The region, without good agricultural land, was only sparsely inhabited by the Acadians, although several settlements were established in present-day Shelburne County and the LaHave River valley.

When the British took control of the region in 1713, they initiated a program of importing colonists from continental Europe, known as the Foreign Protestants, mostly from Germany and Switzerland.

During the 20th century, the South Shore became the centre of Nova Scotia's fishing industry, as fishermen in small boats operated from numerous tiny villages dotted along the coast.

As in many parts of Nova Scotia, many South Shore fishing communities all but disappeared as residents moved to larger urban centres in search of new opportunities.

As more tourists came to appreciate the beauty and culture of the region, coastal land prices rose, small businesses catering to the industry sprouted up, and a vibrant art community took root.

The tourism industry is concentrated in the towns of Lunenburg, Chester, Mahone Bay, Liverpool, the five beaches surrounding Riverport, and the fishing community of Peggy's Cove.

Lunenburg, a UNESCO World Heritage Site and the host to several major music festivals and arts events, plus the Bluenose II, is generally considered to be the cultural capital of the South Shore, with Bridgewater its industrial centre.

For the segment of tourism focused on Acadian history and culture, the major initiative is associated with the "Evangeline Trail" which extends through the Annapolis Valley and into the Southern Nova Scotia region as far as Yarmouth.