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Background and Objectives Two exploratory 6-month pilots of triadic walking with culturally celebratory social reminiscence in gentrifying neighborhoods tested feasibility and health impact among normal and mildly cognitively impaired (MCI) older Black adults. Research Design and Methods Fourteen triads walked 1-mile 3×/week, using a navigational application with image-based reminiscence prompts. Focus groups evaluated perceived health impact and experience. Primary outcome measures were program evaluations (feasibility), pre–post self-report health, Montreal Cognitive Assessment, blood pressure, and weight. Analysis used mean rank scores for program evaluations, pre–post paired t -tests for health outcomes, and thematic coding for 30 focus groups. Results Feasibility: Retention was 74% and 86% for pilots, and 100% and 92%, respectively, were "extremely likely" to recommend to friends/family. Mean rank scores indicated appropriate pace and dose, effective conversational prompts, and program readiness with minor changes. Health impact: Self-rated health, mood, activity levels, and energy improved, days feeling downhearted decreased, and days feeling calm/peaceful were maintained or improved. Among Cohort 2, cognitive assessment scores were maintained or improved for 67%; for MCI, 76% had mean improvement of 2.4 (p  = .045). Blood pressure and weight decreased for 78% and 44%, respectively. Focus groups: Perceived impact of triadic walking included increased physical and social activity outside the program, increased awareness of cognitive decline risk and personal agency, and deep-seated sense of community connection. Discussion and Implications Triadic walking provides structure, accountability, connection, and purpose, motivating sustained engagement. Walking programs that center socialization, particularly within culturally meaningful contexts, may be more effective among older Black adults. Clinical Trial Registration Number NCT05906654 ; NCT05906667 [ABSTRACT FROM AUTHOR]