Trail Running calendar near Cheltenham 2026-2027

Part of the 7 Deadly Sins series, The Envious Run takes place at Pengethley Manor on 17 January 2027 with lap based offroad routes from 5k to ultra. Runners and walkers have seven hours to complete their chosen distance and a virtual option..

A January off road 9.6 mile run across trails, fields and woodland with about 80 percent off road terrain. The event uses chip timing, has one water station at Littleton upon Severn and a 2.5 hour expected run time limit.

Looped races at Chalfont Park Sports Club and Chalfont St Peter Community Centre let runners choose distances from single 7K or 10K laps up to ultramarathons, with drop bag access, aid stations, crew support and on-site medical cover.

A six-hour self-paced lap event at Ryton Pools Country Park with a 3.3 mile runnable loop, canicross and rucking options, tiered entry fees and a charitable donation to Roald Dahl’s Marvellous Children’s Charity.

A weekend of running on the traffic free Tissington Trail near Ashbourne, offering a half marathon and a 10k with a gentle uphill outbound and slight downhill return, route maps and GPX files available, medals and free photos included.

The Holly Challenge on 23 January 2027 offers 5K, 10K, half marathon and marathon on the lanes of Lightmoor Nature Reserve near Telford. Entries are limited to 50 places and all finishers receive a medal.

A winter trail event at Moors Valley Country Park on 24 January 2027 offering a half marathon and 10.6 km options, with canicross choices and an eco-friendly wooden finisher medal set amid mixed woodland terrain.

Looped races at Chalfont Park Sports Club and Chalfont St Peter Community Centre let runners choose distances from single 7K or 10K laps up to ultramarathons, with drop bag access, aid stations, crew support and on-site medical cover.

Uphill winter trail at Irchester Country Park offering 5K, 10K and 15K on varied multi-terrain through a Jurassic landscape.

A seven hour time challenge at Dare Valley Country Park offering distances from 3 km to 50 km, with medals, aid stations and vegan goody bags.

A 7 to 8 mile cross country run around May Hill in Gloucestershire with steep climbs, muddy trails and an open plain at the summit. A Sunday May Hill Mayhem option adds an extra loop to total 14 to 15 miles.

A twilight trail run in Hurn Forest offering 5 or 10 mile out-and-back laps, head torches required, trail shoes recommended, and 20% of entry fees donated to Forestry England.

A field-start running event in Surrey on 30 January 2027 offering 10 km and 15 km options with on-site parking and series bundle entries, organised by G3 Series.

Looped races at Chalfont Park Sports Club and Chalfont St Peter Community Centre let runners choose distances from single 7K or 10K laps up to ultramarathons, with drop bag access, aid stations, crew support and on-site medical cover.

Guided *10 km* trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.

A six hour lap event at Daventry Country Park where participants complete as many 3.3 mile laps as they choose within the time limit. Canicross and rucking are allowed and the route is mostly crushed stone with on-site parking, a cafe and t..

A seven hour time challenge along the River Thames with distances from 3km to 50km, medals and pins, mixed path and trail terrain.

A night race at Westonbirt National Arboretum on 6 February 2027, with scenic routes through tree collections and firm trail-like surfaces. Distances include 5 km and 10 km; tickets are currently sold out.

A two day 66 mile winter trail event on the North Downs Way with marked routes, staffed aid stations, overnight accommodation and luggage transfers.

A Backyard Ultra near Crickhowell mixing 50/50 trail and tarmac on a 4.167 mile loop, eleven timed laps then a final race to decide the winner.