Blessitt was born in Greenville, Mississippi, and grew up in northeast Louisiana, where his father managed a large cotton farm. At the age of 7 he accepted Christ at a revival meeting. In the late 1960s Blessitt began evangelizing to the youth of Hollywood, California. There he became known as the "Minister of Sunset Strip." Blessitt preached to hippies, Hell's Angels, runaways, drug addicts, teen prostitutes, flower children, would-be actors, and rock stars. In March 1968, he opened a coffee house called His Place in a rented building next door to a topless go-go club.
His first marriage was to Sherry Anne Simmons, whom he married within three weeks of dating. Together they had six children: Gina, Joel, Joy, Joshua, Joseph and Jerusalem.
In 1990 he married Denise. They have one child, Sophia. As of the late 2000s, he lives in Denver, Colorado.
On Christmas morning in 1969, Blessitt began his journey with the cross, walking from Los Angeles, California, to Washington D.C. In August 1971, Blessitt began his journey around the world, beginning in Northern Ireland.
He has carried the cross to all parts of the world including war-torn countries such as Lebanon and parts of Africa to pray for peace. During the Cold War, Blessitt carried his cross into the Soviet Union, through Russia, the Baltic States, Ukraine and other countries. He has carried the cross through such places as Iraq, North Korea, Iran, Afghanistan, Somalia, Sudan, China, South Africa, Lebanon, India, Antarctica, Palestine, Israel, Cuba, Libya, Yemen, Vietnam and Mongolia.
During his walk around the world, Blessitt has held audience with numerous world and religious leaders including, Jimmy Carter, Reverend Billy Graham, Pope John Paul II, Yasser Arafat and Muammar al-Gaddafi and was arrested 24 times (not for crimes).
On part of the crosswalk through Beirut, Blessitt chose to bring his son Joshua.
He completed his journey on June 7, 2008 and he is listed in the Guinness World Records for the "World’s Longest Walk."
In total, Blessitt has walked 38,102 miles through 315 countries (including Island Groups and Territories), of which 52 were in open war. He has crossed every ocean and walked on all seven continents (including Antarctica). He is known internationally as the "Pilgrim with the Cross."
Blessitt is the subject of a 2009 documentary feature, The Cross: The Arthur Blessitt Story, directed by Matthew Crouch. Christianity Today was critical of the movie, identifying:
Because Crouch avoids any deep questioning of Blessitt, and fails to bring in any other voices, The Cross lacks structure. While Blessitt is appealing, once the novelty of his walk wears off, there's nothing left for audiences to sink their teeth into.