The Greenway Initiative, proposed by Ontario Nature, endeavours to reconnect the province’s fragmented natural landscapes through a system of cores and corridors. Non-governmental organizations like Ontario Nature are leading the effort to conserve the province’s natural heritage through public-private incentive-based tools including conservation easements and stewardship agreements. The rationale to incent conservation through public-private partnerships is to overcome the politically- and financially- unfavourable consequences that limit the effectiveness of regulatory approaches to achieve conservation objectives at the local scale. However, public-private incentive-based conservation tools also generate trade-offs that maintain the need for traditional regulatory approaches. This paper argues that in addition to established public instruments, incentive-based conservation tools to promote stewardship on private land are necessary to achieve broader conservation objectives. With a combination of public, private and third sector approaches, an integrated set of strategies is recommended, in which planning choices and trade-offs are made clear.