Winterton was initially called Springfield when it was established in 1905. The main road through Winterton is still called Springfield Road.

Springfield was renamed Winterton after H.D. Winter who was minister of Agriculture and later of Native Affairs in the old Natal Government. His grandson, the well-known mountaineer of the 1950's, Martin Winter, still lives on his farm in the area. Martin Winter climbed virtually every peak between the Sentinel in the North and Giant's Castle in the South.

Winterton was a tiny village on the banks of The Tugela River with a railroad siding for the most part of 50 years. Today the main road is lined with shops, post office, petrol stations and a hotel. The town also has a primary school, country club, retirement home, museum and 6 churches. It also is the home of a wonderful caring community who all work together to uplift its residents and those who live in the surrounding district.

It is the gateway to all the hotels and resorts in the Central Drakensberg. The Drakensberg Boys Choir School is close by as is the Anglo-Boer War battle sites of Spioenkop and Vaal Krantz