Montgomery's innovative work at the Waitsfield Summer School drew the attention of Clark Abt Associates, the famous Cambridge think tank, where he went to work in 1969. Abt's influential book Serious Games from 1970 was an analysis of the effectiveness of role-playing for problem solving, which significantly influenced Montgomery. After leaving Abt, Montgomery subsequently developed a role-playing game for Edison Electric Institute called The Energy Environment Game. The game asked players to assume various roles in a community; all had a stake in the outcome, trying to resolve the scarcity of electricity resources. It was used widely in high schools across the country during the first energy crisis in 1971. Montgomery also designed numerous innovative role-playing programs for training Peace Corps volunteers in cultural awareness and sensitivity. He travelled frequently to West and North Africa during this time to teach Peace Corps trainers for his programs.

 With a young family growing up in Vermont, Montgomery wanted to work closer to home. So he co-founded Vermont Crossroads Press with his first wife, Constance Cappel, in 1975. The press was initially meant to focus on publishing high quality books for young readers. But Montgomery soon found numerous other books worthy of publication. He bought the first political thriller by Doug Terman, The 3-Megaton Gamble, which was pulled from the warehouse before shipping so that Scribner's could officially publish it as First Strike in 1978. He also published The Centered Skier by Automotive Hall of Famer Denise McCluggage.  McCluggage's book mixed elements of sports psychology with Zen Buddhism and became the basis for several skiing teaching programs around the country. Mr. Montgomery also published The Woodburner's Encyclopedia, which became the bible to many in search of alternative energy in cold climates. The title sold over 100,000 copies, which was a signal achievement for such a small press.

In 1977, an author named Ed Packard approached Montgomery about publishing his interactive children's book Sugarcane Island. The young publisher saw it for what it was: a role-playing game in book form, and eagerly agreed to put it in print.  He felt so confident about it that he announced it as the first in a series entitled The Adventures of You.  When Packard left Vermont Crossroads Press to write his next book for Lippincott, Montgomery wrote the subsequent book—Journey Under the Sea—and published it under the pen name Robert Mountain. When his marriage ended in divorce a short while later, Montgomery sold his interest in the press to his ex-wife, and brought "The Adventures of You" to Bantam Books, which was looking for something "different" with which to inaugurate a new children's book division. Bantam offered Montgomery a contract for Journey Under the Sea along with five more untitled books, and renamed the series Choose Your Own Adventure. Little did Bantam or Montgomery realize that a publishing legend was about to be born.  Choose Your Own Adventure went on to sell more than 260 million copies across more than 230 titles in over 40 languages, making it the 4th bestselling series of children's books in the world.

From the first contract, Montgomery opted not to use ghost writers, but to acknowledge every Choose Your Own Adventure author by his or her name. This ran counter to the standard publishing practice of the time of crediting all books to the founding author. This act helped launch the publishing careers of several young authors, including Doug Wilhelm, Jay Leibold, and Laban Carrick Hill, a winner of the National Book Award. He also invited Ed Packard back to write more books, along with Doug Terman, who wrote under the pen name D. Terman. After the first two CYOA contracts, Montgomery shared the writing responsibility for the series evenly with Ed Packard.

"I have edited and published hundreds of children's books, but overseeing CYOA at Bantam was the high point of my long career.  I knew at the time that the series was making a major contribution to literacy, and that was immensely rewarding," notes Ron Buehl, former VP and Editor in Chief at Bantam Books.

Ray Montgomery's interests extended to new technology. He was an early owner of an Apple II. He helped adapt two Choose Your Own Adventure books as games for the Atari console in 1984. Then he was "evangelized" by Apple Computer in 1990 to develop software for CD-ROM on the Macintosh. His most notable project from this era was a creativity tool for kids entitled Comic Creator that he designed and produced with his wife, Shannon Gilligan. Comic Creator was featured as Best New Software in People Magazine in 1995.

Montgomery continued to write books for Choose Your Own Adventure throughout his career. His final title, Gus vs. The Robot King, was released in September 2014. Montgomery and Gilligan took over the series when Bantam Doubleday Dell, now an imprint at Penguin Random, stopped publishing new Choose Your Own Adventure books in 2000. In 2003, they co-founded Chooseco LLC to re-launch the series. Montgomery, who was passionate about education all his life, felt that interactive fiction was critical to reluctant readers in achieving reading fluency, which is the final stage of achieving true literacy. He thus felt it was imperative to keep the books in print. Chooseco has sold ten million copies of 65 CYOA titles in the past nine years.  

A movie based on the series is currently in development at Fox Films. Montgomery is survived by his wife, Shannon Gilligan, of Warren, Vermont, his son, Anson Montgomery, of Warren, Vermont, his daughter-in-law, Rebecca Montgomery, granddaughters Avery and Lila Montgomery and his sister, Joyce Hobson of Portland, Oregon. He was predeceased by his son Ramsey Montgomery III in 2008.

A private memorial was held in the spring of 2015.

Originally appeared in The Valley Reporter on November 19, 2014.

FOR ADDITIONAL INFORMATION:

"Obituary: R. A. Montgomery" in Publishers Weekly

"R. A. Montgomery, 78, Dies; Published Choose Your Own Adventure Series" in NYTimes