11. Jan 25

TrailFun Summer Series 1 of 4

Simonsig Wine Estate

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

25. Jan 25

TrailFun Summer Series 2 of 4

Middelvlei Wine Estate

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.

08. Feb 25

TrailFun Summer Series 3 of 4

Delheim Wine Estate

Delheim Wines stands as a testament to a legacy deeply rooted in nature, spanning over seven decades. The ethos of conservation and emphasizing sustainable farming practices in wine making has always existed on Delheim.

22. Feb 25

TrailFun Summer Series 4 of 4

Kaapzicht Wine Estate

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.

08. Mar 24

TrailFun Autumn Series 1 of 4

Kanu Wines

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.

08. Mar 25

TrailFun Autumn Series 1 of 4

Devonbosch

Each day at Devonbosch invites you to embrace adventure and immerse yourself in nature’s raw beauty. Whether hiking, biking, swimming, eFoiling, or trail running, our diverse adventure offerings cater to every taste.

05. Apr 25

TrailFun Autumn Series 2 of 4

Neethlingshof Wine Estate

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.

27. Apr 24

TrailFun Holiday Series 2 of 5

Vredenheim

Vredenheim Wine Farm in Stellenbosch is no ordinary wine farm! We are family-owned and have something for everyone.

10. May 25

TrailFun Autumn Series 3 of 4

Bellevue Wine Estate

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.

24. May 24

TrailFun Autumn Series 4 of 4

Mooiplaas Wine Estate

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.

09. Mar 24

TrailFun Autumn Series 1 of 4

Slaley Wine Estate

Located on the foothills of the Simonsberg Mountain, Slaley’s rolling terroir boasts an array of rich mountain soil, temperate climate and cooling ocean breeze enabling us to cultivate classically styled wines made to age.

21. Mar 24

TrailFun Holiday Series 1 of 5

The Purple Windmill

Relax to the splendid views of the vineyards and surrounding hills. Just a short drive from Stellenbosch takes you to a beautiful farm setting, where you will be greeted by Dunkin, Dixie, and Daisy – our resident donkeys, and even warmer greetings from our friendly staff.

11. May 24

TrailFun Autumn Series 3 of 4

Zevenwacht Wine Estate

Situated on the Stellenbosch Wine Route, Zevenwacht has viticultural roots which penetrate deep into the historic past of South Africa. While literally meaning Seven Expectations, the name Zevenwacht exemplifies the abundant delights which await visitors to the Farm.

15. Jun 24

TrailFun Holiday Series 3 of 5

Middelvlei Estate

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.

29. Jun 24

TrailFun Winter Series 2 of 4

Kaapzicht

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.

13. Jul 24

TrailFun Winter Series 3 of 4

Durbanville Hills

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.

27. Jul 24

TrailFun Winter Series 4 of 4

Nooitgedacht Estate

With its historic charm and Cape Dutch roots, Nooitgedacht Estate is fondly known as one of the best venues in the Stellenbosch area for weddings, events, a range of experiences and corporate events.

24. Aug 24

TrailFun Challenge

Fort Simon

The success story of the Fort Simon Wine Estate was a testament to the vision and passion of the Uys family, demonstrating that their dedication had resulted in remarkable wines.

14. Sep 24

TrailFun Spring Series 1 of 4

Darling Cellars

The cool and temperate West Coast climate lends itself to a variety of different micro- and meso-climates which, along with the different soil types, lead to unique grapes which we guide into even more unique wines.

05. Oct 24

TrailFun Special

Paternoster

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.

19. Oct 24

TrailFun Spring Series 2 of 4

Jordan Wine Estate

From the Jordan hillside vineyards, one has spectacular panoramic views of Table Mountain, False Bay and Stellenbosch. Gary and Kathy worked internationally for two years, refining their high-energy instincts with practical experience. They returned home to build a cellar in 1992.

23. Nov 24

TrailFun Spring Series 3 of 4

Mitre's Edge Wine Estate

Family-owned and managed boutique winery, Mitre’s Edge, is nestled at the foothills of the Simonsberg Mountain, between Paarl and Stellenbosch. It is in this beautiful setting that winemaker Lola Nicholls, assisted by husband Bernard, focuses on producing relatively smaller quantities of high-quality, award-winning wines.

07. Dec 24

TrailFun Christmas Run

Vredenheim

Vredenheim Wine Farm in Stellenbosch is no ordinary wine farm! We are family-owned and have something for everyone.

2025

More events coming soon ...
TrailFun arrange runs for you in a safe environment, on a well marked route, that is fun, so you can relax and enjoy your morning run. Find Fun Me-Time when you get together with special people and laugh, run, drink wine and talk.

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