Over the past two decades, the once small local Colorado Springs Mathematics Olympiad, founded by the author himself, has now become an annual state-wide competition, hosting over one-thousand high school contenders each year. This updated printing of the first edition of Colorado Mathematical Olympiad: the First Twenty Years and Further Explorations offers an interesting history of the competition as well as an outline of all the problems and solutions that have been a part of the contest over the years. Many of the essay problems were inspired by Russian mathematical folklore and written to suit the young audience; for example, the 1989 Sugar problem was written as a pleasant Lewis Carroll-like story. Some other entertaining problems involve old Victorian map colorings, King Arthur and the knights of the round table, rooks in space, Santa Claus and his elves painting planes, football for 23, and even the Colorado Springs subway system.The book is more than just problems, their solutions, and event statistics; it tells a compelling story involving the lives of those who have been part of the Olympiad from every perspective.