“Principles of Street Art,” an initiative promoted and organized by GoMad Concerti on 09/18/2021 as part of the European project INSIDES, provided for the realization of an art workshop aimed at teaching the basics of painting on canvas to two groups made up of young and old people, exploiting art as a creative key capable of destroying age stereotypes by activating a channel of connection between generations that are anagraphically distant from each other. The Workshop was led by a professional artist who first explained to the two groups the theoretical foundations useful for fully understanding the proposed art form, and then moved on to the practical phase of the project, which involved as many as 8 paintings on canvas by all participants. Art therapy allows elderly individuals to significantly reduce symptoms related to depression and memory loss, also proving to be an effective tool in counteracting the neuropsychological aging process and limiting complications at the functional level, typical of Alzheimer’s and other forms of dementia. The power of color makes it possible to recover sensations and memories of past life moments, experimenting with alternative methodologies that may prove more enjoyable and attractive. This type of initiative allows the elderly to create a new role for themselves, reinforcing their identity and self-esteem, through products and artifacts that restore a sense of control over reality and give new meaning to experiences. The workshop allowed young and old to come together and experience a common activity in a creative way, sharing an interactive experience by being a group and activating that important process called intergenerational support. It is important to emphasize that intergenerational support is an important resource not only for the more fragile individuals, who thanks to the younger people are able to sustain the autonomy of their active skills, but also for the younger individuals, who thanks to the closeness with a group of older people can learn a multiplicity of experiences useful for their own moral, educational and work growth.