Background Three recent meta-analyses found significant prospective inverse associations between chocolate intake and cardiovascular disease risk. Evidence from these meta-analyses suggests that such inverse associations may only apply to elderly individuals or those with pre-existing major chronic disease. Objective We assessed the association between habitual chocolate intake and subsequent incident coronary heart disease (CHD) and stroke, and the potential effect of modification by age. Design We conducted multivariable Cox regression analyses using data from 83,310 postmenopausal women free of baseline pre-existing major chronic disease in the prospective Women's Health Initiative cohort. Chocolate intake was assessed using a food-frequency questionnaire. Physician-adjudicated events or deaths were ascertained up to 30 September 2013. Results After exclusions, there were 3246 CHD and 2624 stroke events or deaths, representing incidence rates of 3.9% and 3.2% during 1,098,091 and 1,101,022 person-years (13.4 y), respectively. We found no association between consumption of chocolate and risk of CHD (P for linear trend = 0.94) or stroke (P = 0.24). The results for CHD and stroke combined were similar (P = 0.30), but were significantly modified by age (P for interaction = 0.02). For women age <65 y at baseline, those who ate 1 oz (28.35 g) of chocolate <1/mo, 1 to <1.5/mo, 1.5 to <3.5/mo, 3.5/mo to <3/wk, and ≥3/wk had HRs (95% CIs) of 1.00 (referent), 1.17 (1.00, 1.36), 1.05 (0.90, 1.22), 1.09 (0.94, 1.25), and 1.27 (1.09, 1.49), respectively (P for linear trend = 0.005). No association was apparent for older women. Conclusion We observed no association between chocolate intake and risk of CHD, stroke, or both combined in participants free of pre-existing major chronic disease. The relation for both combined was modified by age, with a significant positive linear trend and an increased risk in the highest quintile of chocolate consumption among women age <65 y. This trial was registered at clinicaltrials.gov as NCT03453073.