Robert Hillebrand, a bike messenger for nearly a decade, pulled up with his bike to Houston Street before a group of around half a dozen cyclists following him on the tour he was leading.
He pointed to a building, originally called Red Square, that became the first new, luxury building in the East Village complete with a clock with numbers out of order on the roof.
Then he pointed to a statue of Vladimir Lenin on a nearby rooftop, waving, he said, toward Wall Street.
“In the 2000s, they sold building. The new developers took a more normal approach, changed the name to 250 Houston and removed the quirkiness,” Hillebrand, a resident of Flatbush, Brooklyn, said. “They removed Lenin and found a new home for him on a building just across the street.”
In a city with millions of stories, Hillebrand went from bike messenger to a tour guide whose Freewheelin’ Biking Tours has a different message: He re-discovers New York stories and history, gems hidden in plain sight.
“A lot of them were found when I was working on my messenger routes,” Hillebrand said. “Taking an extra minute to explore and see what I might be able to include on a bike tour I was developing.”
In his tour dubbed “Radical and Weird History of New York City,” there’s the small stretch of rail on a rooftop never removed when the High Line was built, a colorful mural about a bus that once routinely broke down while carrying mostly Chinese workers to Boston. Squatters took over a building that is now a squatting museum.
He doesn’t just go to the Gay and Lesbian Community Center in Greenwich Village, but shows the Keith Haring mural in the rest room. His tours take breaks in beautiful community gardens.
“I get a lot of repeat customers,” he said. “I’ve got so many options to choose from. It’s very easy to improvise.”
A licensed tour operator who lists his cycling tour with Airbnb Experiences (and others), his tours start at The Unlimited Biking Shop, 79 Chambers St., that provides bicycles and helmets. They (four hours for $65 including bikes, although sometimes more or less) travel often on bike lanes.
“Technically, my roots are from New York City,” he said. “I’m from Canarsie, but I grew up in Florida. My family moved there when I was two.”
A bike tour in NYC.Photos courtesy of Freewheelin’ Biking Tours
Hillebrand at Broward College, in Florida, got his associate’s degree, working at catering companies and restaurants and becoming interested in cycling, watching documentaries about bike touring, including York City bike messengers, and videos by cyclist and videographer Lucas Brunelle who rode with cameras attached to his helmet.
“I was overwhelmed with school and work full-time,” Hillebrand added. “I figured if I’ m going to be poor, I might as well do something fun.”
When a friend in 2016 said he had a room for rent in Fort Greene, Brooklyn, he moved to Brooklyn. “I decided to experience being a bike messenger in New York City,” he said. “Day one in Brooklyn, I hit up bike messenger companies. The first one I called said they were in need of bikers. They put me to work after meeting with the boss after a half hour. My first day of work was my first day in New York City.”
He had a smart phone with GPS, but no understanding of New York City’s grid, although he learned quickly as a messenger. “I didn’t even have a messenger bag right away,” Hillebrand said. “I got up early and bought a backpack.”
He worked for a company, making minimum wage, or about $300 a week, delivering for print shops, fashion companies, a makeup company, and a herbal dispensary. Gradually, he became part of a messenger scene involving weekend races, standby spots, meeting other messengers, hanging out when he doesn’t have a delivery, and frequenting messenger bars where a lot of messengers go after work
“I was willing to do it, because it paid well,” he said of sometimes delivering pot before it became legal. “Some messengers had nice bikes and messenger bags.”
He then worked for Cycle Hawk, which he said was a well run company that gave bonuses and respected and treated messengers well, and for Clementine Courier, where he made good connections, primarily serving the fashion industry.
“It takes a lot of energy out of you. On my days off, I didn’t really have the energy to do very much,” he said. “I wanted to rest, play video games and not really go out unless it’s for something special.”
He said a co-worker doing weekend bike tours asked if he wanted to try it out, mostly to cover her on vacation.
He started doing tours for Brooklyn Giro, designing tours at the time in Harlem and the Bronx.
“I tried to do tours around holidays, with the theme around that,” Hillebrand said. “I did a Memorial Day bike tour where we went to war memorials and learned about the Battle of Brooklyn and quirky people who built some of the monuments.”
He did a Juneteenth tour on June 19, before it was named a national holiday, as he began to find a niche. Hillebrand in 2020 launched his own company, doing tours such as Governor’s Island where a guest suggested listing on Airbnb Experiences.
“I started networking with other Airbnb Experience hosts,” he said. “They were all doing creative, unconventional tours and having success. I took inspiration from that.
He said Airbnb takes 20% but made his business possible. “How much would I spend on advertising if I didn’t pay that?” Hillebrand said. “They make things very easy.”
The tours sometimes stop outside 97 Orchard St., a kosher butcher shop where women rioted after prices were hiked, and the Triangle Shirtwaist Factory site. They stop at gardens such as La Plaza Cultural-Armando Perez community Garden at 674 East 9th St. They sometimes visit Judson Memorial Church, the Stonewall Inn, Sweet Pickle Books which sells pickles (long made in the area) and books, and a massive amorphous steel sculpture that like a mirror fills with reflections.
They sometimes stop outside a newer-looking townhouse at 18 West 11th St., rebuilt after the Weather Underground blew up a bomb there by mistake.
“That’s one thing I hated, biking in the rain,” he said, noting he’s open to cancelling due to bad weather. “I was forced to do that so many times as a messenger.”
On a recent tour, he biked past famous tourist locations, often heading for more personal, private spots as messengers whirred by as this, slower tour wound through Lower Manhattan.
“We biked straight past so many important parts of New York City to keep the flow of the tour going,” he said.