Enrichment during the indoor rearing of pullets destined for free-range systems may optimize pullet development including increasing motivated natural behaviors (termed ‘positive behaviors’) including foraging, dust bathing and chick play. Hy-Line Brown® chicks (n = 1700) were floor-reared indoors across 16 weeks with three enrichment treatments (n = 3 pens/treatment): (1) standard control, (2) weekly novel objects—‘novelty’, (3) perching/navigation structures—‘structural’. At 16 weeks, pullets (n = 1386) were transferred to nine identical pens within rearing treatments with outdoor range access from 25 to 65 weeks. Video cameras recorded the pullet pens, adult indoor pens, and outside range. During rearing, observations of play behavior (running, frolicking, wing-flapping, sparring) in chicks at 2, 4 and 6 weeks (total of 432 thirty-second scans: 16 observations × 3 days × 9 pens) showed no overall effect of rearing treatment (p = 0.16). At 11 and 14 weeks only the ‘novelty’ hens were observed to increase their foraging across age (p = 0.009; dust bathing: p = 0.40) (total of 612 thirty-second scans per behavior: 17 observations × 2 days × 2 age points × 9 pens). Observations of adult hens at 26, 31, 41, 50, 60 and 64 weeks showed that the structural hens exhibited overall more dust bathing and foraging than the control hens (both p < 0.04) but both novelty and/or structural hens showed small increases depending on the behavior and location (total of 4104 scans per behavior: 17 observations × 2 days × 6 age points × 9 pens × 2 locations = 3672 + an additional 432 observations following daylight saving). Across age, adult hens differed in the degree of dust bathing performed inside or outside (both p ≤ 0.001) and foraging outside (p < 0.001) but not inside (p = 0.15). For litter-reared pullets, additional enrichments may result in some long-term increases in positive behaviors.