Photography courtesy Cannonball Run.
If you were old enough to get into a PG rated movie in 1981, you likely know the name Cannonball Run. The movie featured some of the most interesting cars of its time and a grouping of the “who’s who” of the best movie stars who portrayed characters that were larger than life who laughed all day long and raced against the clock on some of the most scenic roads from coast to coast in the US.
Today, Cannonball Run is known widely as the car rally designed by drivers for drivers, but co-founders Zac and Kelly Dugger are quick to point out to people that the rally isn’t a coast-to-coast illegal race.
The iconic name Cannonball Run was chosen intentionally. The rally draws its meaning from car adventure films of the seventies and eighties. Those films were about people first. Cars mattered, but they served the story rather than driving it.
Zac and Kelly have participated in many rallies. Even large, well-known events often become closed environments once inside. Inner circles form quickly. Others are left on the outside. Kelly was quick to note “the secret sauce was simple to create….we prioritize shared experiences and fun over being spectacle for people to notice.”
When asked why anyone who loves cars and driving should experience Cannonball Run, Zac answered, “We wanted to provide an epic adventure and experience like you’re living in a movie. Our vision was for people from all walks of life to come together and enjoy some of the country’s most incredible scenery and we would travel as a pack driving your favorite car. Your job and your bank balance are irrelevant!”.
Story Before Speed
Driving is how you move through the adventure, not the point of it. This is not motorsport. It is not about speed, times, or results.
Routes are meticulously planned, and participants are chosen with the same care. People come first. The rally is capped at 40 cars. That limit is deliberate. Growth is not the goal. Preserving the experience is. The small numbers allow for safety on the road and close friendships from day one of the rally and every day between rallies.
In the early years, there was still room to experiment around the edges. The first rally extended beyond the drive itself. The group travelled to Cuba via two privately chartered 737’s shortly after it opened to U.S. travelers, building the experience from scratch and navigating international law and logistics in real time. Most rally’s stick to “vanilla plans like driving from a to b” but Zac, Kelly and their team are always thinking outside the box.
The following year, plans were made to fly everyone to a high-end resort in Cancun for a private Steve Aoki show. With payments made, everything carefully planned and the date fast approaching, a late travel warning and mounting security concerns forced a change. Zac and Kelly pivoted fast, and the rally took a detour and instead travelled to a remote ranch in the Badlands of South Dakota, glamping together with all drivers’ cars parked right outside their well-appointed teepees.
A favorite memory of Kelly’s and all participants was “Aoki playing for us and about thirty or forty chicken farmers out in a field. It was a night to remember for sure.”
Another year saw an overturned transport truck carrying pigs that blocked a highway that prevented the rally participants from visiting a resort in Colorado forced a last-minute detour to Vail for the night. Five-star accommodations and a dinner to match were a challenge accepted and expertly executed by the Cannonball team all while they were behind the wheel driving as participants on the rally and all on a moment’s notice.
In 2023, Cannonballers from the US and abroad were treated to a long-awaited visit to Canada that had been on Zac and Kelly’s radar for many years. After a great night in Vancouver, the group headed out on the famous and gorgeous Sea to Sky Highway from Vancouver to Whistler. All participants, even those who had been to Whistler, were in awe of the scenery on the drive to the Four Seasons Whistler. Just a couple days later the group was again treated to a breathtaking stay at the Fairmont Banff Lake Louise. Bucket list hotels and locations are a bonus for all but not the intent.
Zac was quick to point out “It’s hard to put a finger on it. Cool isn’t something you can manufacture. It just exists.”
Roads and Rest
“We came from different car rallies where there wasn’t that family atmosphere—there was a party atmosphere,” Zac describes. “With Cannonball, whether people are new or returning, we create a dynamic organically. The core principle is having a family unit as we rest, relax and drive together.”
Nothing is done to attract attention. When thirty-some-odd cars arrive together, people notice naturally. Gas stations become regrouping points. Locals stop, watch, and take photos. No one manages this. It happens because the group appears where it is unexpected. Drivers exit their cars and talk and laugh about how much fun the last drive was. It’s not uncommon for a stop to take 90 minutes when it might only usually take 20 or so. When the rally launched one year in Lenox, Massachusetts, the entire town came out. Similar moments occur throughout the route.
The route defines the experience. Most of the driving happens on back roads, not highways, through places people usually pass over. Speed and efficiency are not priorities. Exploration is.
Small towns and long, empty stretches are intentional. Famous places and forgotten ones are treated the same. Nothing is ranked or highlighted in advance. Roads are chosen first. Cities, hotels, and logistics are planned for and executed next to support those roads.
Each day ends at a deliberately chosen hotel. These stops are selected for the experience they provide, not convenience alone. Where the day ends matters as much as the drive itself. Kelly happily commented “We have stayed in some amazing and unique hotels over all the years, and the hotels often create the same quality of memories as the drives that got us there”.
Nights are spent together. Shared spaces matter more than private and sterile rooms. The bar usually becomes the center of gravity. “Because we created a community where people enjoy being around each other—and aren’t trying to sell each other—they don’t want to get away from one another after the rally day ends,” Zac notes.
Back in 2024, the rally visited Yosemite in California. Glamping in the Dakota’s was just one of many of Zac’s now famous “Secret Stops”. The drivers saw the Cannonball Run banner on the side of the road and were directed to make a left turn into Autocamp Yosemite. Each participant spent the night in a modern and renovated 31-foot Airstream decked out with a sitting room, bathroom, kitchenette and queen size bed. As cool as the Airstream was, our private dinner that evening was yet another gastronomic delight. As we sat outdoors gazing at a sky filled with stars like never seen before, we were treated to an amazing multi course chef dinner prepared by close friends of Zac and Kelly brought from Oceanside, California.
Short driving days are not uncommon, but Zac described a number of two-night stops along some routes where the group spends their down time in the spa, at a pool or on the golf course.
Continuity and Community
Participants are chosen based on character. Their car does not matter. From the start, they’re treated as part of the group and like family. There is no trial period and no seniority system. Time with Cannonball does not confer rank or authority. Cannonball is not designed as a one-time experience. Most people return year after year.
Before the rally begins, new participants are introduced to the group. It is not uncommon for new participants to meet up with Zac, Kelly or some of their team members between rallies which creates a bond even before people show up to the starting grid. These are not marketing events or sales pitches. They are about community and friendship.
Cannonball is a multi-day drive. You drive with the same people from the first day to the last. There have been many cars made up of lifelong friends, siblings, couples, parents and children. The group moves together. That matters more than how any one person drives.
We communicate, and laugh, over walkie talkies between cars. We all have a route book which lays out the days route and Waze points. And there is a daily minute by minute guide that shows all the day’s activities. All was designed to keep the participants “in the know” but make no mistake, the goal was for Zac and Kelly to make sure the adventure never feels too rigid and structured.
What forms during the rally continues afterward. People stay in touch. They meet in different cities and regions. Cannonball becomes something you return to, not something you complete and discard.
“You get these unique characters—people who are successful but also a bit maverick,” Zac observes. “Over the year, they’re characters in their own regions, and then we all come together.” It is a common occurrence over the alumni WhatsApp channel for someone to write they are travelling to a certain city and whether other alumni live in the same city or people decide to travel there to meet up, the rally family connection carries on.
Cannonball Run recently became a high-profile sponsor at the incredibly popular and well attended Cars on 5th car event in Naples, Florida. A simple message from Zac and Kelly announcing the event turned into a Cannonball reunion of new and past participants who travelled from across North America and as far as Australia.
“We’re focused on community building. It’s not about marketing for signups. It’s about marketing for community. That’s our lightning in the bottle,” Zac adds. “One for all and all for one. It’s never about who you are or what you are.”
Cannonballs partners are limited and long-term. They are chosen for fit, not reach. The rare qualities that the rally and its participants represent are why generous companies like Citi. BRM Chronographs. duPont REGISTRY. Patrón Tequila. Pirelli World Challenge join us. The names matter less than whether they belong.
Cars and their purpose
The joy we get from driving our cars can do good for others in the world aside from the joy they provide us. Cars and their drivers can give back. We never forget how lucky we are to do what we do.
Zac and Kelly always had a vision for charity to be a big part of what Cannonball Run is about. But they wanted to ensure the message was delivered properly to drivers and the community. They wanted to ensure that participants did not feel pressured to get involved with the charity chosen by Cannonball but to instead feel that it makes sense and feels like something they wholeheartedly want to be involved with.
Kelly described the problem to overcome stemmed from the premise of “How do we do this so people are drawn to the charity without feeling pressured? I’ve been to events where money was raised and it went nowhere but a big party.”
With only a couple weeks to go before the start of the 2025 rally, a plan was developed between Cannonball and Make-A-Wish to integrate it into the entire rally. As soon as drivers arrived at registration they were presented with information about the newly formed relationship between the two parties. Cannonball formally kicked off its fundraising efforts at a private dinner in Pittsburgh. What started as a simple pitch turned into laughs, joy, tears and money raised by the generous and impacted group in the room.
A small local dining spot in West Virginia, hosted our group for what was designed to be a short lunch stop. Make-A-Wish invited some Wish families to join us. Three hours later, everyone left with a full stomach but more importantly, the participants left with a better understanding of what joy can be brought to a chronically or terminally ill child and the families that care for these amazing children. It was heartwarming to see these families and kids smile. Even for just a short time.
Long time rally participant and IndyCar racer Santino Ferrucci was having pictures taken with kids. Signing give away items for the families. Kids were given the chance to sit in any cars they wanted to sit in. A little boy shocked the entire group when he mentioned that his favourite vehicle there was the Cannonball Run branded truck pulling a chase trailer in case any participants have issues with their cars.
The impact of that lunch visit propelled the generosity of the group forward at a private dinner at the Greenbriar that same evening. VIP packages for the Indy 500 with Ferrucci as the host, two spots generously donated for the 2026 rally and a few other items were auctioned off. All in all, over $100,000 was raised for Make-A-Wish.
It was clear that the relationship between the parties made perfect sense and proved that the foundation was there to grow the relationship for 2026 and beyond.
“This isn’t a marketing thing. When I think of Make-A-Wish, Cannonball Run is my Make-A-Wish,” Zac admits.
Where to next?
One of our participants loves to tell others that his wife recently asked, “where is your once in a lifetime rally going next.” Another has coined the phrase “it’s the top of your bucket list and you didn’t even know it was on your bucket list.”
If your bucket list includes driving the iconic Route 66….you are in luck. 2026 marks the 100th Anniversary of Route 66 and we are excited to touch a number of stops along this epic stretch of roads as we travel from Chicago to Scottsdale.
