The rapid development of computer technology and easy access to the Internet for information from anywhere worldwide has also demolished the physical boundaries between schools and the outside world. This chapter talks about how learning occurs at different sites and how modern digital technology, focusing on digital stories, can facilitate learning to go across and connect different sites. It discusses how digital storytelling projects facilitate learning to cross the school gates to involve families and connect different sites of learning. A key feature of sociocultural theory is that learning is through socialisation: that humans develop through social interaction. There are other research studies bearing the concept of funds of knowledge which investigate how important others in the family and community context affect children's learning. Children's cognitive development is an apprenticeshipit occurs through guided participation in social activity with companions who support and stretch children's understanding of and skill in using the tools of the culture.