red Ball Garage around 10:30 PM. While we weren't doing a competitive, timed run it felt ceremonious just to be there. We could finally see the fruits of our planning efforts (even Risa, my wife, would be proud of my planning abilities on this trip) which felt great!

After we truly "started" the trip in New York City, we drove back to New Jersey where we stayed with Jake's Grandmother for the night. I don't think Jake or I slept well that night because the excitement and anxiety were the only things on our mind...

Day 1 (Friday, July 14) - New Jersey to Chicago

Time: 8 Hours

Miles: 780

To begin Day 1, we woke up at 6:30AM, packed the car, and had breakfast with Jake's Grandmother and a close family friend. Before departing, we were given a traditional grandmother gift basket with bagels, orange juice, Gatorade, and various other snacks/drinks. It was a great way to start the first of 2 big days. Here was a picture I took right before we left:

The drive between New Jersey and Chicago was honestly pretty easy with no callouts or issues. The day went by pretty quickly and we crossed off our first few states:

1. New York
2. New Jersey
3. Pennsylvania
4. Ohio
5. Indiana
6. Illinois

We also had a number of gas fill-ups, here were a couple of pics from them:

Somewhere in Pennsylvania for our first gas fill-up

Somewhere in Ohio. Every service station was the exact same across the state.

We arrived in Chicago around 6:00 PM CST for our stay at the Courtyard Marriott. We showered, changed and went for a walk in the city. We walked from the hotel to Millennium Park to enjoy the view after the crazy day.

We then realized how hungry we were. We went on Google Maps and tried to find a restaurant that sounded appealing and something local. We ended up finding the most local dive possible: Billy Goat Tavern, which is literally underneath the city of Chicago. Both the food and atmosphere were great.

As we happily ate our burgers, the anxiety started to grow about the drive for the next day (some foreshadowing there). We quickly made a rule not to talk about it and to just enjoy the night in Chicago.

After finishing dinner at Billy Goat Tavern, we went over to the Riverwalk to grab a beer, but ran into a problem as we sat down and noticed there was a severe thunderstorm rolling in (meaning it probably wasn't a great idea to be outside). I looked around and found a local brewery where we went instead called Crushed By Giants Brewing Company, which was a perfect sedative to get some early sleep before the upcoming sprint of the next day.

One thing that we didn't think through there was a severe thunderstorm and while we were not in it at the Riverwalk, we still had to walk from the brewery... Needless to say, others will probably find this video entertaining...

Day 2 (Friday, July 15) - Chicago to Billings

Time: 19+ hours

Miles: 1,300

Day 2 was the CRAZIEST day of this entire trip. To this point in my life, the longest trip I had ever taken was about 12 or 13 hours from Albuquerque to Los Angeles. I had been nervous about this drive for literally months, but it was finally time to go for it.

We woke up at 3:45AM to start the drive. About 2 hours later, we made our first stop at a McDonald's (only thing around) for breakfast and coffee.

Over the next 10 hours or so, we made stops for gas only; bathroom breaks took place at gas stops. We went through the following states with these pictures serving as "highlights":

1. Wisconsin
2. Minnesota
3. (Eastern) South Dakota

Sadly Jake fit in this next picture better than I did due to his name... Maybe one of these days, I'll find a Cameron's of something...

Once we made it to western South Dakota, things became a bit more interesting...

Badlands National Park

Mount Rushmore National Park

From the Badlands and Mount Rushmore National Parks in western South Dakota, we continued for another 7 hours (SUPER long day) to Billings, SD where we would finally be able to call it a day. In total, the day took nearly 20 hours to go 300 miles; needless to say, we were delirious by the time we pulled into the hotel. Here were a couple pictures of the car when we made it:

The emblem on the car was so covered in bugs that it almost appeared the chrome had been burned or damaged in some way. The last 200 miles or so were hands-down the worst for bugs on day 2

In my next post, I'll be going through the next 3 days including our trip through Yellowstone (with camping), Grand Tetons, Jackson Hole, and the journey to Salt Lake City. Here's one quick teaser from our night camping in Yellowstone.