OBJECTIVE To test the hypothesis that greater chocolate-candy intake is associated with more weight gain in postmenopausal women. DESIGN AND METHODS Prospective cohort study involving 107,243 post-menopausal American women aged 50–79 years (mean=60.7) at enrolment in the Women’s Health Initiative (WHI), with three-year follow up. Chocolate-candy consumption was assessed by food frequency questionnaire and body weight was measured. Linear mixed models, adjusted for demographic, socio-economic, anthropomorphic and behavioral variables, were used to test our main hypotheses. RESULTS Compared to women who ate a 1 oz (~28 g) serving of chocolate candy <1 per month, those who ate this amount 1 per month to <1 per week, 1 per week to < 3 per week and ≥3 per week showed greater three-year prospective weight gains (kg) of 0.76 (95% CI: 0.66, 0.85), 0.95 (0.84, 1.06) and 1.40 (1.27, 1.53), respectively, (p for linear trend<0.0001). Each additional 1 oz/day was associated with a greater three-year weight gain (kg) of 0.92 (0.80, 1.05). The weight gain in each chocolate-candy intake level increased as BMI increased above the normal range (18.5–25 kg/m2), and as age decreased. CONCLUSIONS Greater chocolate-candy intake was associated with greater prospective weight gain in this cohort of post-menopausal women.