A mid-Missouri man who wears several hats, both figuratively and literally, is this year’s winner of America’s Favorite Crossing Guard through SafeKids.org. Lyn Woolford has been a crossing guard at Southern Boone Schools in Ashland for almost six years. He also serves as the city’s police chief, traffic director, city administrator and building code leader.

Lyn Woolford

Woolford tells Missourinet he started as police chief with his goal being to solve a community problem.

“I’m not sure the police department had the greatest reputation in the city. So, I wanted to make some changes. I thought, if I could find a problem and solve it, that would be a good way to introduce what maybe the community could expect from me,” he says.

Woolford set out and then noticed a major traffic headache near school before and after classes. That’s when his school crossing guard career launched.
“I started out just standing in the middle of the street directing traffic so that it would flow efficiently. Then also when the kids were walking to school, we could get everybody stopped and get the kids through the intersection safely. It worked. Once people got to understand to know my signals, everything was pretty fluid,” he says.

Woolford thought he’d take his traffic signaling to the next level by having some fun at the same time. Not only can you find him directing traffic on school days, but you can also find him performing this role while wearing one of his 55 quirky hats.

Woolford started buying hats for different occasions and holidays. Then the townspeople began pitching in. He now has one decorated with a pizza, another with a taco and one with a parrot.

Woolford’s talented police clerk knits quite the hats for him each year. He says two of the most eye-catching ones feature a chicken with the legs hanging down and another is a Viking hat with horns and a beard going down to his waist.

He says his goal was to lighten the mood during what can be a stressful time of the school day.

“It’s really popular with the people, with the kids,” he says. “It’s so much fun to see a car coming and people waving and smiling just because ‘What’s he got on today?’”

Woolford was nominated for America’s Favorite Crossing Guard by a local parent and the community agreed with the move. His hats might have done the trick to put him over the top and win the nationwide contest consisting of 169 nominations from 31 states.

“The community just really came together for me getting their friends to vote and relatives. It probably became a regional vote more than just the community here,” he says.

The top five competitors also had to write a letter and share with the judges why they should win.

The competition was intense. The first and second place winners were separated by only about 50 votes. The runner up has been a crossing guard for 50 years in a much bigger community in Maryland.

“It means a lot to me, that we were able to get this,” Woolford says. “Not only just obtain the money, but the recognition of what a great community that we have here to pull together – a town of 5,000.”

For clinching the top honor, the school district has been awarded $10,000 to use for road safety projects. Woolford’s award is knowing that everyone gets to and from school safely.

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