Trail Running calendar near Cheltenham 2026-2027

Join the Witches Whisk at Pengethley Manor for a spooky Halloween trail across 2.5 km laps through vineyards and rolling offroad terrain. Pick 5k to ultra distances, ideal for runners or walkers after a fun seasonal challenge.

Celebrate Halloween at Pengethley Manor with the Scary Scamper, an offroad multi lap course winding through vineyards and hill sections on the manor grounds. Distances from 5k to ultra welcome runners and walkers with a 7 hour time limit.

The Creepy Crawl is an offroad run through Pengethley Manor's vineyards with a hill each lap, offering distances from 5k to ultra and open to all. Pick your distance, finish within 7 hours and earn an onsite or virtual medal.

Join the Ghostly Gallop at Pengethley Manor on 22 October 2026 for a spooky offroad challenge through vineyards and rolling hills. Choose distances from 5k to ultra with in person or virtual entries and Halloween themed medals.

Join the Petrified Pootle, a Halloween off road run at Pengethley Manor offering distances from 5k to ultra for walkers and runners. Tackle hilly vineyard trails, soak up the spooky vibe and earn a finisher medal or run virtually.

Thames Trail Ultra on 24 October 2026 is a scenic 47 mile point to point run from Iffley near Oxford to Henley on Thames along the Thames Path and Ridgeway. Riverside trails, checkpoint support and live GPS tracking make for a classic autum..

Join the Spooky Sprint at Pengethley Manor, Ross on Wye on 24 October 2026 for a tough offroad Halloween race through two vineyards. Choose on course or virtual options from 5k up to ultra and enjoy a scenic, challenging looped course.

Join the Halloween Zombie Shuffle at Pengethley Manor on 25 October 2026 for off road fun through vineyards and hills. Choose a 5k to ultra, walk or run on a looped course with a 7 hour time limit and a virtual entry option.

Experience Irchester Spooktacular, a Halloween night time run through woodland trails with 5k and 2k family options. Fancy dress, themed marshals, medals, Halloween treats and free photos make it a spooky family favorite.

A series of linear mountain trail races across the Brecon Beacons and Black Mountains, offering four distances from 21 miles to 100 miles, marked checkpoints, GPS navigation requirements and drop bag options.

Chiltern Ridge Winter 50K, Saturday 31 October 2026, is a single loop trail from Berkhamsted through Ashridge and the Ridgeway with about 800 m of climbing. A UTMB index event ideal for experienced trail runners seeking scenic winter trails..

Night trail event in Alice Holt Forest offering choice of 5 km, 10 km or 15 km around tree lined tracks. One outpost per lap supplies snacks and refill barrels. Dogs and headphones are not permitted.

Run the Wendover Woods Marathon, Half, 10k or Junior 1k through autumnal forest trails. Expect a scenic but hilly multi terrain challenge with bespoke medals, free photos and on site facilities.

Tackle the Apocalypse Run, a rugged 10 mile trail through Stonehouse with a stiff opening climb and muddy, undulating terrain. Canicross runners welcome and all finishers get a medal for braving the off road challenge.

Run the November Nightmare in Telford from 1 to 8 November 2026 a unique eight day challenge where you can enter any single day or tackle them all. Daily courses of 8, 16 or 26.2 miles pass through Ironbridge and earn a medal each day.

Tunnel Vision is a 5 mile out and back that sends runners through the atmospheric Oxendon Tunnel with mood lighting. Pick a Night or Dawn run, earn interlocking medals and support local foodbanks.

Join Enigma Fireworks on 6 and 7 November 2026 for marathon and half marathon loops around scenic Caldecotte Lake. Enjoy waterside views, lap support and a bespoke finisher medal to light up your race season.

Take on flat, scenic laps along the Thames towpath in Walton on Thames with flexible starts and distances from 5 km to ultra. Limited places, aid stations, digital results and medals make this a friendly, festival style challenge.

A night trail run at Stonor Park near Henley-on-Thames with three route distances from 7 km to 17 km. Middle and long routes have one outpost each; bring a headtorch and a reusable cup; headphones are not permitted.

Three waymarked trail routes from Stonor Park through the Chilterns AONB, featuring steep sections, wildlife sightings, on-course outposts and event amenities including free parking, timing, results and a finisher medal.