Trail Running calendar near Rayleigh 2025-2026

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.

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 spring trails at Cowdray Estate with 5 km, 10 km, 10 mile, junior races and canicross options. Scenic sandy heathland and mixed trail sections through wildlife rich commons deliver a rewarding, characterful day out.

Take on the Haughley Festival of Running at Haughley Park Suffolk, with distances from 5k to ultra and a cap of 300 entrants. Enjoy undulating park and woodland laps, secure on site parking and a bespoke finishers medal.

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.

Run the Spring Trail Series at Cowdray Estate in Surrey, following the scenic Serpent Trail through greensand hills and woodland. Choose from 12km to 110km, with relaxed cut offs, campsite and on site expo for a friendly well supported day.

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.

Join the Grand National trail run in Findon Village with a 10 km main race, new 5 mile course, a 10 km canicross and a 2 km kids loop at Nepcote Green. This charity event features bespoke medals, free photos and a best dressed jockey prize.

Run the scenic Thames Ring, a multi distance trail loop from Streatley on Thames that follows the river and canals. Choose 100, 150 or 250 mile challenges on riverside paths with GPS tracking and checkpoint support, 22 to 26 April 2026.

Join the Ale Trail, a 15 mile run from the beer garden of Ye Olde Smugglers Inne in Alfriston on 26 April 2026 with pub checkpoints and a finisher's drink. Limited to 50 places, this social trail run includes GPX navigation and a 4 hour 30..

Take part in The Other Run in Bury St Edmunds on 26 April 2026 with 5k, 10k, half and marathon options on scenic country roads. Enjoy a bespoke finisher medal, friendly atmosphere and a seven hour marathon cutoff.

Join the 22nd Angmering Bluebell Trail through fragrant bluebell woods at Angmering Park Estate, with 10 km and 10 mile routes to choose from. Canicross welcome and finishers receive bespoke medals and free photos.

Saturn’s Midweek Chasing Numbers 7-Hour Time Challenge is held at Wraysbury Skiff & Punting Club on the River Thames. The event is designed to be affordable and flexible, inviting all abilities to run or walk within a 7-hour window. Partici..

Join the 2026 Heritage Run in Thorpeness on 1 May for scenic mainly off road 10k and half marathon distances, plus a dog run 10k. Organised by local volunteers, the event supports charity and has donated over £45,000 to date.

Take on the iconic Thames Path 100 from Richmond to Oxford, 100 miles of scenic riverside trails and historic towns. Enjoy waymarked routes, plenty of aid stations and a supportive ultra atmosphere for a true point to point challenge.

Join a guided 30 mile trail run along the North Downs Way and Greensand Way led by an experienced ultra runner and coach in a supportive group run. Enjoy sweeping hilltop views, shoe demos and a possible alcohol free beer at the finish.

Enjoy a three day running festival over the May Bank Holiday across three Mid Sussex towns. Run single town races or combine stages into the Mid Sussex Marathon, with undulating multi terrain routes, medals, family fun and fancy dress.

Join Run Silchester on 2 May 2026 for 2.5, 5 and 7 mile trail runs around the Roman wall, ancient woodland and a 12th century church. Family friendly festival atmosphere with stalls, music and proceeds supporting local community causes.