He began encouraging members of his church's social guild to take "recreative and educational" holidays, rather than trips in "wakes week" to resorts such as Blackpool.

He continued his pastoral duties until 1897, when he and Paton set up the Co-operative Holidays Association (CHA), with the aim of providing "recreative and educational holidays by purchasing or renting and furnishing houses and rooms in selected centres, by catering in such houses for parties of members and guests and by securing helpers who will promote the intellectual and social interests of the party with which they are associated".

[1][2] His approach to encouraging working people to admire the natural world and develop themselves was influenced by Christian Socialism and by such figures as Matthew Arnold, John Ruskin, Henry Thoreau and William Morris.

Early speakers at CHA holidays included Hardwicke Rawnsley, and Leonard himself supported the Independent Labour Party and spoke at rallies with Keir Hardie.

After moving first to Whitby, then to Rhu on the Firth of Clyde, and then again to Hayfield in Derbyshire, he and his wife and daughter settled at Marple Bridge near Stockport in 1910.

[1][2] At the end of 1912, Leonard announced that he was stepping down from the CHA to found a new organisation, the Holiday Fellowship (HF), partly because he disapproved of the CHA General Committee approach that encouraged more middle class rather than working class clients to stay in the centres,[3] and partly because he wanted to develop the international relations side of the organisation.

Memorial plaques were set up on Cadair Ifan Goch at Maenan above the Conwy Valley opposite Dolgarrog and on Catbells near Keswick in the Lake District,[2] describing him as "the 'Father' of the Open-Air Movement in this Country", and bearing the epitaph: "Believing that 'the best things any mortal hath are those which every mortal shares' he endeavoured to promote 'joy in widest commonality spread'.