- December 1, 2022 – Applications available online
- January 28, 2023 – Informational Session
- February 17, 2023– Applications for the 2023 scholarship are due
- March 21 – Upwind 2023 winner(s) announced
- March– Complete third class medical examination
- April 2 – Begin 12 week ground school, Sundays or Tuesdays
- April – Apply for FAA Student Pilot Certificate
- June 12 – Begin flight training, Monday-Friday, 9-5 pm