With a network of lakes, rivers and dramatic hills set between the Indian Ocean and the Outeniqua Mountains, Wilderness is a unique destination. Often overlooked in favour of the nearby and much larger George and Knysna/Plettenberg Bay on either side, it is a destination in its own right. So don’t just drive through… stop and explore, as we did.
We were very, very fortunate. We had social media maven and blogger, Rose Greyling Bilbrough, aka Travelbug Rose (@gotravelbug) as our guide. She’s also the energy behind Wilderness South Africa, which has become hugely successful with over 10,000 followers.

Yes, Rose is a very enthusiastic flyer, and no, I resisted her invitation to try it. Of course it gives her an unparalleled perspective of the area’s many attractions. It’s just one of many activities you can do. I think a tandem flight would be a good bet! Photo: Travelbug Rose @gotravelbug

The Kaaimans River mouth with its signature bridge. There are hopes for reviving the Outeniqua Choo-Tjoe, and this route is begging for a return of the old steam train or something like the Franschhoek Tram. Photo: Travelbug Rose @gotravelbug

Waking up in the morning: View from my bedroom at The Wilderness Hotel. This was the original homestead where Wilderness all started, and it’s within walking distance of the village’s pavement cafes, restaurants and the beach.
On my first morning, Rose took me canoeing on the Kaaimans River. That’s the river one crosses just before entering Wilderness from the Cape Town side.
How many times have I just driven past this… intrigued by the houses alongside the river tucked into the steep slopes behind them!
It was just a short paddle to a spectacular waterfall, almost completely surrounded by steep, rock cliffs. A very, very special place.
Thank you Chris Leggat at Eden Adventures for the use of your canoe!
The rest of the day we explored Timberlake Farm Village — well worth a visit, and do stop at Pause Coffee Roastery. Wessel Kruger is serious about his coffees and you won’t be disappointed. The cheesecake was memorable too!
We drove into the farming area between Wilderness and the Outeniqua mountains and along a section of the old 75km Seven Passes Road. This was the original route between George and Knysna before the N2 opened. It was built between 1868 and 1883 by Thomas Bain and crosses seven rivers – the Swart, Kaaimans, Silver, Touw, Hoëkraal, Karatara and Goukamma – passing through indigenous forests and river gorges.
We stopped for tea and a snack at Hoekwil Country Cafe — “an unpretentious country secret on top of the mountain”.
Wilderness is a class act. The Milkwood Centre in the village is an absolute delight hidden behind the Spar and a fuel service station. The area has enough resident money to support pavement cafes, pubs and restaurants which were lively and well supported, even on Monday and Tuesday evenings. Pomodoro had a great vibe and served one of the best pizzas I’ve had.
I was intrigued that Wilderness had managed to retain its village feel and a sense of authenticity. It has so many attractions but hasn’t gone the way of George, Knysna or Plettenberg Bay. (In Franschhoek, I discovered How Franschhoek became such a successful tourist town after asking similar questions.)
I discovered that one of my former prep school teachers — “Masters” we called them then — lives in Wilderness, so I asked Hugo Leggatt if he knew the reasons. Here’s his reply:
“I’ve given thought to your question about the village feel of Wilderness. There are naturally various contributory factors but I think I could reasonably cull to two.
“In no particular order, the one is that there was no coastal road between George and Knysna until about 1950, when this section of the N2 was completed. The first proper road between the two towns was built by Thomas Bain in the years from c.1868. This was still the road when I first came here in 1947 and is the one now known as the 7 Passes route.
“So one can say that until 1950 one came TO the Wilderness, not THROUGH. Which meant that most houses were owned by retirees or were holiday homes.
“The second factor has to do with the ownership of the land. The property was owned, and named, by George Bennett (English) and his wife Henrietta ( a George girl) who built the initial homestead and ran it as a farm in the years on either side of 1880. After the Anglo-Boer War the property was sold to Montagu White (who had been Paul Kruger’s Consul in London in the years leading up to the war). Montagu lived at Fancourt but had The Wilderness run as a guest house/farm. He had some plots laid out but does not appear to have made any serious attempt to sell them.
“After Monty’s death in 1916 by mushroom poisoning at his Fancourt home, The Wilderness was sold to a new company The Wilderness (1921) Ltd. The main driving force behind this company was Owen Grant (1883-1964) who virtually ran the place for over 30 years. There were strict building regulations – no wooden or prefab houses, for example. Perhaps more importantly for your enquiry, all business was in the hands of the company – the hotel, the garage, the shop – and no guest houses were allowed.
“There is more detail, of course, but the net result was that practically the whole place was “residential”, with such commercial development as there was being controlled by Wilderness (1921). Things have changed with time but I think those two factors were major contributors to the village feel.
Wilderness is worth another, longer visit. If the beach, hang gliding (single or taken up in tandem by an expert), abseiling, canoeing, quaint shops and crafts, isn’t enough for you, then the walks and hikes will spoil you. Have a look at some of the Walks & Hikes in the area.
Thank you Rose for a great introduction! And for this video!