Crowddreaming is an Erasmus + KA3 social inclusion project which aims to encourage awareness to both teachers and young people about the epochal challenge upon which the new generations are called upon, they will be among the first in history to find themselves passing down a digital cultural heritage. Crowddreaming raises awareness of this challenge and stimulates the adoption of the new paradigms of thought required to operate in the digital dimension. Based on a principle of content-based learning, each edition invites the participants to contribute to the construction of a digital monument, placing them on the challenge of generational transmission of digital cultural contents. The project will develop a curriculum which will be piloted in Europe. Trainers will be trained in the curriculum and will support teachers who will learn the course contents through MOOCs. The practice already took place in Italy as a competition in schools for four years already will be spread around Europe, namely through a pilot it in Italy, Greece, Latvia and Croatia. Students in the crowddreaming activity are invited to co-create a digital monuments which are imbedded using augmented reality technologies in a physical location of cultural value. Crowddreaming uses social technology as a tentative answer to several challenges in the Digital Age related to teaching and developing cultural heritage and heritage-related skills. The three big challenges addressed in the crowddreaming methodology are the Challenge of speed, form and persistence.