Tramp art seems to have sprung up in America and Europe at the roughly same time, though the carving technique—known as chip carving—had been used in Europe for centuries. Using a pocketknife or other sharp tool, the untrained artisan would whittle away small wooden chips and, using glue or nails, layer the chips into shapes, such as hearts or stars. Clifford A. Wallach, a dealer who has written three books on the subject including the just-released A Legacy in Tramp Art, says that the artists had plenty of material to work with: from 1870 through the 1930s, over 100 million cigar boxes were sold annually.

The name Tramp Art–coined in the U. S.—is also a misnomer. "The term originated in 1959, with the publication of Frances Lichten’s book Tramp Art: Penknife Plus Cigar Boxes," explains antiques dealer Emanuel Bouqvar, of E & L Alexandria, in Brookhaven, New York. "Lichten noted that while tramps, hobos and other itinerants did make edge-carved works, research has shown that most pieces were made by hard-working people who lived non-wandering lives. After all, in the age before television, after a hard day’s work, it was nice to come home and whittle for fun!"

Tramp art typically came from industrialized areas, like Pennsylvania and New York, where winters were long and cold—it was men’s equivalent to quilting. Dealer John Sholl estimates that one work, a car made of 5,659 pieces of cigar box wood, took 1,016 hours to make.

Judy Pearce of Alpen Antiks, in Aspen, Colorado, notes that many of the "artists were immigrants from Germany and Austria. They worked their way here during the early twentieth century, bringing their craft with them. I find all of my tramp art pieces in Europe."

Today, the most easily found (and least expensive) collectables are frames; photography was just coming into vogue when the art was at its height. Prices vary widely, with elaborate pieces, such as mirrors, clocks and cabinets, fetching prices that are definitely not in tramp territory. "Pieces have sold for as much as $98,000 at auction," says Bouqvar.