This is a reflective paper that concerns the role of higher education in enhancing social entrepreneurship, as it is implemented in the context of Dorset, UK and Avalon, Canada. The cases of two universities, Bournemouth University in the UK and Memorial University of Newfoundland in Canada are used in order to mirror approaches with which higher education can enhance and enrich social entrepreneurship. Social entrepreneurship in this paper is identified as a notion of emphasising the "social" that is linked with commerciality in resolving societal issues. By utilising theoretical dimensions of social entrepreneurship the paper develops a framework in an attempt to interpret the context of the cases under consideration. In so doing, it uses the notion of entrepreneurial orientation. Some of the questions the paper addresses are concerned with the commercially orientated, social welfare or mixing-the-two markets that universities in general serve regarding social entrepreneurship and, more specifically the role of Bournemouth University and Memorial University of Newfoundland respectively as drivers that may support social enterprises to maintain their value base. It also discusses the differences between the two chosen regional contexts i.e. the focus on the third sector entrepreneurship in Dorset, UK in contrast to the market-oriented entrepreneurship in Avalon, Canada. Finally, the degree of participation by the university students and members of staff is examined. Methodology-wise the paper is based upon primary research of qualitative nature via conducting of semi-structured interviews with university students and members of staff. Additionally, collection of secondary data is used. In summarising its findings, the paper argues that the role higher education can play for social entrepreneurship in both cases is highly regarded, however there are a number of hurdles that have to be overcome. Ultimately, they are these findings that create a base for planning research on social entrepreneurship in the future by looking at cases outside the university web.