- November 15, 2020 – Applications available online
- January 30, 2021 – Informational Session
- February 19, 2021– Applications for the 2021 scholarship are due
- March 15 – Upwind 2021 winner(s) announced
- March– Complete third class medical examination
- April 4 – Begin 12 week ground school, Sundays or Tuesdays
- April – Apply for FAA Student Pilot Certificate
- May – Complete discovery flight
- June 7 – Begin flight training, Monday-Friday, 9- 5 pm