Landfair first gained notoriety in 2006, amidst an indefinite nationwide odyssey. Pawning all he owned, including his 2005
College World Series ring, he purchased a 1995
Suzuki Intruder 800
motorcycle he did not know how to ride, and left with "no route, no budget, no clue." At first sleeping outside, he worked as a manual laborer, eventually crossing all forty-eight contiguous states. During his time on the road, he legally changed his name to
Woodrow, stayed in two New York City
homeless shelters, worked for cash with
illegal immigrants, and spent over a month living within the
Anarchist group
Common Ground Collective in New Orleans's
Lower Ninth Ward after
Hurricane Katrina. Among other odd jobs, he worked as a
day laborer, a swimming pool
lifeguard, a bouncer, a truck driver, a door-to-door salesman, a beverage delivery man, a stagehand, and a waiter for an Italian restaurant with ownership ties to the
Gambino crime family. Landfair used the jobs as material for oral stories. Between traveling and working, he began self-promoting in roadside bars and coffee shops where he talked about his hoboing experiences. He developed a storytelling act, eventually appearing in theaters and on regional and nationwide television. As of May 2007, he had reached thirty-two states, performing oral stories in forty-one cities. He was featured in several newspapers nationwide and on May 8, 2007 appeared on the front page of the
Austin American Statesman as part of a two-page spread. On September 23, 2007, Landfair authored and performed a
one man show 48 States of Adventure at Washington D.C.'s
Wolf Trap National Park for the Performing Arts in front of a capacity crowd. The show was recorded as an album, 48 LIVE, which sells on iTunes. On September 24, 2007, the
Fox News Channel ran a feature on Landfair, his stories and his travels. Anchor
Shepard Smith referred to Landfair as aspiring to become "the next John Steinbeck or Louis L'Amour." From 2007-2008, he published articles as associate editor of Prop. 65 Clearinghouse in San Francisco, then joined the production staff at New York City's
The Public Theater in 2009. With approval from the
US State Department, Landfair left New York in 2010 to join an American delegation in
Havana,
Cuba. ==
Land of the Free==