One of the five co-founders of the New York Village Voice, Wilcock shook up staid publishing in the USA. His influences extended to several continents, including Australia and the United Kingdom, where—in his mild-mannered way—he pushed the boundaries of image and speech. An unsung hero of the sixties,  Wilcock also served three years as a travel editor at The New York Times.
While coordinating the Underground Press Syndicate (200 papers worldwide), he guest-edited "underground" papers in London, Los Angeles, and Tokyo, returning to New York to publish his own underground tabloid, Other Scenes.
In 1960 Wilcock wrote the first of several travel books for Arthur Frommer, Mexico On $5 a Day, following up with guides to California, Greece, Japan, and India. During this period he co-edited (with Elizabeth Pepper) The Witches Almanac. Three more books resulted from their collaboration: Magical & Mystical Sites (Europe); an Occult Guide to South America, and A Guide to Occult Britain. At the invitation of the Venezuelan government he researched and wrote Traveling in Venezuela in 1979 and, in the 1980s and 1990s wrote/edited 25 books for Insight Guides.
During a five-year association with Andy Warhol, Wilcock audiotaped the enigmatic artist's closest associates, asking them to "explain" him, publishing the results in 1971 as The Autobiography and Sex Life of Andy Warhol. This $5 biography became a rare book offered for sale on Amazon at prices close to $1,000. A revised edition of the book was released in 2010.
Relocating to Ojai, California, in 2001, Wilcock began publishing an international monthly magazine, the Ojai Orange, free to his friends in a dozen countries, and all issues of this are now available on his website, along with his weekly column (now in its 51st year) and his weekly public-access television travel show.