Stellenbosch
Trail Running Calendar near Stellenbosch 2026-2027
Explore the top trail runs near Stellenbosch for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A literary fun run at Dornier wine estate where runners and walkers use unique Afrikaans WAT words as race identifiers across 10 km, 5 km and a 100 m sprint.
A complimentary trail event at Mitre's Edge offering Relaxed Run or mass-start race formats across multiple distances, free for qualifying Series entrants and HERO members.
A morning social trail run at Jonkershoek Nature Reserve supporting Grassroot Soccer, with a one-hour route, sunglasses trials, a goodie bag, coffee and a lucky draw.
Orienteering at Helderberg Farm near Somerset West with three mapped courses, farm access, and a boerewors roll included; pre-entry required by 15 Oct.
A 6.8 km trail at Ayama Slent Farm with vineyard tastings every kilometre, an entry fee of R300, 300 places and medals for all finishers.
A non-competitive 5 km silent disco run through Bloemendal vineyards with glowing headphones, multiple pace groups, a kiddies 200 m dash, and an after-run Silent Disco.
Trail trail run through Bottelary Hills vineyards and Renosterveld with distances from 7 km to 36 km, relaxed and race start options, socks and finisher medal included.
A 5 km community run and walk at Anura Vineyards on 31 October 2026 to raise awareness and support services for people affected by dementia.
November 2026
Trail running event at Avontuur near Somerset West offering 5 km and 10 km routes, on-course water and timing, medals, medical support, and a post-run food and entertainment area.
Winelands 10s Plaasdraf is a trail running event in Paarl on 7 November 2026 offering 21 km, 10 km and 5 km distances with Weekend or Saturday festival pass options.
Timed trail event at Huis Horison in Stellenbosch offering 10 km, 5 km and a 3 km family trail with evening registration and on-site market stalls.
Mountain trail races around Cape Town from 16 km to 100 miles featuring technical routes across Table Mountain National Park and a 7 516 m vertical gain on the 100 mile course.
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.