After 1700 the settlers attracted to the remote corners of the Overberg and began searching for new land to farm. It had to have an ample supply of water and the soil had to be fertile.
The pathways and tracks through Tradouw (Tradouw is a Hottentot word meaning "the women's poort or footpath") Poort proved to steep for them to be turned into wagon routes and the journey via Cogman's Kloof was both tedious and time consuming for those wishing to sell their produce in Swellendam. In 1867 plans were made for the construction of a road, to be built by convicts, through the Langeberg linking Swellendam and what is now the village of Barrydale.
In time the farmers who settled on the lands in the valley at the top of the Tradouw Pass decided they wanted their own church and the chosen spot was at the point where the R62 and R324 meet. Thus the village owes its existence to both a church and crossroads.
The village was named after James Barry, an early settler in the Overberg, who was not only a trader but acted as lawyer, agent and auctioneer, deputy sheriff and commandant of militia. In the early days of Barrydale there was a little in the village apart from nagmaal houses used by the farmers coming to the village to attend church. However, there was a school.
After the collapse of the "Barrydale Empire", William Sterner, who arrived as a "smous" (trader), became Barrydale's financial success story owning the general dealer shop, the hotel, the draper's, the shoemaker's and the gunsmith's. Barrydale grew over the years and by 1921 the Municipality was established. The Barrydale Cooperative Winery and Distillery was formed in 1940 and wine produce is still sent there today where choice wines such as Chardonnay, Sauvignon Blanc, Merlot, Cabernet Sauvignon and Cabernet Franc are bottled. Visitors are welcome to enjoy tasting, cellar tours and purchase wine.
The climate here is especially kind to winemakers, fruit growers who deliver to export markets and visitors who drive up or scale the scenic Tradouw Pass to admire the fynbos, dramatic rock formations and abundant birdlife. There are many sign-posted hikes like the Bertus Cooke Trail or the Moerasrivier Trail (maps available at Tourism Bureau).
Barrydale offers farm tours, horse riding, 4x4, trout fishing, a great biker's stopover on Route 62, plenty lovely restaurants, pubs and farm stalls, biltong shops and a wide range of accommodation. The Heritage Garden represents the region's floral and succulent kingdom; each of the 8 beds gives a true reflection of the different groupings of plants in their natural habitat. Just outside of Barrydale you will also find the Warmwaterberg Hot Springs, Ronnie's Sex Shop and Sanbona Wildlife Game Reserve.
(from Overberg Online)