Resilience looks different in every climate, but the need to reduce risk while creating long term value is universal. Through two contrasting case studies in dense urban and rural seasonal settings, this session explores how the SITES v2 rating system guides landscapes that withstand environmental stress while delivering ecological, social, and economic returns. Victoria Ward Park in Honolulu demonstrates how a former industrial site can become a culturally grounded, high performing public space. The session will examine the key design and investment decisions behind creating an accessible downtown park that is both visually compelling and ecologically restorative. Discussion will cover integrating 60 percent native planting, filtering rainfall on site to reduce flooding impacts to nearby harbors, improving soil health, lowering water demand, and supporting community health through shaded gathering areas and multi-use paths. Participants will also learn how operational strategies, including water efficient systems and electric maintenance equipment strengthen long term performance and reduce risk. In contrast, KOA Terramor Outdoor Resort in Bar Harbor explores resilience within a highly seasonal, climate exposed rural landscape. This case study addresses how to balance sustainability, accessibility, and business viability while designing for extreme weather and durability. Strategies include preserving forests and wetlands as natural buffers, reducing impervious surfaces, concentrating infrastructure, composting organic waste, and selecting low impact materials to improve stability and minimize operational strain. Participants will leave with practical insights into how SITES v2 can inform investment decisions, measure performance, and align climate adaptation with long term value. Together, these landmark projects are united by a shared commitment to generational accessibility, ensuring resilient landscapes remain welcoming and functional for decades to come.