Oswestry
Trail Running Calendar near Oswestry 2026-2027
Explore the top trail runs near Oswestry for 2026-2027! We've gathered 59 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A WFRA registered Winter Series fell race near Little Stretton covering 8.1 km with 762 m ascent, four steep climbs, mandatory kit, pre-entry or limited on-day entry.
Community Santa run at Montgomery School with 1 and 3 mile routes, optional Christmas dress, on-site refreshments and free parking; children under 14 must be accompanied.
Around 9 miles of multi terrain trails near Bishop's Castle with about 1700 ft ascent, chip timing, marked route and some dog friendly sections.
A trail half marathon at Loggerheads Country Park with solo and teams of three relay options, varied terrain and feed stations each 7 km lap.
A 39th annual timed footrace between Little Stretton and Stiperstones covering about 9 or 10 miles, open to solo runners and declared pairs with on the day registration.
December 2026
6.4 km trail race at Llandegla Forest on 4 December 2026 with 229 m climb; compulsory headtorch and kit, and a safety briefing before racing.
Winter endurance on The Wrekin: cover 160 miles and 47,000 ft of ascent in 48 hours; entry requires prior 100 mile experience and places are limited.
A 9 mile fell race near Cardington on 6 December 2026 with about 2,600 ft of ascent, online entry only, limited to the first 180 entrants and over 19s.
Night trail race in Llangollen covering about 8 km with 244 m ascent; partially marked route, head torch required and minimum age 16, entry fee £5.
A 24 hour out and back trail challenge from Llanbenwch Caravan Park with 98 km, 70 km and 50 km options for solo entrants or teams.
A festive trail race at Bwlch Penbarras with a mystery course of 6 to 12 kilometres, a canicross category, marshals and a mince pie at the finish.
A Boxing Day 5K up and back at Stiperstones to the Devil's Chair featuring mixed terrain, online entry opens 1 November and official times for registered entrants.
A multi-distance running event at Shrewsbury Sports Village where runners cover as much distance as they can between sunrise and sunset. Options include 5K, 10K, half marathon, marathon and ultramarathon with lap cards used to record distance.
Short downhill fell race from Moel Famau to Cilcain, about 4 km with 350 m descent, provisionally set for 27 Dec 2026 and for participants over 16.
January 2027
A scenic 5k loop from the Caravan Park and Cafe at Llanbenwch near Ruthin, featuring mixed road and trail surfaces, electronic timing and a finisher medal.
The Holly Challenge on 23 January 2027 offers 5K, 10K, half marathon and marathon on the lanes of Lightmoor Nature Reserve near Telford. Entries are limited to 50 places and all finishers receive a medal.
February 2027
Trail races at Carding Mill Valley, Church Stretton with 10K, half and full marathon options across The Long Mynd and National Trust land.
A 17.7 km fell race in Carding Mill Valley with about 1300 m of ascent, held on Sunday 7 February 2027, offering pre-entry and entry on day options.