How would I go about uploading 3 Years of Training rides from Training Peaks to Trainerroad without having to individually upload each ride 
Do you have your TrainerRoad Account setup to sync with your Training Peaks account (in Account → Connections)? I don’t remember how far back TR will sync historical workouts, but I would start with this. Maybe ping support if TR doesn’t pull in all 3 years
I’m in the same boat. The following TR page says it only uploads history automatically from Garmin Connect and Strava: https://support.trainerroad.com/hc/en-us/articles/360003084891-Importing-Activities-Into-TrainerRoad
Hey @Keke_Orth 
Do you have your TrainingPeaks data on Garmin or Strava?