Equitation is a cause of physiological stress in the equine athlete, and personality is a factor generally associated with the different responses of equines to stressors. This study explored ocular temperature, measured via infrared thermography, associated with personality and stress in horses submitted to dressage exercising in riding lessons, ridden training and lunging. Infrared thermograms of 16 horses were taken before and after sessions using an FLIR F4 camera (FLIR Systems AB, Sweden) to determine maximum eye surface IRT temperature (IRTmax), and total training time was registered (T). A novel-stimulus test was conducted for personality assessment, and the ridden behavior was scored (mRBS). The results showed that T was statistically different (p ˂ 0.001) between modalities, but no differences were found in any IRTmax tests. Statistical correlations were found between mRBS and personality groups, sex and age (all p < 0.001). Additionally—and with caution, given the sample—no association was found between mRBS and post-workout IRT readings and modality, or between pre-workout IRT readings and personality groups. We conclude that trained horses show little stress when working in a familiar environment and when the workout plan is submaximal. The personality test was adequate and positively correlated with ridden behavior.