- The first Westernaires class, in 1949, was 36 riders. By the early 1960s, the new "Tenderfeet" (inductees just joining) classes were over 200 riders in number, and the overall membership numbers each year averaged around 1,000 members. Today's membership averages between 1,200 to 1,500 members each and every year.
- Westernaires once owned a Guiness Book of World Records record for the largest pyramid on horseback (the Westernaires "Riders of the Steppes" cossack-type trick riders).
- The Westernaires Varsity Big Red Team has over 1,000 costume combinations that they can choose from -- they rarely hit an arena in the same costume combination twice.
- Among myriad other events across North America, Westernaires has performed at the Trinidad Roundup Rodeo (Labor Day) each year since 1958. (The Varsity Big Red Team, along with various specialty acts.).
- Westernaires Varsity Big Red Team was selected above all other drill teams in North America to ride for a film shot by the Horse Museum of France in "Horse Troops of the World". The segment was called "Westernaires Carousel".
- The Westernaires organization was given the "Physical Fitness Award" by President Eisenhower -- the second organization to ever receive this award.
- Normal Rockwell, Artist and Illustrator, said: "Coloradans have tremendous vitality and energy. They all seem to be athletes. Great horsemen, too. The Westernaires provided a whole Cavalry troop for a movie that I was working on in Colorado a few years ago. During the filming they put on a show for us. The jumping and formation riding was really spectacular.".
- In 1958, the Westernaires formally established a Museum of Horse and Driving History. The museum has grown to one of the western highlights of the state of Colorado. It is used not only for their members' learning, but serves as a value and attraction for nearby public schools as well. The museum contains one of the most complete displays of western saddles. The museum earned Westernaires a "National Historical Award" for promotion of a better understanding of western history.
- Since the early 2000s, the Westernaires Varsity Grand Entry team appears at the National Western Stock Show in a darkened arena in illuminated, dramatic costumes on both horses and riders.
- In 1949, the Youth Council of Lakewood, Colorado came to Mr. Elmer E. Wyland (then a telephone company executive), asking that he organize an activity on a year-round basis whereby young people of the Jefferson County area could learn to ride horses and learn about how to live in the western tradition. Wyland, along with his wife Marjorie, was selected since he had trained mixed adult riding teams as a hobby. The Commission stressed that the organization must be a non-profit for both boys and girls, have no paid employees, and provide activity to take up any slack time for the members all year. Full cooperation was given by of all the civic and lodge groups in the area at the time.
- Westernaires turns out more high-level, skilled trick and fancy riders than any other organization on the planet. Many of these members, after graduation, go on to perform professional stunt work.
- Westernaires has graduated thousands of members since its formation in 1949. Many of these alumni come back to Westernaires to volunteer as instructors, wranglers, mechanics, drivers, etc.
- Westernaires founder Elmer E. Wyland was named Man of the Year by the Jefferson Sentinel in 1961. He published numerous books, magazine articles, and newspaper article.
- The Westernaires organization was given the Centennial Commission Award in 1959 for promoting Colorado.
- Westernaires was nominated by Jefferson County Schools for the "Valley Forge Award" for their work in the community.
- Westernaires youth activities have been given the highest tribute by being read into the Library of Congress (Congressional Record) twice: by Colorado Representative Donald G. Brotzman on March 14, 1968; and by Colorado Representative Timothy E. Wirth on May 7, 1975.
- Westernaires has performed at the National Western Stock Show and Rodeo (every January) annually since 1952. They perform a Grand Entry act and a feature act for nearly every PRCA rodeo during the 2+ weeks of the event.
- Westernaires have been appointed as Envoys to Good Will to other states by the Colorado Governor on over a dozen occasions.
- The Westernaires organization was given the American Legion Award in 1959 for their promotion of Colorado.
- The Westernaires organization was given the National Historic Award in 1963.
- In 1978, Westernaires founder Elmer E. Wyland received the John F. Kennedy medal "In recognition for outstanding service," also known as the Jefferson Award by the Institute for Public Service.
- In 1970, Westernaires received a telegram from President Richard Nixon: "In recognition of your principals and lifelong effort to further the American way of life and free enterprise." (Also reported in the Denver Post in February 1970).
- In 1978, Westernaires received congratulations from President Jimmy Carter, in person, for 30 years of volunteer service to youth.
- In 1961, President Dwight D. Eisenhower sent a letter of appreciation (presented by TV personality Ted Mack) to Westernaires and founder Elmer E. Wyland.
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