Trail Running calendar near Chipping 2026-2027

Explore the beautiful Chiltern Hills on this guided 30km trail running adventure. Enjoy 500m of ascent through woodlands and ridges with professional run leaders and a finishers medal included.

An inclusive UK trail running series offering 1K, 5K, 10K and kids races with free entry for under 16s, held at Dunstable Downs in May and Blaise Castle Estate in October 2026, with activities, food and live music.

Hairy Legs is a cross-country charity event for all ages, held on a scenic, hilly woodland course. Distances are based on unmeasured loops, and there are solo, relay, and shorter youth options. Fancy dress is encouraged, with prizes and a f..

Experience a scenic single lap trail race through the bluebell woods of Hampton Estate and Puttenham Common. Enjoy chip timed racing with bespoke medals and onsite refreshments in a beautiful Surrey setting.

A community 5k trail run and walk around East Hendred with a separate 1k kids event on the Sportsground. Entries are limited and close on 8 May 2026.

A cross country event in Little Gaddesden on 10 May 2026 offering 10K, 5K and mini races for under 7s. Pre registration and on the day fees apply and medals are awarded to all finishers.

A self‑navigated trail event in Thaxted on 10 May 2026 raising funds for Thaxted Windmill restoration. Two route options are offered, 5 miles (8k) and 8.25 miles (13k), with entry fees and a refreshment voucher included.

Race 2 of the Northants 5 km Series is at West Lodge Farm in Desborough on multi terrain routes through fields and nature trails. Finishers receive a bespoke medal; parking is free and on site refreshments are available.

A measured off-road 5K on 13 May 2026, Race 2 of the seven-race Crown to Crown series, run mainly on bridleways through Willow Park with limited parking and on-course safety support.

A four-race summer series at Dinton Pastures offering 5 km, 10 km and a 2 km kids event across May to August. Organised by Barnes Fitness with chip timing, marshals, medals and pre bookable parking.

A coastal point-to-point trail event in Suffolk and Essex offering 100 mile, 50 mile and 50 km options with GPS tracking, regular checkpoints and a mandatory kit list. Routes run mostly on soft dirt trail through protected landscapes.

A 50 mile point to point run on the North Downs Way from Farnham to Knockholt Pound with 5,600 ft of climb, six aid stations and a 13 hour limit. Entry requires a prior marathon finish within that race’s cut off.

The Twenty Sixth Compton Downland Challenge in Compton, Berkshire on 16 May 2026 features a full marathon and a 16 mile race with a seven hour time limit; route maps, elevation profiles and videos are provided.

An inflatable obstacle course at Brands Hatch Race Track on Saturday 16 May 2026 with 2.5 km laps and distance options to 15 km, music zones, water stations, on-site parking and charity partners.

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

A timed lapped event at Mowsbury Park on 16 May 2026 offering distances from 5 km to ultra with a seven hour time limit, flexible start window and both medal and no medal entry options; places capped at 75.

A weekend obstacle race in Henley on Thames on May 16-17, 2026, featuring Sprint, Super and Beast distances plus a Kids Race and spectator tickets, run along historic town landmarks and a riverside course.

A 5 km muddy obstacle course at Braunstone Park on 16 May 2026 where participants climb, crawl and slide through a circular course. Minimum age 13, limited weather-dependent parking, and a minimum fundraising target of £50.

Race for Life Brentwood at Weald Country Park on 16 May 2026 offers 3k, 5k and a double lap 10k across grass and woodland trails. The event is chip timed and carries a minimum fundraising target of £50.

A measured cross country 10 km at Priory Park, Reigate on 17 May 2026, organised by MCC Promotions. Facilities include water stations, first aid, bag drop and trophies, and the event supports the charity Sport In Mind.