events – Trail Fun

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Our Events 2026

Here is an overview of all TrailFun events for 2026.
Please note that the event dates are fixed, but the host farms may change.

Jan

10 Saturday, 10. January 26

Simonsig Wine Estate

TrailFun Summer Series 1 of 4

Simonsig Wine Estate is synonymous with the history of the South African wine industry, the Stellenbosch wine region, and the Malan family name.

Jan

24 Saturday, 24. January 26

Bellevue

TrailFun Summer Series 2 of 4

An iconic wine estate offering an exciting range of experiences which include tasting award-winning wines, casual dining, kids play areas and private venues. A destination with a revered position in South African wine history, Bellevue’s vineyard produced the world’s first commercially bottled Pinotage.

Feb

7 Saturday, 7. February 26

Middelvlei

TrailFun Summer Series 3 of 4

Middelvlei Estate, known for its hospitality and special farm atmosphere, offers a personal, unforgettable and authentic Stellenbosch Winelands experience for the whole family. By producing superb quality wines, brothers Tinnie and Ben Momberg are continuing the family’s legacy of winemaking that has lasted for over 100 years.

Feb

21 Saturday, 21. February 26

Kanu

TrailFun Summer Series 4 of 4

Founded in 1692 as part of the famous Nooitgedacht farm, Kanu underwent various changes and an accumulation of history to become what it is today. As of 1997, the land and the wines became known as Kanu.

Mar

07 Saturday, 07. March 26

Neethlingshof

TrailFun Autumn Series 1 of 4

Neethlingshof Estate has a long and rich tradition of wine making in Stellenbosch, the second oldest and most premier wine producing area of South Africa. The Estate occupies an incredibly privileged site with ideal natural conditions, soils, slopes, altitudes and climate to produce a variety of great wines.

Mar

21 Saturday, 21. March 26

Devonbosch

TrailFun Holiday Series 1 of 5

Imagine a destination sculpted around adventure’s principles, beckoning you to disconnect and hit play, where choices meet opportunities and opportunities unfold into adventures. Trade the hustle of modern life, screens, and notifications for the tranquillity of nature. Here, dirt and expertise, water and velocity reign supreme.

Apr

11 Saturday, 11. April 26

Kaapzicht

TrailFun Autumn Series 2 of 4

Kaapzicht is a 4th generation family farm – owned and run by the Steytler family who has farmed here since 1946. Wine is our passion, our livelihood and our life. We enjoy living in harmony not only within our own family, but also with our surrounding: our farm community, the multiple cultures around us and also with nature.

Apr

27 Monday, 27. April 26

Vredenheim

TrailFun Holiday Series 2 of 5

Vredenheim is approximately 331 years old and one of the oldest wine estates in the Stellenbosch area of the Cape Winelands. Owners Coen and Rikie Bezuidenhout acquired Vredenheim in 1986, after moving to the Cape from their game farm in Kwazulu Natal. The couple’s love for game explains the impressive variety of wildlife on the farm today, including blue wildebeest, springbok, eland, fallow deer and zebras. Vredenheim is now owned by the couple’s children, Basie and Elzabé Bezuidenhout.

May

9 Saturday, 09. May 26

Mooisplaas

TrailFun Autumn Series 3 of 4

Mooiplaas Wine Estate and Private Nature Reserve boast a pristine natural beauty. Owned and managed by Tielman and Louis Roos, the Mooiplaas vineyards lie on steep slopes of ancient mineral rich soils in the Bottelary Hills of Stellenbosch, overlooking Cape Town.

Jun

17 Tuesday, 17. June 26

Middelvlei

TrailFun Holiday Series 3 of 5

Aug

10 Monday, 10. August 26

Neethlingshof

TrailFun Holiday Series 4 of 5

Sep

24 Thursday, 24. September 26

Simonsig

TrailFun Holiday Series 5 of 5

Simonsig Wine Estate is synonymous with the history of the South African wine industry, the Stellenbosch wine region, and the Malan family name. These elements are intertwined in this family-owned farm, where the late Frans Malan produced the first bottle of our much-loved Kaapse Vonkel, South Africaʼs first Méthode Cap Classique made in the classic bottle-fermented style. He is also honoured for co-founding the thriving Stellenbosch Wine Route, a first in its time.

Feb

21 More runs coming soon ...

TrailFun Series