The track was 4 miles from his house.
So each Saturday morning, along with some friends and later one of his brothers, Childress walked.
The boys took a circuitous route, often stopping by one of the local auto shops that was preparing a car for the evening's races. They always got to the track early, before the gates opened, and in that way saw a lot more than what was on the evening schedule.
"They'd open the gates at about 4 o'clock," Childress said, "but the drivers would be lined up there outside, waiting to get in. They'd be drinking whiskey, having women, all the crazy things that went on back in the day. And I said: 'Hell, that's not a bad lifestyle. These guys are having fun.'"
While most customers at the track ended up lighter in the wallet coming out than they were coming in, Childress did not. He found a place that you could sometimes jump the fence and get in to the races without paying. Or, more frequently, he would simply find a couple paying to get into the races and "adopt" them for about five seconds, because children got in free with an adult.
"Whatever it took to get in, I did," Childress said.
On that first night with his stepdad, he saw young kids much like himself hawking peanuts and popcorn to the fans.
Was this a job he could do? It was.
"They would pay you a penny a bag to sell peanuts and 2 cents a bag for popcorn, because the popcorn was bigger and you couldn't carry as much," Childress said. "If you went out there and made a dollar, that was good money."
That was the beginning. Childress watched those races in between his sales and dreamed of becoming a successful driver himself. And he became a driver, all right, but not the sort that goes into any sort of hall of fame.
Childress dropped out of school after the ninth grade and worked to help support the family. At age 18, in 1963, he bought a 1947 Plymouth cab and souped it up. "Best investment I ever made," Childress said. He raced at shorter tracks but wanted to become a driver on NASCAR's top circuit, then called the Grand National Series.
By 1969, Childress wasn't running the taxi anymore but still was a struggling driver who didn't have enough money or good enough cars to run at the highest level. But he caught a break when most of the top drivers participated in a boycott in 1969 after there were safety concerns when a new racetrack opened in Talladega, Ala., and tires kept shredding on its steeply banked turns.
Bill France Sr. was determined that the race would be run, however. "Big Bill" recruited a number of substitute drivers, including Childress, who had driven a preliminary race the day before.
Childress finished a modest 23rd, but France had promised extra money to every "replacement" driver who ran the race and made good on it.
"It was a turning point in my career, Childress said. "I left with enough money to go back, buy a little piece of land and build my first shop. ... It was a garage, and I opened it up working on public cars and my race cars."
By age 27, Childress was a full-time driver in NASCAR's top series, just as he had hoped. The problem was that he never won. Ever. A few top teams won most of the races, and Childress had neither the equipment nor the driving talent to compete. He would start 285 races in his career and not win a single one.
He did, however, win an invitational race once at a smaller racetrack that produced abundant fruit. Among the men he beat in that race was a young Dale Earnhardt, who came up to Childress afterward, jabbed a finger into Childress's chest and promised he would beat him the next time.
"Oh, and he did," Childress said. "And every time after that, too."
In 1981, Childress got out of his race car for good and put Earnhardt in it for the final 11 races of the season. He quickly understood that Earnhardt was a far better driver than he was, but they didn't win a race that year. In 1982, the two went their separate ways again – Childress said he told Earnhardt to take another opportunity because Richard Childress Racing wasn't good enough to employ him full-time yet.
The two kept hunting together and talking about working together again, though, and in 1984 they did. They would end up winning six championships together at NASCAR's highest level –– Earnhardt had won one before he began driving for Childress.
Their iconic No. 3 black Chevrolet became famous worldwide.
"He and Earnhardt were the standard," said fellow NASCAR owner Rick Hendrick of Childress. "When I first started, I didn't think anybody would beat them. They were unbeatable."
Earnhardt died in a last-lap crash in the 2001 Daytona 500, a day Childress still finds painful to talk about.
"There isn't a week that goes by that I don't think about it," Childress said. "It used to be every day. Time heals, but you never forget."
Childress has kept going, though. Grandsons Austin and Ty Dillon are both up-and-coming drivers in the sport that drive for Richard Childress Racing. Now 71, Childress remains feisty. In 2011, Childress angrily punched driver Kyle Busch after a dispute at a racetrack. Childress got fined $150,000 by NASCAR.
"If I had that to do over again, I would have handled myself a little different probably," Childress said.
And although Childress is now also in the wine business and has become rich beyond his wildest dreams, he still remembers the value of a single dollar earned selling popcorn and peanuts. And he teaches the lesson occasionally to those who don't understand it.
Once in the late 1990s, Childress recalled, he owned two planes. Each transported his race teams in style to the track each week, but one of the planes was a King Air that wasn't as fancy as the other. Mike Skinner's race team was assigned to the King Air, and after awhile some team members weren't too happy.
"These guys were with Skinner's team and were complaining about flying," Childress said. "So I met them at the airport one morning and they said 'Where's the plane?' I said: 'Jump in – we're going to drive to Dover.'"
Dover was the site of that weekend's races. It is in Delaware, about a 450-mile drive from Charlotte.
"After that," Childress laughed, "they were happy to be back in a King Air."