Context: The onset of menopause has been associated with an increase in cardiovascular risk factors. However, little information is available about the rapidity of the menopausal transition and its relationship to the development of preclinical cardiovascular disease (CVD). Objective: Our objective was to assess whether the rate of carotid intima-media thickness (cIMT) progression over time differs according to 1) menopausal status and 2) rapidity of the menopausal transition. Design: We evaluated 203 community-based women aged 45–60 yr without previously diagnosed CVD who underwent three repeated measurements of cIMT as a measure of preclinical CVD over 3 yr. Menopausal status was ascertained at each visit based on menstrual cycle parameters and reproductive hormone profiles. Of these, 21 remained premenopausal, 51 transitioned, and 131 were postmenopausal throughout the observation period. Results: Age-adjusted cIMT progression rates were similar among premenopausal, transitioning, and postmenopausal women. In the 51 transitioning women, age was not related to rate of cIMT progression. However, the rapidity of menopausal transition was related to cIMT progression: women transitioning from pre- to postmenopause within the 3-yr period had a higher rate of cIMT progression compared with women with a slower transition. Statistical adjustments for the significant covariates of systolic blood pressure, body mass index, race, cigarette smoking, or hormone therapy use did not alter the findings. Conclusions: Among healthy women undergoing repeated cIMT measurement, a more rapid menopausal transition was associated with a higher rate of preclinical CVD progression measured by cIMT. Further work is needed to explore potential mechanisms of this effect.