Trail Running calendar near Haywards Heath 2026-2027

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 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.

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 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 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.

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.

Run the scenic loop at Hurtwood Park Polo Club in Cranleigh, Surrey with distances from 5 km to ultra on mostly flat off road trails. Multi lap format and a seven hour time limit suit all paces and every finisher gets a memento.

A long running trail event at Cammas Hall Farm offering 10 mile and 5 mile loops across farm tracks and woodland, with water stations, marshalled road crossings and on site facilities.

Trail runs of 900 m, 4.5 km and 9 km around Newchurch, supporting Newchurch Primary School. All entrants get a medal and are entered into a raffle for prizes.

The Ridge Off Roader is a trail run through the scenic Chiltern Hills. It offers a half marathon and a 10k route, plus a fun 1k for kids. All proceeds support the local school.

Experience an annual five mile off road run through the scenic Little Haven Nature Reserve. This trail race features woodland paths and spring meadows while raising funds for local hospice care.

Off-road multi lap run at Nutbourne Vineyards with views to the South Downs. Choose distances from 5 km up to a half marathon on the day; entry is £29, places are limited to 100, and finishers receive a medal, drink and cake.

Mud Monsters Run on 17 May 2026 in East Grinstead is a muddy obstacle event with 3 km, 5 km and 10 km routes through fields, woods and river crossings. Finishers get a medal and free photos; onsite parking costs £5.