TrailFun Holiday Series

SEP
24
2026
A public holiday trail run at Simonsig Wine Estate with 5 to 21 km routes, commemorative socks, an oversized medal and on-route support in a walk-friendly setting.
Half Marathon 15 kilometers 10 kilometers 5 kilometers

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TrailFun Holiday Series 5 of 5 : Heritage Day

Thursday 24 September 2026 at Simonsig Wine Estate, Kromme Rhee Road, Stellenbosch, Western Cape.

The TrailFun Heritage Day Run is a public holiday trail run that focuses on connection and belonging. The event emphasises continuity and movement while recognising personal and communal stories. Routes are designed to be accessible and walk-friendly so multiple generations can share the same trail.

Distances are well marked and supported on route:

  • 5 km : easy, relatively flat
  • 10 km : more challenging, entry-level
  • 15 km : available as Relaxed Run only
  • 21 km : available as Relaxed Run only

Entries include a fully marked trail route, walk-friendly sections, on-route support and water points. Each entrant receives an oversized Butterfly medal and a commemorative pair of THE Socks. Additional inclusions are a bottle of spring water, a single complimentary wine tasting at the finish, and runner-only wine purchase specials. A pet nutrition partner will be present at the finish with goodie bags and guidance; dogs on leads are welcome.

Walkers are welcome on all routes. Podium prizes are offered for first, second and third places in adult categories. The event is part of the TrailFun Holiday Series but may be entered as a standalone run. The event lists a typical age range of 12 and above. Visit the organization's website for the most recent information.

Half Marathon
15 km
10 km
5 km

Events nearby

A 16 km linear coastal trail from De Hoek, Noordhoek Beach to Camel Rock Restaurant in Scarborough; runners must carry their own hydration and required safety kit.
Trail runs at Sandringham Farm with 5 km and 10 km routes through blue-gum forest, dams and a guava orchard, plus prizes and on-site food.
A two-day Women's Day trail run at Middelvlei Wine Estate offering 5, 10, 15 and 21 km routes with marked trails, support, an oversized medal and event socks.
Trail event at Fairview Wine & Cheese on 10 August 2026 with timed 17, 10, 5 and 3 km family friendly distances, Paarl Trails fee and finisher medals.
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