The objectives of the present study were to evaluate the effects of dry period length on ovarian activity in cows fed a lipogenic or a glucogenic diet within 100 days in milk (DIM) and to determine relationships between ovarian activity and energy balance and metabolic status in early lactation. Holstein-Friesian dairy cows (n = 167) were randomly assigned to one of three dry period lengths (0, 30, or 60 days) and one of two diets in early lactation (glucogenic or lipogenic diet) resulting in a 3 × 2 factorial design. Cows were monitored for body condition score, milk yield, dry matter intake, and energy balance from calving to week 8 postpartum, and blood was sampled weekly from 95 cows from calving to week 8 postpartum. Milk samples were collected three times a week until 100 DIM postpartum for determination of progesterone concentration. At least two succeeding milk samples with progesterone concentration of 2 ng/mL or greater were used to indicate the occurrence of luteal activity. Normal resumption of ovarian cyclicity was defined as the onset of luteal activity (OLA) occurring at 45 DIM or less, followed by regular ovarian cycles of 18 to 24 days in length. Within 100 DIM postpartum, cows with a 0-day dry period had greater incidence of normal resumption of ovarian cyclicity (53.2%; 25 out of 47 cows) compared with cows with a 60-day dry period (26.0%; 13 out of 50 cows, P = 0.02). Independent of dry period length or diet, cows with OLA at less than 21 DIM had a greater body condition score during weeks 1 and 2 (P = 0.01) and weeks 1 through 8 (P = 0.01) postpartum compared with cows with OLA at greater than 30 DIM. Cows with the first ovarian cycle of medium length (18–24 days) had greater energy balance (P = 0.03), plasma concentrations of insulin (P = 0.03), glucose (P = 0.04), and insulin-like growth factor I (P = 0.04) than cows with long ovarian cycle lengths (>24 days) but had lower plasma ß-hydroxybutyrate (P <0.01) and liver triacylglycerol (P = 0.02) concentrations than cows with short ovarian cycle lengths (24 days) ovarian cycles during the first ovarian cycle postpartum were associated with severe negative energy balance and poor metabolic status in early lactation.