Born in South Bend, Indiana, Kaufman started birding from the age of six. When he was nine, his family moved to Wichita, Kansas, where his fascination with birds intensified. At age sixteen, inspired by birding pioneers such as Roger Tory Peterson, he dropped out of high school and began hitchhiking around North America in pursuit of birds. Three years later, in 1973, he nearly set the record for the most North American bird species seen in one year (671) while participating in a Big Year, a year-long birding competition. However, this record included regions like Baja California that are no longer ornithologically considered part of North America and has since been surpassed. His cross-country birding journey, covering some eighty thousand miles, was eventually recorded in a memoir, Kingbird Highway.
Kaufman resides in Oak Harbor, Ohio with his wife Kimberly. Today Kenn writes for Birds and Blooms,Bird Watcher's Digest, and works/volunteers at the Black Swamp Bird Observatory. Kaufman maintains a weblog where he reports bird sightings in the northwest region of Ohio and makes predictions about the spring bird migration.