In this paper, we examined glass transition, a very important parameter that determines the properties and applications of epoxy resins by the innovative approach of kinetic study. The effect of thermoplastic filler Polyethylene Glycol-1000 (PEG-1000) on the kinetics of glass transition temperature of epoxy was analysed by varying the filler loadings and the heating rates. The differential scanning calorimetry curves were plotted at heating rates of 5, 10, 15 and 20°C, respectively and the kinetics of glass transition by varying the heat rates was investigated. Kissinger and Moynihan methods were employed to analyse the glass transition kinetics. The changes in glass transition have been interpreted remarkably with the constrained polymer region of the systems. The improvement in toughness of about ≈ 213% was obtained compared to the neat epoxy with an addition of about 1 wt-% of PEG loading. The toughening mechanisms were elucidated by analysing the scanning electron microscopic images of fractured samples.