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  • Ginny Talley

How Jacking Tires on Pit Road Led to the Ride of a Lifetime

Updated: Aug 16

Charity Rider Len Sherrill relives his days as Kyle Petty’s jackman and details how the Ride was born.

Growing up just down the road from Charlotte Motor Speedway in Kannapolis, North Carolina – home of the great Dale Earnhardt – Len Sherrill was no stranger to stock car racing. He formed an interest in cars and motorcycles early on in life; not only driving them, but also the mechanics involved to make each vehicle the best it could be.

In the late 1980s, Len began his career in NASCAR working for the legendary Buddy Baker. He worked as a fabricator/mechanic and Buddy even taught him how to be a jackman for the race team’s pit crew. From there, Len moved jobs and continued learning the tools of the trade. In 1989, he landed a spot on Crew Chief Gary Nelson’s staff, working on cars for none other than Kyle Petty.

At the time, Nelson’s team was all out of cars due to wreckage. So for his very first task as a new hire, they put Len in the shop all by himself to build a car for Kyle to race at Richmond. According to Len, he “got the car built, but it ended up being wrecked into the wall.” He chalks it up to being a “learning curve” for everyone involved. But it didn’t take long until they conquered those learning curves, as Kyle stood in Victory Lane at the 1990 GM Goodwrench 500 at Rockingham Speedway with Len on his pit crew.


The fun didn’t stop in Victory Lane though. From someone who had his first motorcycle at age 10 and first truck at age 12, Len naturally continued to collect cars and bikes into his adult life. During their time working together, Len purchased a new Harley-Davidson Soft-Tail and Kyle bought a new Harley-Davidson Fat Boy, then Gary wound up getting a motorcycle too. “Looking back, this is kind of where [the Ride] all got started. We just didn’t know it then,” Len said.

Kyle started talking about his idea of riding motorcycles from California back to North Carolina. In 1994, he finally completed a similar version of this idea by riding with a few friends from North Carolina to Phoenix International Raceway for a race. By the time they reached Phoenix, their group had grown to include more than 30 riders. This trip inspired Kyle to think even bigger, and thus, the Kyle Petty Charity Ride Across America was born.

On the very first Kyle Petty Charity Ride in 1995, Len “didn’t even think they were going to make it to the finish.” In fact, the first five years of the Ride were “wide open” and became “a big undertaking.” It was a learning process and a group effort, just like on the race team, to get the Ride off the ground in an organized fashion. In Len’s case, he joined up with Don Tilley and Click Baldwin as the “unofficial mechanic team” for the Ride during the early years before there was any maintenance support from Harley-Davidson. “We would ride all day – some days were 500 or 600 miles – and then pull into the hotel later at night,” said Len. “But Don and Click and I would be up working on bikes until 4 a.m., doing repairs or maintenance so that each bike could continue on the Ride.” And to this day, even though the Ride has service technicians to help with any bike issues on the road, Len still comes prepared and pitches in to help where he can – whether it’s a flat tire or a battery issue or anything in between.

Len might not have originally thought the first Ride was going to be a success, but he was happy to be proven wrong and hasn’t missed a Ride since 1995. In fact, Len is one of just three people who have completed every single mile of every single Kyle Petty Charity Ride Across America! “It’s such a great time with great people and we make the best memories,” said Len. “And when Victory Junction came into play in 2004, then it just all came together – that’s what makes the Ride so special.”


Q+A with Len Sherrill:

1. Is there one specific memory that stands out as a favorite from the Ride?

“The Pizza Party. This actually started either the first or second year of the Ride. We had run all day and got into the motel late, so we just ordered a bunch of pizza and pulled out some beer right there in the motel parking lot. Out of all my memories from the Ride over the years, that very first pizza party was one of my favorites – everyone just came together after long, hard day to sit back and relax together.”

2. What is your earliest memory of motorcycles?

“Growing up, everyone else had dirt bikes when were kids, but my very first motorcycle was a Harley-Davidson – and I still have it. But, in 1973 I bought my first Yamaha with the help of my dad. He told me if I could come up with half the money, that he would pay for the other half.”

3. How many motorcycles do you currently own?

“I have 14 and they’re all Harleys.”

4. How would you describe the Ride to someone who has never heard of it before?

“You really can’t describe how much fun you’re going to have on the Ride. And you’re going to get hooked. I don’t know a single person who hasn’t gotten hooked on the Ride after doing it just once.”

5. What does it mean to you to be able to ride for the kids at Victory Junction?

“You just can’t beat that smile on those kids’ faces and the way they light up. You just can’t.”