- December 1, 2023 – Applications available online
- January 27, 2024 – Informational Session
- February 16, 2024– Applications for the 2024 scholarship are due
- March 18 – Upwind 2024 winner(s) announced
- April 7 – Begin 12 week ground school, Sundays or Tuesdays
- April – Apply for FAA Student Pilot Certificate
- June 10 – Begin flight training, Monday-Friday, 9-5 pm