In 1931, when Okemah's boomtown period went bust, Woody left for Texas. In the panhandle town of Pampa, he fell in love with Mary Jennings, the younger sister of a friend and musician named Matt Jennings. Woody and Mary were married in 1933, and together had three children, Gwen, Sue and Bill.

It was with Matt Jennings and Cluster Baker that Woody made his first attempt at a musical career, forming The Corn Cob Trio and later the Pampa Junior Chamber of Commerce Band. It was also in Pampa that Woody first discovered a love and talent for drawing and painting, an interest he would pursue throughout his life.

If the Great Depression made it hard for Woody to support his family, the onslaught of the Great Dust Storm period, which hit the Great Plains in 1935, made it impossible. Drought and dust forced thousands of desperate farmers and unemployed workers from Oklahoma, Kansas, Tennessee, and Georgia to head west in search of work. Woody, like hundreds of “dustbowl refugees,” hit Route 66, also looking for a way to support his family, who remained back in Pampa.

Moneyless and hungry, Woody hitchhiked, rode freight trains, and even walked his way to California, taking whatever small jobs he could. In exchange for bed and board, Woody painted signs and played guitar and sang in saloons along the way, developing a love for traveling the open road—a lifelong habit he would often repeat