Cheltenham
Trail Running Calendar near Cheltenham 2026-2027
Explore the top trail runs near Cheltenham for 2026-2027! We've gathered 89 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
January 2027
A multi distance off road event at Pengethley Manor with a seven hour time limit for chosen distances and an on site or virtual option. The course uses 2.5 km laps and includes vineyard terrain and a hill.
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 is availa..
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.
Timed multi-lap run on a 2.62 mile canal out and back in Brimscombe with distances from 5 km to ultra and a seven hour limit; medals for all participants.
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.
February 2027
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 5km and 10km run through Westonbirt Arboretum on 7 February 2027, with firm trail terrain and routes through areas showcasing over 2,500 tree species. The event is family friendly and tickets are currently sold out.
Choose your distance from 5k to Ultra on a tough off road course at Pengethley Manor. Experience vineyard trails with a seven hour time limit and unique medal options for individuals or pairs.
A timed event on a 2.62 mile out and back canal route with flexible rock up and run starts. Distances range from 5 km through marathon and beyond, with a seven hour time limit and a finisher medal for all.
A 12 mile cross country race in Dursley on 21 February 2027 with over 2000 feet of climbing across woodland trails, mud, roads and steep climbs.
Map and compass adventure in the Cotswolds combining trail running and mountain biking with flexible score formats and bike hire available.
A navigational challenge in Worcester where participants are blindfolded and dropped at an undisclosed location, then must find their way back over measured distances of 6, 10 or 15 mile. Optional live GPS tracking is available for safety and viewing..
Off road Standard and Sprint duathlons plus 5 km and 10 km trail runs in the Forest of Dean with live chip timing and on-site parking.
March 2027
A six hour trail event at Symonds Yat where runners complete as many 5.25 km loops as possible, each with about 160 m of ascent.
Hill race at The Hostelrie, Goodrich on 20 March 2027: about 8.6 km with 335 m climb on a partially marked course; entry £5 members, £6 non-members.
Measured forest trail half marathon in the Forest of Dean with chip and gun timing, three water stations, age group prizes and proceeds donated to charity.
April 2027
Trail event in Monmouth on 3 April 2027 with full and half options, varied terrain, aid stations and a 4.8 average rating from 31 reviews.
Guided 18-mile trail run along the Malvern ridge with over 1300 m ascent, meeting at North Quarry Car Park in Great Malvern; group pace, kit guidance and route support provided.