ABSTRACT Objectives Postgraduate programs that use ‘bootcamps’ to help trainees transition into new clinical roles usually solely target entry to residency, failing to address other critical transition periods. We developed, implemented, and evaluated a resident-led transition-specific bootcamp curriculum in our Pediatrics program and described our first 3 years of experience. Methods Our bootcamp curriculum was developed around Kern’s framework. A needs assessment identified key transition periods (Incoming Resident [IR]; Night Float [NF]; Ward Senior [WS]). Teaching content and methods were informed by Residents-As-Teacher principles. Program evaluation included surveys exploring trainees’ satisfaction, and perceived knowledge and self-efficacy before and after bootcamp participation. For the IR bootcamp, knowledge and behaviour were objectively assessed through written examinations and Observed Structured Clinical Examinations (OSCEs). Results Twenty-seven pediatric residents participated in the IR bootcamp, 26 in the NF bootcamp, and 25 in the WS bootcamp. Trainees’ baseline self-reported knowledge and confidence around clinical skills taught showed an improving trend post-bootcamp in all transition periods. Strengths identified included the level-appropriate teaching content and residents’ engagement as teachers. Conclusions Bootcamps can help residents adapt to new roles and should target all key transitions within the training continuum. Capitalizing on resident leadership for bootcamp curriculum development and implementation is instrumental to its success.