Trail Running calendar near Cheltenham 2025-2026

Creepy Crawl on 21 October 2026 at Pengethley Manor offers 5k to ultra distances on a challenging off road loop through hills and two vineyards. Ideal for runners and walkers craving a scenic, gritty test of endurance.

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.

Take on distances from 5k to ultra on an off road, multi lap course set inside the grounds of Pengethley Manor near Ross on Wye. Each 2.5k lap includes a hill and rolling vineyard terrain, welcoming runners and walkers.

Take on the Thames Trail Ultra, a scenic 47 mile point to point along the Thames Path from Iffley to Henley on Thames. Mostly riverside trails and country paths, this supported ultramarathon pairs stunning views with a rewarding challenge.

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 Zombie Shuffle at Pengethley Manor on 25 October 2026 for offroad laps through vineyards and rolling hills, with distances from 5k to ultra to suit walkers and runners. Finisher medals and virtual entry options make it easy to join..

Join Irchester Spooktacular, a Halloween night run through woodland trails with a 5k and a 2k family fun run. Fancy dress, themed marshals, finishers medals, Halloween chocolates and free event photos make it great family fun.

The Chiltern Ridge Winter 50K will take place in Berkhamsted on Saturday 31 October 2026.

Run Wendover Woods on challenging, hilly forest trails with marathon, half marathon, 10k and junior distances across mixed terrain. Enjoy onsite facilities like a cafe and plenty of parking plus bespoke medals and free race photos.

The Enigma Fireworks will take place in Caldecotte from Friday 6 November 2026 to Saturday 7 November 2026. You can run between 21 and 42 kilometers.

Run the Remembrance Run 2026 South along the River Thames at Wraysbury in a reflective 7 hour lap challenge where you pick your distance. A two minute silence adjusts official times and finishers of 3 km or more earn medals.

Run under the stars through the rolling Chiltern Hills at Stonor Park in November with three waymarked trail options from 7 to 17 km. Expect a fully marked, timed night race; bring a headtorch and enjoy a finishers medal and event atmospher..

Run the Maverick Oxfordshire Trail at historic Stonor Park in the Chilterns AONB with 7 km, 13 km or 22 km routes through deer filled woods and under soaring red kites. Expect steep climbs, wild views and fully marked, timed trails.

Run from Alexandra Gardens in Windsor along flat, fast off road trails through parkland and woodland. Choose 10K or half marathon with chip timing, free photos and an event village serving food and giveaways.

Remembrance Run at Wraysbury on the Thames is a timed 7 hour challenge where you choose any distance from 3 km to ultra. Scenic signed laps, aid stations with vegan options, a finisher medal and a two minute silence at 11:00.

Explore ancient woodland and open heath in the New Forest with 10 km, 17 km or 22 km trail options. Enjoy waymarked gravel paths, on course support and a finisher medal, and note water stations are plastic free so bring a reusable cup.

Run the North Chilterns 50K, a scenic trail ultramarathon from Putteridge Bury over Warden, Barton and Pegsdon Hills with sweeping views. Limited to 250 runners, this supported 50 km course is a rewarding late autumn challenge.

Join a guided 10km trail run around the scenic Devil's Punchbowl in Hindhead, with climbs and a summit pause to soak up the view. Enjoy sunset sessions or headtorch night runs led by an experienced trail coach in a friendly group.

Enjoy a scenic winter run around Carsington Water with half marathon and 10K options on Saturday 5 December 2026. Undulating reservoir trails, kilometre markers and a themed medal make this RunThrough event a rewarding lakeside challenge.

Mad Running Junkies' Nightmare Before Xmas Trail half marathon on 19 December in Aberkenfig, Bridgend offers a festive mixed trail with mud, climbs and scenic views. Enjoy mince pies, a bespoke medal and prizes for the best fancy dress.