The steep sided valley in which Winterborne Stickland lies, gives the village its name:

Stickle - meaning 'steep' is still found in the Dorset dialect, and the reference is to the steep lane known as Chalky Path which climbs out of the village.

Winterborne - refers to the small stream that flows through the outskirts of the main part of the village, where the Primitive Methodist Church, Wesleyan Methodist Church, St. Mary's Church of England and the Shire Horse Inn are located.

Perhaps because of its isolation, Winterborne Stickland was for so long, self contained and residents rarely ventured as far as Blandford, four miles away, Winterborne Whitechurch, or the small village of Tolpuddle, which features in Australian history.

The oldest building is Quarleston Farm that dates back to the 15th Century in parts, and was owned by the Quarrel family.

Winterborne Stickland lies on the edge of the Milton Abbey estate and legend has it that a tunnel ran from the village to the Abbey, but nothing was ever found.

A village sign created by a group of local craftsmen stands in the centre of the village, showing in its various panels, all the features and activities of the village including the mill, smithy, well, agriculture, spinning and the making of Dorset buttons. The streets of the village are lined with thatched roof cottages and quaint single fronted dwellings. ⁶

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