With a 40-pound pack strapped to his back, the wiry then-52-year-old started out from 15th Street in Virginia Beach on June 30, 2014.
“I was complaining to God that no places were being built for the homeless… We care more about housing stray animals in this country, than we do about people,” Bailey said. “He said if you want to build hope centers (for the homeless) around America, you have to walk around America.”
On Wednesday afternoon, more than 8,000 miles through his 11,500-mile trek — one that has taken him through the Everglades, the deserts of the southwest, and the hills of California — he arrived in Racine County, by way of Highway 32.
Landing first at Mocha Lisa Coffee Shop, 2825 4 1/2 Mile Road in Caledonia, he met a customer who put him in touch with local nonprofit Veterans Outreach of Wisconsin. Later the Veterans of America Motorcycle Club in Caledonia put him up in a hotel for the night.
He called the help received here the best community assistance he’s received on his trek that was organized by a church.
A long walk
On Thursday morning, the soon-to-be 54-year-old was sipping coffee once again, this time at Divino Gelato Café, 245 Main St.
Ready to set back out on his track, the contractor and recovering alcoholic took a few minutes to talk about his journey thus far, which has been equal parts grueling and uplifting.
“Basically this is a faith walk. I have no idea what the next city is going to look like. Where I am going to sleep,” he said. “I sprained my ankle in Louisiana. I had stress fractures in my left foot diagnosed in Lordsburg, New Mexico. I had my backpack stolen in San Francisco. I lost my wallet in Seattle.”
But for all the hardships he has suffered, including being turned away by churches in some towns, Bailey has met numerous good Samaritans.
Meeting the homeless
Bailey isn’t the first person to set out on a countrywide trek to raise awareness for the homeless or another cause, but he does believe he is the first person to — as closely as possible given various restrictions — walk the actual perimeter of the U.S. with the goal of helping homeless vets. Bailey, who himself was once homeless, has been working with the homeless for 32 years.
With many nights spent sleeping in the same places where the homeless sleep, Bailey got a sense of how the homeless are treated in communities across the country, from the stifling conditions of a cramped shelter in Florida, to the men he met in Baton Rouge, Louisiana who told him that New Orleans police gave them the option of 90 days in jail or a bus ticket out of town.
His plan is to use any money he raises during his travels to support Servants of God Ministry, which is dedicated to raising money to build homeless shelters across America.
But before he can work building shelters he has to get home. On Thursday afternoon he left Racine hoping to make Zion, Illinois, by supper time. He tries to walk 20 miles a day, he said. From there he plans to walk along the lake, to Grand Rapids, Michigan, eventually reaching Lake Erie and the St. Lawrence Seaway, before crossing Maine, and heading back down the East Coast.
“My wife is hoping I’ll be back home by October,” he said.