Before teaching Jazz and Concert Band for 34 years, Keith Woolery found his own niche on the road. Touring for years at a time, Woolery believes he has enough stories about life on the road to write a novel.

After college, Woolery and his wife Donna began a new adventurous chapter–‘The Keith Woolery Show Band.’ Multiple other members filtered in and out of the band, and most had the ability to play a multitude of instruments. Donna herself could be known to play the trumpet and the keyboard simultaneously.

For years on end, The Keith Woolery Band would travel 49 to 52 weeks per year, playing a various set of show tunes five or six times a week.

“We spent a lot of nights just driving all night, covering 800 miles or so. That was not unusual. We lived in hotels or Donna and I would stay in our trailer with our dogs. With the type of places that we were performing we could spend a month somewhere or just a day,” Keith said.

Within their travels, ‘The Keith Woolery Show Band’ covered 39 states and also performed in Canada. The group played a variation of genres, but while in the South Padre Island, chose a diverse range of music that appealed to their audience.

Eventually, the couple wanted children and they decided life on the road was no longer the best fit for them. While in search of a place to settle down, Woolery was offered a teaching position at Newton High School.

“If you didn’t have children [life on the road] would be great. That was the reason we got off the road. We had watched other people attempt to do that and nobody was really successful,” Woolery said. “An opportunity came up to come to Newton High School so I did and Donna followed a year and a half later.”

After this year, Woolery will be leaving behind his students and the life he had while teaching. Woolery feels that he’s made a lasting impact on many students he has taught, and feels that his retirement does not quite fit the classic example.

“I’ve been thinking that out of all my stories from on the road I should write a book. From playing in clubs that were overrun by the mafia and being kicked out of Canada. We just had a lot of interesting experiences,“ Woolery said.

Even after so many years Woolery has said that he doesn’t regret anything regarding his teaching career.

“I haven’t ever had to work for a living so that’s pretty cool. I’ve been getting paid to do something I enjoy doing.”