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Trail Running Calendar near Wellington 2026-2027

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Explore the top trail runs near Wellington for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
10
Mo

Run The Vines

Trail Run 3 km 5 km 10 km 17 km
Trail event at Fairview Wine & Cheese on 10 August 2026 with timed 17, 10, 5 and 3 km family friendly distances, Paarl Trails fee and finisher medals.
Aug
22
Sa

Run The Vines

Trail Run 3 km 5 km 10 km 17 km
Run The Vines RTV 2026 #9 at Kloovenburg Wine and Olive Estate on 22 August 2026 offers 17 km, 10 km, 5 km and family 3 km options with on-farm trail routes.
Aug
29
Sa

Titan OCR

Obstacle Run 5 km 10 km
An obstacle course run near Klapmuts offering 5 km and 10 km trail courses with Elite and Fun categories, on-site medical support, food vendors and team entries.
September 2026
Sep
5
Sa

Run The Vines

Trail Run 5 km 10 km 17 km
Trail runs at Windmeul Kelder in Paarl combine farm routes with the Waterblommetjie Festival, local market stalls and a waterblommetjies and wine pairing session.
Sep
19
Sa

Run The Vines

Trail Run 3 km 5 km 10 km 17 km
Trail runs at Slanghoek Cellar with 3 km kids options plus 5 km, 10 km and 17 km distances, chip timing and finisher medals.
Sep
26
Sa

Titan OCR

Obstacle Run 5 km
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.
October 2026
Oct
3
Sa

The Pink Xtreme

Trail Run Walk 5 km 10 km Half Marathon
Trail run and festival at Rhebokskloof Estate on 3 October 2026 supporting CANSA, featuring 21km, 10km and 5km options plus a corporate team challenge.
Oct
10
Sa

Fairview Goat Run

Trail Run Walk 5 km 8 km 15 km 28 km
Charity trail event at Fairview Wine Estate in Paarl offering multiple trail distances, a wheelchair-friendly 5km class, beneficiaries, and event-day food and wine.
Oct
31
Sa

Run The Vines

Trail Run 3 km 5 km 10 km 17 km
November 2026
Nov
7
Sa

Winelands 10s

Trail Run 5 km 10 km Half Marathon
Trail running in Paarl with 21 km, 10 km and 5 km options, combined with festival passes and a beverage included.
Nov
21
Sa

Run The Vines

Trail Run 3 km 5 km 10 km 17 km
Trail running at Jason's Hill winery on 21 November 2026 with timed 17 km, 10 km, 5 km and kid-friendly 3 km options plus on-site wine and vendors.
Nov
28
Sa

Titan OCR

Obstacle Run 5 km 10 km
An outdoor obstacle course at Cape Joy, Klapmuts offering 5 km and 10 km routes with Elite and Fun categories, on-site support, vendors, and team entries.
December 2026
Dec
4
Fr

The Rock Ultra

Trail Run Walk 5 km 12 km ... 44 km 100 km
A mountain trail running event on Paarl Mountain with routes from 5 km to an overnight 100 km ultra, centered at the Afrikaans Language Monument.
April 2027
Apr
2
Fr

Pass2Pass Ultra-Trail

Trail Run 14 km 25 km ... 63 km 100 km
Trail running at Doolhof Wine Estate, Bain's Kloof Pass, with races from 14 km to 100 km plus live timing, aid stations and a race village.
July 2027
Jul
10
Sa

Bastille Day Trail Run - Franschhoek

Trail Run 6 km 10 km ... 25 km 35 km
Trail running at Plaisir Wine Estate in Franschhoek on 10 July 2027, offering distances from 6 km to 35 km with marked trails and on-course support.
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