Trail Running calendar near Windsor 2026-2027

We have found 448 Trailruns within 80 miles of Windsor. See below where and when you can find the races.

Run laps through Denbies Wine Estate in the Fire Horse Run, a timed off road challenge on an undulating 5.3 km loop with distances from 5 km to ultra. Pick as many laps as you like within a seven hour window for a flexible, scenic race day.

A circular 46 miles route through Cambridgeshire visiting four former RAF Pathfinder Force airbases, starting and finishing at RAF Wyton. Entries open 1 Jan to 24 May; minimum age 18; entry includes a course booklet, t-shirt and medal.

A multi-distance running event in Bath that routes through two restored railway tunnels, including a 1672 m subterranean section. Distances range from a 500 m Colourburst to an ultramarathon, with the start and finish at Brickfields Park.

A multi-distance road and trail event around Ousden and Bury St Edmunds offering 5k, 10k, half, marathon and ultra options. Aid stations appear every 10k, parking is included and bespoke finisher medals are provided.

Tackle scenic, hilly trails at Wendover Woods with a half marathon, a 10k and a junior 1k on 7 June 2026. Enjoy forest scenery, a cafe and adventure playground plus medals, photos and prizes for top finishers.

Run Bournemouth's beach on 7 June 2026 from Bournemouth Pier, choosing a 5K or 10K across sand and groynes. A friendly, marshalled event that asks for respect and good sportsmanship.

Join the Coombe Hill Fell Race in Wendover for a punchy 7 km with about 220 m of climb, including a steep ascent and descent. On the day entry is available and your entry includes a pint at the finish.

Trail races at Alice Holt Forest in Surrey offering 10 km and half marathon routes with chip timing, feed stations and on site medical support. Finishers receive a medal, event merchandise, a snack and a drink.

Join Chase The Sun at Clapham Common on 10 June 2026 for a lively 5K or 10K loop around the park, passing the Bandstand and mostly on footpaths. Enjoy chip timing, a unique themed medal, free race photos and post race goodies.

An evening 10K trail race through Moors Valley Country Park in Ringwood as part of the Wildwood Trail Series. Single lap forest course with chip timing, aid stations and an eco friendly wooden finisher's medal; canicross option available.

Off-road 10 and 20 mile trail races around Fotheringhay, starting at Castle Farm Campsite. Routes run through fields, bluebell woodlands, riverside paths and old railway lines, with camping available and eco-friendly water stations.

A 100 mile non stop foot race along the full South Downs Way National Trail from near Winchester to Eastbourne with marked route, 12 aid stations, medical support and a 30 hour time limit.

A 50km non-stop trail race on 13 June 2026 along the South Downs Way from Matterley Bowl to Queen Elizabeth Country Park, featuring 4000 ft of climb, four aid stations, full medical cover and a 9 hour cut off.

A multi distance trail event in the Cotswolds on 13 and 14 June 2026. Based at Cirencester, it offers loop and staged 100 km options with regular rest stops, medical support, camping and finishers awards.

Scenic off road trail running around Bewl Water in Kent, with forest paths, open countryside and lake views. Choose 10km, Half Marathon, Marathon or 50km Ultra, starting and finishing at the Visitor Centre with chip timing and checkpoints.

Take on the YHA 14 mile trail run on 14 June 2026, starting with a climb and featuring slippery chalk descents and muddy puddles. GPX and maps available, water, tea and cake after the finish, limited parking so travel by train or bike.

Trail races at Watership Down feature marathon, half marathon and 10K single lap courses on mainly off road footpaths, reaching high points with county views. Events include chip timing, marshals, water stations and finishers medals.

Timed multi-distance event on a 5.3 km riverside loop in Walton on Thames with a 1.5 hour start window and a seven hour time limit, offering a finishers medal or a lower cost no medal entry.

A multi terrain 5 km race at Blackpit Farm near Silverstone featuring woodlands, lakeside lawns and farmland. Finishers receive a bespoke medal and free parking is available at Blackpit Brewery.

Community evening races at Robertsbridge Rec Ground offering 10k, 5k and a junior run on a multi terrain undulating course. Volunteer marshals, a BBQ, a post race bar, bespoke medals, trophies and free parking are available.