Wineman is a 2013 graduate of Stephens College in Columbia, Missouri, where she earned a Bachelor of Arts degree in theatre.
In June 2006, Wineman entered the Miss Montana's Outstanding Teen pageant and was named first runner-up for the state title.
[9] In January 2010, Wineman won first place for Humorous Solo at the 2009–10 Montana State Drama, Speech and Debate championships.
[3][4] Wineman won the competition on Saturday, June 13, 2015, when she received her crown from outgoing Miss Montana titleholder Victoria Valentine.
[2] Wineman was Montana's representative at the Miss America 2016 pageant in Atlantic City, New Jersey, in September 2015.