Trail Running calendar near Chiltern Hills 2026-2027

A series of marked trail races around Stroud and the Cotswolds using towpaths, commons and old railway lines, with checkpoints, water stations, marshals and map/GPX support.

A multi terrain 5 km race at West Lodge Farm in Desborough that passes fields, nature trails and farm animals, with a bespoke finisher medal and a virtual entry option to receive the medal by post.

A 50 mile point to point trail run along the North Downs Way from Farnham to Knockholt Pound, with 5,600 ft of ascent, six aid stations and a 13 hour cut off. Pacers and crews are not permitted and finishers receive a medal.

Compton Harriers stage the Compton Downland Challenge on 16 May 2026 with a multi-terrain full marathon (26.8 miles) and a 16 mile route across the Berkshire Downs. The event includes aid stations, a seven hour limit and a hand-thrown finis..

Join the Semington Slog on 16 May 2026 for a scenic 10K or family 2K around the village, canal towpath and leafy lanes. A friendly community fundraiser at St Georges School with marshalled routes, children’s activities and tasty food, plus..

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.

Trail running from Sudeley Castle in the northern Cotswolds with routes from 7 km to 51 km, marked trails, outposts and mandatory kit for longer courses. The event uses reusable cup policy and provides parking, bag drop and timed results.

A measured 10 km cross country run in Priory Park, Reigate on 17 May 2026 with a 250 metre section plus four laps, water stations, first aid and registration on the day. Trophies and a bespoke medal are awarded and the event supports Sport..

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 community running event in the parish of Deddington offering 5k, 10k and 20k routes on Sunday 17 May 2026. The event is open to all and supports local organisations including the Deddington Primary School PTA, Deddington PFSU and Deddingt..

Stort10 '26 at Cammas Hall Farm on 17 May 2026 offers scenic 10 and 5 mile off road loops through farm tracks and woodland with a friendly low key vibe. Finishers get a medal and a premium T shirt or a tree planted in their name.

Take on 18 miles of scenic Suffolk countryside from Nowton Park to Clare Castle Country Park, running or walking at your own pace. With a friendly atmosphere, medal for all finishers and support for St Nicholas Hospice, this is a challenge..

The The Newchurch Nine will take place in Newchurch on Sunday 17 May 2026. You can run between 5 and 9 kilometers.

An evening event at Chelmsford Brew Co offering a GPX/Strava 10 km trail run or a relaxed hike, with entry including a drink, crisps and a finisher's medal; under 18s are not permitted.

A multi-distance trail event from Richmond upon Thames to Brighton on 23 to 24 May 2026. Distances include 100 km, 50 km, 25 km and 10 km with marquee rest stops, medical support, GPS tracking and optional camping.

A multi-distance trail festival at Grimsthorpe Castle Estate offering 10 mile, 40, 70 and 100 mile options plus a 100 mile team relay on a marked 10 mile loop through woodland, limestone tracks and estate roads.

A Surrey trail running event on 23 May 2026 offering 20K, 41K and 62K routes that all finish at Burys Field, Godalming, with marked courses, regular aid stations and an 11 hour cutoff policy.

Run 145 miles non stop along the Grand Union Canal from Birmingham to Little Venice on a fully waymarked towpath. Limited to 100 starters with supported or unsupported entries and a 45 hour cutoff, it is a classic long distance challenge.

A 26.2 mile trail marathon in Richmond Park with three laps starting and finishing near Sheen Gate. The route follows the Tamsin Trail and inner park paths and features drink stations, chip timing and signposted routes.

Queen of the Suburbs Ultra invites runners to explore Ealing's greenways, towpaths and parks with 50k and 25k single loop options. Expect a Horsenden Hill climb with city views to Wembley and a friendly local race atmosphere.