Trail Running calendar near Aylesbury 2025-2026

We have found 388 Trailruns within 80 miles of Aylesbury. See below where and when you can find the races.

The Windsor 50 Ultra Challenge invites participants on scenic loops through Windsor Great Park, along the Thames and past Windsor Castle. Choose 10 km, 25 km or 50 km courses with app tracking, support stops and a lively finish celebration.

The Chiltern Ridge Classic 50K is a scenic trail ultra on 18 April 2026, from Berkhamsted Castle to Hampden Meadow in Wendover. Follow the Ridgeway past Ivinghoe Beacon and Ashridge for an off road challenge with on course support.

UTMB Index

Martley Madness is a scenic 10 mile trail run in Worcestershire through woodland, Rodge Hill climbs and a stretch of the Worcestershire Way. Chip timing, bespoke medals and post race cake await while proceeds support Cardiac Risk in the You..

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.

The Trident Grantham Triathlon will take place in Grantham on Sunday 26 April 2026.

The Drop - Winchester is a unique and challenging race held in Winchester, UK, offering participants a choice between 10-mile and 15-mile distances, either solo or in teams. Inspired by military-style navigation, the event requires runners..

Eastnor Castle Backyard 8hr and Relay 2026 is a running event staged in the private Eastnor Castle Deer Park, set within the Malvern Hills National Landscape. The route runs along a private estate road in a figure‑of‑eight, with stunning vi..

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.

Run a flat, fast 5K or 10K along the River Adur and Downs Link at Adur Recreation Ground in Shoreham by Sea, passing the airfield and Toll Bridge. Chip timing and finishers medals add to this well supported riverside race.

Take on the Coventry Way Challenge on 26 April 2026, a scenic 40 mile cross country route starting and finishing at Heart of England Social Club in Meriden. Solo or relay entries include checkpoints, live tracking and a finisher certificate..

May 2026

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..

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 a guided 30 mile trail ultra from West Hanger, Guildford, led by an experienced ultra coach, tackling Box Hill, Leith Hill and Greensand Way. This friendly group run suits runners who have completed at least 22 miles in training.

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.

Take on the Thames Path 100 on 2 May 2026, a point to point 100 mile trail from Richmond to Oxford. Scenic riverside paths, aid stations and a 30 hour limit await as you chase centurion buckles and a memorable university finish.

UTMB Index

Take on the Malvern Hills Ultra on 2 May 2026 from Abberley Village Hall, choosing from 23, 31, 38 or 47 mile routes along the Worcestershire Way. Tough scenic trails, UTMB points, GPX navigation and a bespoke medal plus technical tee await..

Rapid Relays is a dynamic running event held at the scenic Culden Faw Estate in Fawley, near Henley on Thames, Oxfordshire. The race features a woodland trail course on estate tracks with gently undulating terrain, including a notable climb..

Tackle scenic South Downs trails at the Three Forts Challenge with full marathon, half marathon and five mile options calling at Chanctonbury Ring and Cissbury Ring. All profits support Ferring Country Centre and local charities.

Discover the Cotswolds on foot at Tempo Trail Races 2026, a scenic weekend of trail racing on 3 May with distances from 10K to 100 km, and a new 50K option. Friendly atmosphere, challenging routes and stunning countryside await.