Leisure participation is associated with health benefits and withdrawal from leisure is a commonly associated outcome of cognitive decline. We investigated the feasibility of a web-based app ‘ArtOnTheBrain’ to promote involvement in enjoyable recreation in seniors with cognitive decline. ArtOnTheBrain employs artwork focused activities involving learning, solving puzzles, and socializing with storytelling and discussion. Iterative qualitative feedback interviews were undertaken to drive customizations of the app and establish user acceptability with two groups of 6 participants experiencing mild cognitive impairment, early dementia, and their family members. All participants became independent in navigating the app. Those experiencing cognitive decline commented it made them feel “smart” and their “opinion mattered”. Family valued opportunity for enjoyable interactions outside those concerning daily responsibilities. Technology can be leveraged to support engagement with complex recreation to improve well-being with future investigated secondary outcomes examining benefits in social networks, life space, cognition, and health service utilization.