Upland regions in the UK are increasingly under consideration as potential areas for the creation of woodlands. This is driven by a combination of factors, including the aims of UK forestry policy to increase woodland cover, changes in current upland land-use and management, agro-environment schemes in national and international policy and an increasing public awareness of the ecosystem service benefits landscapes can deliver for society. Creating new woodlands in upland areas is challenging, partly due to concerns of the potential impacts from a change in land use and also due to stakeholder perspectives. This research carries out a rapid TESSA ecosystem services assessment of a 250km2 grass dominated and sheep grazed Cumbrian (England) upland landscape and applies plausible alternative woodland creation scenarios of woodland cover percentages. The assessment focusses on changes these scenarios will deliver in terms of key ecosystem goods and services, which are identified by stakeholders to be of high importance to the study area. The results indicate that, under lower woodland percentage scenarios, no drawbacks and only benefits on all indicators are expected. However, a more complex outcome would be expected from the higher percentage woodland scenarios. The research furthermore adds a qualitative element to the overall understanding, by carrying out a Q-methodology investigation of stakeholder perspectives of upland woodland creation. The findings suggest that stakeholder perspectives are a powerful influence in upland woodland creation. The two components of research methods applied to the study complement each other and offer a greater understanding of this complex topic and identify barriers and opportunities for woodland creation in the uplands of Cumbria.