Two miles south of Shillingstone along the North Dorset Trailway is Gain's Cross. The stretch of the trailway between Gain's Cross and Stourpaine, has been recently opened in November 2010. A new bridleway bridge has been constructed over the River Stour at Enford, on the site of the old railway bridge, which was demolished in the 1960's. This new section means that there is a seven mile off-road link for cyclists, horse riders and walkers from Sturminster Newton in the north, through Shillingstone, down to Stourpaine in the south. This part of the trailway runs down the Stour Valley, and has links to The Stour Valley Way and Wessex Ridgeway long distance routes. The North Dorset Trailway, is part of a scheme to provide a cycle path/bridleway, from Poole, in the south, through Dorset and into Somerset, following the route of the former Somerset and Dorset Railway line.

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