Cross-country cyclists, led by ex-cop, ride for pot

Sean C. Morgan

Three men riding bicycles across the country, from Newport to Savannah, Ga., Passed through Sweet Home last week on a quest to promote adventure bicycling and the end of prohibition of marijuana.

Their leader, retired police detective Howard “Cowboy” Wooldridge, has crossed America twice on horseback, from Savannah to Newport in 2003 and Los Angeles to New York City in 2005, a total of 6,400 miles in the saddle. This time he is joined by his brother, Frosty Wooldridge, and friend Wayne Oberding. All are more than 60 years old.

They passed through Sweet Home on April 23.

“I spent the night in Sweet Home with a state trooper, whose wife I met at the edge of town,” Howard Wooldridge said. She was intrigued by his T-shirt, which said, “Legalize Pot.”

“People reacted well to the horse,” Wooldridge said of his previous trips. He is one of about six people who has traveled coast to coast by horse in the 21st century, while thousands have done it on bicycle; and people invariably opened their doors to a cowboy. He and his horse stayed in barns and corrals. Sometimes, he was invited to stay in a house.

“The horse being in a corral was good for the horse,” Wooldridge said. Traveling like that with a horse is much more difficult than bicycling because the horse must be fed, and the rider must think about shelter, water, shoes and injury.

“Now I’m doing another Paul Revere ride,” he said, the opposite way, with a bike.

Why legalize pot?

“We need to do a better job of protecting our children,” he said. “We’re missing pedophiles because they’re flying around in helicopters looking for green plants.”

The black market in drugs gives a job option to youths that is dangerous and kills them, Wooldridge said. That applies across the board.

“At the end of the day, I would end all drug prohibition,” Wooldridge said. They all provide the dangerous job options to youths, and they take away from public safety.

“I emphasize police should be involved with public safety not personal safety,” Wooldridge said. Like shopping or gambling problems, “if you have personal issues, that should be handled by family and friends.”

As a lobbyist with Law Enforcement Against Prohibition in Washington, D.C., for the past six years, that’s a message he repeats constantly, and he insists that drugs should be a 10th Amendment issue, meaning individual states should decide how to handle drugs rather than the federal government – “Let Oregon run Oregon.”

“We’re going to start with marijuana,” he said. “It is demonstrably less dangerous than alcohol.

“In 2003, the message was well-received with exceptions. So far, in Oregon, it’s 100-percent positive.”

National polls passed the 50-percent mark supporting legalization last year, he said. It’s time to do it.

The three are planning to travel about 60 miles per day, completing their trip in two months, Wooldridge said. Most nights, they sleep in a tent. About two nights a week, they splurge, stay in a hotel and get showers.

Frosty Wooldridge is a world-class bicyclist, who has done many trips, Howard Wooldridge said. He has traveled 12,000 miles in South America, including Argentina and Brazil. He rode from Norway to Greece three years ago. He has crossed the United States six times.

“He’s done this, really, all his life,” Wooldridge said. “It’s second nature.”

Frosty Wooldridge, a writer, speaker and adventurer, is encouraging others to live a life of adventure.

“The very, very best part of it is meeting so many good people, kind-hearted, helpful people who help out strangers,” Howard Wooldridge said.

Police officers see the worst, he said, but getting out on the road, he has found that “almost everyone is a good person if you give them a chance to help you,” he said. “To leave that environment and go out to find out the vast majority are good people.”

It’s a “double whammy,” he said, swaying him from the cynical to neutral and then to a positive outlook.

For more information, visit and