Background: Plantar fasciitis is a leading cause of heel pain and is commonly linked to prolonged standing, altered foot biomechanics, and increased body mass index. Teachers are especially susceptible due to extended standing during teaching activities. Despite this, there is limited local evidence on the prevalence of plantar fasciitis and its contributing factors among medical college teachers in India. Aim: To assess the prevalence of plantar fasciitis and identify its associated factors among teachers of a medical college in Jalgaon city. Methodology: A cross-sectional observational study was conducted involving 52 teachers aged between 24 and 60 years at a tertiary healthcare institution in Jalgaon. Participants were selected through convenience sampling according to predefined inclusion and exclusion criteria. Data collection comprised demographic details, daily standing duration, body mass index (BMI), Windlass test outcomes, and pain intensity measured using the Numerical Pain Rating Scale (NPRS). Statistical analysis was carried out using SPSS software, with associations analyzed through the Chi-square test. Results: Plantar fasciitis was identified in 51.92% of participants based on positive Windlass test results. The mean participant age was 29.96 ± 3.75 years, and females represented 75% of the sample. A significant association was observed between longer standing duration and positive Windlass test findings (p = 0.048). Pain severity, as measured by NPRS, demonstrated a highly significant association with plantar fasciitis (p < 0.001). No significant associations were found with age, gender, or BMI. Conclusion: This study reveals a high prevalence of plantar fasciitis among medical college teachers in Jalgaon, with prolonged standing identified as a major contributing factor. The findings highlight the need for early screening and preventive interventions, including ergonomic adjustments, adequate rest intervals, and the use of supportive footwear, to minimize the impact of plantar fasciitis in this occupational group.