Western Cape
Trail Running Calendar Western Cape 2026-2027
Explore the best trail runs in province Western Cape for 2026-2027! Our updated list features 52 exciting trail runs across the region. Find your next trail run in province Western Cape below and join the trail community at these great events!
November 2026
A 12-hour trail challenge at Herold Wines where individuals and teams complete as many 5 km laps as possible on a marked mountain loop.
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.
A community fundraiser trail event at Lategansvlei offering 21 km, 14 km and 5 km routes with prize money and routes open only on race day.
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 run on Oak Valley Estate with 15 km and 25 km routes on single track, strong climbs, views of the Groenland mountains, GPX routes and sustainability focus.
A mixed MTB, e‑bike and trail run event in Koue Bokkeveld with multiple distances, water points, finisher medals and prizes for top finishers.
A 5 km uphill vertical kilometer at Eden Forest with about 1000 m ascent, self-sufficient entry requirements, compulsory gear, and a two-hour uphill cutoff.
A morning trail run at Morgenhof Wine Estate featuring scenic singletrack, two race distances and optional chip timing with medals and on-route refreshments.
December 2026
Experience rugged granite trails and fynbos slopes at Paarl Mountain with distances ranging from a family friendly 5km to a challenging 100km overnight ultra marathon.
Experience the scenic trails of Benguela Cove Lagoon Wine Estate with 5km and 10km routes featuring professional timing and a vibrant post run atmosphere in the Western Cape.
Test your speed at Klein Joostenberg Farm with a 3km obstacle course race or a high intensity 100m sprint through various physical challenges.
A mountain backyard ultra at Jamaka Organic Farm: repeat 7.8 km loops with 430 m ascent, shared camping, aid support, and a portion of fees donated to Sustainable Ceder.
Celebrate the festive season with a variety of mountain bike and trail running distances at Misty Valley Farm in the scenic Mossel Bay area.
Run through the scenic streets of Plettenberg Bay in a 5km or 10km road race supporting children with disabilities through the Sabrina Love Foundation.
January 2027
Trail runs of 5 km, 12 km and 18 km at Herold Wine Farm near Cradock Peak, limited to 200 entries with picnic meal options and race-day amenities.