Pecking is one of the most concerning poultry welfare issues in the layer houses, especially in the cage-free (CF) housing system. Pecking behavior may lead to severe feather pecking (SFP) and cannibalism when birds feel frustrated, stressed, and dominant over other birds. Since pecking is caused by multi-factorial problems (e.g., hormonal influence, environment, dietary composition, and genetic differences), it is very important to find optimal strategies for reducing pecking damage. The objective of this study was to evaluate the effects of pullet age and management practices on pecking behavior and to identify the optimal pecking mitigation strategy. Four climate-controlled rooms were used, each housing 200 Hy-Line W36 pullets, for a total of 800 pullets from 0 to 16 weeks of age (WOA). Pecking mitigation strategies were tested at different ages, including an isolated chamber (IC) at 14 WOA, an IC with lotion (water, aloe vera gel, tea tree oil, calendula, and methyl anthranilate), and a pecking block from 15 to 16 WOA. Data on severe feather pecking (SFP) and mortality were collected daily from 13 to 16 WOA during the pecking block, IC, and IC with lotion treatments and from 0 to 16 WOA for the entire pullet cycle of age treatment. Results show that the SFP significantly increased with the bird’s age (p < 0.01). The SFP started with 5 WOA. About 16% of birds were found with severe peck damages by 16 WOA. In this study, pecking blocks did not show a reduction in pecking order, possibly due to pecking at alarming rates. Isolating birds with SFP damages into the IC and applying lotion resulted in a significant decrease in SFP (p < 0.05) and cannibalism (p < 0.05). This study provides a reference for commercial CF egg producers to develop on-farm management strategies for mitigating pecking damage and cannibalism.