Trail Running calendar near Windsor 2025-2026

Run Upcote Spring Trail is a limited entry 5 mile off road route around Upcote Farm near Cheltenham, featuring forest tracks, climbs and scenic Cotswolds views. Expect chip timing, medals for all finishers and a friendly festival vibe.

Saturn's 7 Hour Time Challenge at Wraysbury Skiff & Punting Club (Wraysbury, TW20) is an inclusive, self-paced race along the River Thames. Entrants choose a distance from a 3 km lap, with full laps around about 7 km (4.37 miles) or a short..

The Testway Ultra is a challenging ultra marathon held in Hampshire, England, featuring 40 and 50-mile distances along the scenic Testway footpath. The route stretches from the chalky downs near the Northern Hampshire/Berkshire border to th..

Join the Mortimer 10 km on Monday 6 April 2026 for a scenic two lap off road route through local woodlands, with a dog friendly canicross option. Enjoy chip timing, medals and a lively event village while supporting Ollie Young Foundation.

Challenge yourself on an 8 mile undulating trail around Freshwater, climbing about 900 feet and passing iconic spots like Tennyson Down and Alum Bay. Limited to 175 entries on 6 April 2026, this rugged multi terrain route offers stunning co..

Spring Run the Seasons at Cowdray Estate on 11 April 2026 offers scenic trails across the South Downs, with 5k, 10k and 10 mile races plus canicross. The 10k scores in the series and routes showcase heathland and big views.

Take on the iconic South Downs Way 50, a 50 mile trail race on 11 April 2026 from Worthing to Eastbourne. Expect 85 percent trail, 5700 ft of climbing, sweeping chalk ridge views and a finishing lap on the Eastbourne Sports Club track.

Run the Henley River Half Marathon, 10K or Junior Race at Temple Island Meadows and enjoy scenic, mixed terrain trails along the River Thames. Expect themed medals, free photos and a lively event village with food, drink and family fun.

Run the Rosebud Marathon, a scenic 26.2 mile leg of the Rose of the Shires Ultra across Northamptonshire with roughly 60% trail and 40% road. Enjoy varied terrain, aid stations and live GPS tracking to Brixworth Country Park.

Run the Rose of the Shires Ultra, a 54 miles circular route from Brixworth Country Park around scenic Northamptonshire. Mixed trails, canal towpath and road make for a rugged UTMB Index 100K with relay and Rosebud Marathon options.

Take on four iconic Centurion 50 mile challenges across 2026 with the 50 Mile Grand Slam package, starting with South Downs Way on 11 April. Secure your spot when entries open 26 April 2025 for a season of epic trails and camaraderie.

Tackle 28 miles along the traffic free Brampton Valley Way on 12 April 2026, choosing to start from Market Harborough or Northampton for a scenic out and back challenge. Expect quiet trails, two tunnels so bring a head torch, feed stations..

Run a scenic 10k trail loop through the Nene Valley countryside, over green fields, farm tracks and old railway lines. Fully marked with an aid station, this spring race is ideal for runners wanting a country escape.

Discover the Spring Trail Series on the Serpent Trail in the South Downs at Cowdray estate on 18 April 2026. Choose from 12 km to 110 km and enjoy a fully marked, supported route through greensand hills, rivers, woodland and heath.

Discover the Windsor 50 Ultra Challenge, a looped Great Park and Thames Path event offering 10 km, 25 km and 50 km options with Castle views and support along the route. Walk, jog or run from Windsor Racecourse and enjoy a lively festival a..

Tackle the Chiltern Ridge Classic 50K on 18 April 2026 along a scenic 51K Ridgeway route via Ashridge, Ivinghoe Beacon and Whiteleaf Hill. Limited to 400 runners, this UTMB race delivers big views, full support and a true trail challenge.

Take in Seaford seafront and rolling South Downs on the Martello Half Marathon, an undulating trail course that blends coastal views with countryside. Enjoy water stations, a bespoke medal and free event photos as you race.

Run the Thames Ring Series, a multi day trail loop based in Streatley on Thames that follows the river and canal towpaths on mostly flat, scenic terrain. Pick 100, 150 or 250 mile routes from 22 to 26 April 2026 for a true endurance fix.

Enjoy a scenic run or walk from Bath's southeast edge into Cotswold woods, hills and river valleys, choosing from four distances up to 26.5 miles. Finishers get a medal, food and drinks and recovery transport if needed.

Blindfolded and dropped at an unknown location, The Drop in Winchester challenges solo runners and teams to find their way back over 10 or 15 miles as the crow flies. No maps or GPS allowed, just navigation, grit and a taste for adventure.