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 70 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!
September 2026
Trail running event at The Lawns at the Roundhouse in Camps Bay on 5 September 2026 with 40 km, 27 km and 15 km routes around Table Mountain.
Gravel bike routes from 28 km to 125 km, plus 12 km and 5 km trail runs and a toddler 2 km at Leeuwenboschfontein on 5 September 2026.
Trail run through Overberg farm roads at Eikebos campground near Caledon, featuring 18 km, 12 km and 5 km distances with canola fields in bloom.
Forest road and trail runs at Nelson Mandela University George Campus with 21.1 km, 10 km and 5 km options, on-course water, distance markers and age-category prizes.
Trail runs at Windmeul Kelder in Paarl combine farm routes with the Waterblommetjie Festival, local market stalls and a waterblommetjies and wine pairing session.
TrailFun Spring Series at Darling Cellars offers trail routes from 5 km to 21 km, wine-entry options and a green puzzle medal that forms a coaster after four events.
Trail run at Devonbosch, Cape Town with timed 5 km and 10 km routes, water stations, medals, medical support, and post-run coffee and food.
Trail runs at Slanghoek Cellar with 3 km kids options plus 5 km, 10 km and 17 km distances, chip timing and finisher medals.
A community MTB relay and trail run in Montagu with team boomerang loops, 5 km and 10 km trail options, medals, prizes and on-site food.
A fundraising trail run at De Grendel Wine Estate supporting the Rohan Bloom Foundation, with GPX routes for 6 km, 11 km and 18 km and amenities for entrants.
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.
Heritage Day runs and walks at Dornier Wines in Stellenbosch raising funds for children’s charities, with 5km, 10km, 20km and team relay options.
Multi day trail run near Boggoms Bay with two and three day options, daily coastal stages, village accommodation and meal packages.
A 5 km run or walk through the vineyards of Tenuta GioMaLi in Knysna with a goody bag, return taxi and proceeds supporting local charities.
Coastal trail run in Stilbaai with 16 km and 5 km routes, cash prizes for male and female categories and a community finish at Jagersbosch Community Care Centre.
A 5 km trail obstacle course at Kleine Hopefield on 26 September 2026 offering Elite timed competition and a noncompetitive Fun category, with team entry options.
A coastal trail event near Strandfontein with 21 km, 10 km and a 2 km kids run. Run West is a non profit focused on environmental awareness, community upliftment and education through NEST.
Trail routes from Waterford Estate in Stellenbosch follow the Blouklip River and vineyards, offering 8 km, 15 km and 24 km options with aid stations and compulsory kit on longer routes.
October 2026
A three day all inclusive trail running and walking experience in the Tulbagh Valley with glamping or guesthouse accommodation and local food and drinks included.
Hout Bay Twin Peaks on 3 October 2026 features 42 km, 30 km and 16 km trail routes from Dunes Restaurant that visit Noordhoek Peak and Karbonkelberg.