Trail Running calendar near Gerrards Cross 2026-2027

A hilly, scenic trail event in the South Downs offering 10 km and 20 km senior races plus 3 km and 5 km junior races. Routes follow footpaths and bridleways, are marshalled and include water stations and age category awards.

A multi terrain community event on 10 May 2026 at Dilton Marsh playing field offering 10 km, 3 km and a 1/2 km fun run with medals for finishers, prize categories, water stations and basic facilities.

A guided 30 km trail run in the Chiltern Hills with trail technique instruction, checkpoints, a finisher’s medal and Trees not Tees certificate, based near Tring Station with limited spaces.

A trail running event conceived to increase participation from Black people, people of the global majority and allies. It offers 1K, 5K and 10K distances, children's entries are free under 16, and the day includes food, live music and activ..

Hairy Legs is an all ages cross-country event at Sheepcot Recreation Ground on 10 May 2026, with children's laps, teenage and adult loops plus solo and relay options, and proceeds supporting two local primary schools.

A one lap *10 km* trail through Hampton Estate and Puttenham Common with undulating hills and bluebell woods. Chip timing, finish medals and on-site parking, with food and refreshments available at the finish.

A multi-distance trail event in the Cotswolds on 10th May 2026, featuring quarter, half, marathon and Ultra 40 routes across trails, towpaths and commons with marked routes, checkpoints and on-course water.

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 roughly 5 mile single lap trail through Stowell Park and the Coln Valley near Chedworth Roman Villa. The multi terrain course includes footpaths, fields and a river crossing and has a 2 hour 30 minute finishing limit.

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.

A family fun run and a five mile all terrain race across National Trust parkland, marshalled with chipped timing and medals; proceeds fund school equipment, trips and PE provision.

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 evening summer series at Dinton Pastures with 5 km and 10 km races plus a 2 km kids event. Off road and traffic free, the series offers chip timing, finisher medals, instant results and on site first aid.

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 on 16 May 2026 offering laps of a 2.5 km circuit with 2.5 km, 5 km, 10 km and 15 km options, music zones, water stations and a finisher medal.

The Semington Slog on 16 May 2026 features a 10 km and 2 km run from St Georges School. Routes explore the village and Kennet and Avon Canal towpath. Enjoy community activities, refreshments, and prizes.

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.