In the juncture of virtual and physical learning environments, Experience Sharing Community (ESC) supports learners to create course related posts based on their experience in physical environments, share posts in virtual environments, and interact with peers and instructors. The ESC, via technology and instruction designs, provides students with a place to create, interact, and reflect, influencing diverse learning experience. The idea of ESC is not brand new, similar topics of ESC were explored by studies related to social media use in education for two decades. While there is still a lack of a systematic understanding of how technology and instruction together contribute to learner behavior and experience. This dissertation mainly includes two projects. Study#1 investigates creating an ESC via Instagram in an online learning environment during the Covid-19 pandemic. In a large online course, Introduction to Environmental Psychology, 110 voluntary participants posted photos of their surroundings that were related to the course on Instagram every week. Mixed methods including survey experiment, interview and network analysis were applied to understand their behavior and experience in this community, and how key features of Instagram influenced their experience. The main environments’ features to afford interaction, behaviors including interact, post, and reflect, experience including social presence, cognitive presence, sense of place and sense of belonging, and the relationship between environments, behaviors and experience were identified and explored. While social media such as Instagram was an effective tool for building the ESC, they were not designed for educational settings, and many of their features had to be adapted to better support the ESC. After summarizing the lessons learned from Study#1, I designed and developed my own web application to provide a more tailored experience for students. In Study#2, 114 voluntary participants followed the similar instruction as Study#1 and posted photos on the new app in the same course in a traditional learning setting after the pandemic. This project received positive feedback in terms of engagement, sense of place, and knowledge understanding. Mixed methods including design-based research, interview, and log analysis were applied to further understand how both technology and instruction design influenced student behavior and experience in this community. Based on these two projects, I summarized a framework of conducting longitudinal study to understand participant experience using web applications, regarding its research design and technology needs. This summary extends the scope of the dissertation beyond the ESC, to inspire research methodology development such as Ecological Momentary Assessment. Overall, this dissertation is a unique and valuable addition to the educational landscape, on “what is ESC” and “how to create ESC”, providing students with an opportunity to engage with their peers and expand their knowledge in a dynamic and interactive way. The project also highlights the potential of technology to support and enhance traditional classroom settings, demonstrating the power of innovation and creativity in the pursuit of educational excellence. This learning community can be expanded to broader class settings in the future, including across classes in design fields such as Human-Centered Design, Architecture, and Landscape Architecture. Students across different disciplines can benefit from sharing their knowledge and experience in the community. In addition, the open-sourced technology framework of longitudinal study via web applications including study design, data collection, data analysis and presentation for stakeholders of researchers and instructors can facilitate the research innovation beyond educational technology field.