Pittsburgh Youth Leadership

In 2005, Mark Rubenstein went on a long distance bike trip with his then 13-year-old son. It was a life-changing experience, one that widened his son’s view of the world and strengthened their relationship. One year later, Rubenstein founded Pittsburgh Youth Leadership (PYL), with the mission to give the same experience to inner-city kids.

This summer, PYL celebrates its 10th year and on June 14 the 62-year old lawyer, along with three other mentors, will take nine kids on a 39-day, 3,000-mile cross-country trip on bicycles. It will be the longest trip in the organization’s history.

The group will fly to Oregon to pedal from the Pacific Coast to the Atlantic Coast at the Jersey shore. The kids—ranging from 8th grade to freshman in college—will travel through Washington, Idaho, Montana, South Dakota, Nebraska, Iowa, Illinois, Indiana, Ohio, New York and Pennsylvania before reaching the finish line in New Jersey.

“Over the last 10 years, we have taken about 70 kids on long-distance bike trips. They are usually about 2 weeks and average about 600 to 800 miles,” Rubenstein says. “This distance is a first for us.”

PYL recruits kids mostly by word of mouth, reaching out to schools, churches and community centers. But Rubenstein says it has not always been easy for PYL to find participants, even though they offer an all-expense paid trip. “Maybe because it’s a foreign concept,” he speculates.

“The kids who go with us—by and large—have an extremely limited vision of a future because their experiences are limited by economic circumstance. A bike trip with us may be the first time they experience anything outside of Pittsburgh. We biked to the ocean several times, and for many kids, it was the first time they saw the ocean.”

Diondre Farris, who has been on one of the rides, says that seeing other states and traveling with different people have opened his eyes to the world. “There is so much more than what I can see everyday. What I wake up to everyday.”


There are no qualifications required to join PYL, except perhaps a willingness to give the challenge a go.

“When we first told the kids what they would be doing, they thought it would be impossible. But all the kids have prevailed—this shows them that they can do anything they set their mind to.” This ambition and the pursuit of one’s potential are values that Rubenstein hopes to instill.

Over the years, PYL has taken kids to bike trips through many of the country’s most scenic regions, including the Everglades and Key West, the Blue Ridge Mountains, the Outer Banks, the Rockies, and Big Horn Sheep Canyon. The training regimen for the trips is difficult—but short, on average only three to four days.

“Ten years ago, I trained some kids too hard on a really hot day and they were crushed,” shares Rubenstein. “I thought I made a really huge mistake but they all came back the following week.

“The training days are brutal because I would rather find out that they don’t want to do it while we are still in Pittsburgh rather than in Montana,” Rubenstein adds.

“It is funny that people view these kids as super cyclists—with the rare exception, none of them have ever biked beyond the two miles around their neighborhood,” says Rubenstein. “They may not necessarily be the best cyclists but they are kids with a positive attitude, kids who want to do something. Cycling is secondary to character.”

And while cycling takes a back seat to attitude, kids develop their skills on the job. “The kids get better as the trip goes on. They are tired but their biking muscles get better, they learn how to use gears better, how to bike more efficiently,” notes Rubenstein.

“Over the years, the kids have just gotten really good—its kind of scary. In the past, we’ve gotten kids who just want to see the world. Now I have these kids who are really into cycling and it is challenging for me.”

It used to be challenging because he had to be so patient and encouraging, he says. Now? He has to tell them not to give me a hard time for being so slow.

PYL takes about eight trips a year and in a decade, participants have biked 137,000 cumulative miles across 44 states.

“We’ve had a wide range from kids—some go on a trip and may not keep in touch and some stay with us throughout their youth,” says Rubenstein. “We do our best to mentor, to keep in touch.”

With some self-deprecation, Rubenstein adds, “Sometimes it works. About 12 kids who participated were first in their family to go to college.”

In PYL’s video for this summer’s Conquering the Cycle, Cody Wagner talks about moving to Pittsburgh after his mother passed away and the impact the trips have made on him. “Back then I really didn’t see myself living past the age of 17. These trips gave me a new light, taught me how to become a man, set goals and achieve them.”

Mentchaas Anderson only has encouragement for kids who may think this is isn’t something they can do. “If anyone has the opportunity to do something amazing, or something that you might think you may not even enjoy—don’t knock it until you try it. It could change your life. Like these trips have changed mine.”

Leah Lizarondo is a food advocate, writer and speaker. She is also the co-founder of 412 Food Rescue, an organization that seeks to eliminate food waste to make an impact on hunger and the environment. She is the Chief Veghacker, recipe creator and curator at The Brazen Kitchen, where she writes about food and food policy. She writes about the intersection of food, health, innovation and policy.