We evaluated the accuracy and precision of wearable activity trackers and a pedometer (ATPs) in estimating steps and sedentary time (ST) in free-living settings. Thirty-two healthy men and women (M ± SD: age = 32.3 ± 13.3 years; BMI = 24.4 ± 3.3 kg·m−2) were directly observed during three, 2-hour sessions on different days while wearing 10 devices and a biometric shirt. A validated direct observation (DO) system provided criterion measures for steps and ST. For steps, bias ranged from −753 steps/2-hrs (Fitbit Flex) to −57 steps/2-hrs (Polar Loop) and CIs ranged from [−1,144, −365] (Fitbit Flex) to [−291,175] (Polar Loop) steps/2-hrs. For all devices, step estimates were strongly correlated (r = 0.90 [Fitbit Flex] to r = 0.97 [New Lifestyles pedometer model 1000]) with DO counted steps. Estimates of ST were not accurate and were weakly correlated (r = −0.06 and r = 0.06 for Fitbit Flex and Fitbit One, respectively) with DO ST. Most ATPs were not accurate and varied in precision in estimating steps and ST in free-living settings. Implications from this study are that although point estimates of steps from ATPs are not accurate, ATPs’ ranking of step counts among individuals was high. However, the Fitbit Flex and Fitbit One are not recommended for estimating ST. This study advances our understanding of the performance of ATPs in estimating steps and ST in free-living settings, and significantly advances activity tracker and pedometer validation studies.