TrailFun Holiday Series | Middelvlei | 2027

The TrailFun Youth Day Trail Run 2026 takes place on Tuesday, 16 June 2026, at Middelvlei Wine Estate on Flamingo Street in Stellenbosch, Western Cape. This public holiday trail run celebrates new beginnings, participation, and the courage to show up — whether it is your first trail event, your first run in a while, or your first step back after a break.

Designed to be welcoming and beginner-friendly, the event offers clearly marked, walk-friendly trails with support along the route. Participants can run, jog, or walk at their own pace, making it ideal for first-timers, families, social runners, and anyone looking for a relaxed and encouraging trail experience.

Distances & Format

• 5km – easy and relatively flat
• 10km – more challenging, but still entry-level
• 15km & 21km – available as relaxed run options only
• Walkers welcome on all routes

Start Options

The Race

• 10km start: 07h40
• 5km start: 08h00
• Podium prizes for 1st, 2nd, and 3rd in adult categories only

Relaxed Run

• Start any time between 07h00 and 09h30
• Walk or run with no pressure
• On-the-day entries close at 09h20

What’s Included

• Oversized Holiday Series Butterfly Medal
• Matching pair of THE Socks
• Bottle of spring water
• Complimentary wine tasting at the finish
• Runner-only wine purchase specials
• Water points and on-route support

Part of the TrailFun Holiday Series, this Youth Day event can also be entered on its own. With its scenic wine estate setting, inclusive atmosphere, and focus on simply beginning, the TrailFun Youth Day Trail Run is a perfect way to spend the public holiday outdoors.

Please note: dogs are not allowed at this event.