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Trail Running Calendar near Stellenbosch 2026-2027

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Explore the top trail runs near Stellenbosch for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
Club orienteering in Simonstown on 14 November 2026 with three mapped courses (4.2 km, 3.4 km, 2.5 km) meeting at SA Navy Parking.
A multi-distance trail race series in Cape Town featuring routes across Table Mountain National Park and the Cape Peninsula with significant elevation gain.
A trail running event at Jason's Hill Winery with multiple distances including kids categories, timed entries by BoutTime, on-farm routes, waterpoints and finisher medals.
Join the final Spring Series trail run at Blaauwklippen Wine Estate featuring distances from 5 km to 21 km and unique collectible puzzle medals.
A 6 km off-road run at Neethlingshof with five wine-tasting stops, a bottle of wine included, on-site food and entertainment, and prizes for best dressed.
Outdoor obstacle race at Cape Joy near Stellenbosch with 5 km and 10 km options, Elite and Fun categories, on-site medical support and event facilities.
Trail runs of 25 km, 15 km and 5 km through Oak Valley Estate with rugged single track, elevation gain, a sustainability focus, finisher medal and a bottle of Oak Valley wine.
A community-led morning at Sandy Bay with running and walking options on coastal and mountain trails, including 10 km, 5 km and a 3 km family walk.
A 5 km uphill Vertical Kilometer in Eden Forest with 1000 m climb, limited entries, compulsory kit and a two hour uphill cutoff.
A scenic trail run at Morgenhof Wine Estate offering 7 km and 11 km singletrack through Winelands slopes, optional timing and refreshments with medals for finishers.
December 2026
Trail running on Paarl Mountain with marked routes from 5 km to a 100 km overnight ultra and a race village at the Taal Monument.
A weekend of trail running and mountain biking on singletrack at Muratie Wine Estate, featuring 42 km MTB and 21 km trail run options and fundraising for trail maintenance.
April 2027
Three trail distances on the Simonsberg from Plaisir Wine Estate, with restored singletrack, water points, podium prizes and proceeds supporting river conservation.
June 2027
Trail races on Table Mountain offering 50 km, 30 km and 16 km courses with significant elevation, refuel stations and mandatory safety kit.
July 2027
A multi-distance trail event at Plaisir Wine Estate on 10 July 2027 with marked routes, aid stations, race timing, finishers medals, and early-entry apparel rewards.
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