Cheltenham
Trail Running Calendar near Cheltenham 2026-2027
Explore the top trail runs near Cheltenham for 2026-2027! We've gathered 93 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A single-stage 102 mile trail race along the Cotswold Way from Chipping Campden to Bath with a 32 hour time limit and on-course support.
A 24 hour trail ultra in Berkeley, Gloucestershire of about 130 miles across five roughly 26 mile laps with about 15,000 ft of ascent.
A trails half marathon through the Forest of Dean on 27 September 2026, organised by the Rotary Club with way-marked routes, chip timing and proceeds to charity.
October 2026
Wild Run Cotswolds showcases rugged off road trails on a private estate with fully marked routes, chip timing and a family friendly supporter zone. Entries are limited to 600; choose 10K, half, marathon or the six hour 360 challenge.
New off road 10 km along the River Wye near Ross on Wye on 4 October 2026, featuring wildlife, nearby facilities, £14.99 entry and a finisher medal.
Inflatable obstacle course in Cheltenham on 10 October 2026 offering 2.5k to 15k options, music zones, medals and family friendly participation rules.
A 55 km forest ultra on 10 October 2026 at Beechenhurst, featuring technical single track, open river stretches, on-course aid and a separate canicross category.
Trail race in an Area of Outstanding Natural Beauty around Biblins Youth Campsite, Ross-on-Wye covering approximately 6 miles or 10k on mixed trails and single track. Entry is limited to 200 runners and prizes include individual and team awards.
MacTuffX Swindon on 11 October 2026 offers solo, doubles and relay fitness races with 10x400m and 10x800m formats at Foundation Park County Ground in Swindon.
Run or walk a 10km cross country route through the woods and village of Walton Hall with electronic timing and a finish line roll included.
Seven consecutive offroad race days at Pengethley Manor from 19 to 25 October 2026 with a seven hour time limit each day and distances from 5k to ultra. Each day awards a unique Halloween themed medal and a virtual option is available.
An offroad Halloween race at Pengethley Manor offering 5k, 10k, half marathon, marathon and ultra distances with a seven hour time limit. In-person and virtual entries are available and paid verified finishes receive themed medals.
Part of a Halloween race series at Pengethley Manor, The Scary Scamper offers 5k, 10k, half, marathon and ultra options on a tough off road loop with a seven hour time limit and a virtual option worldwide.
Part of a Halloween series at Pengethley Manor, The Creepy Crawl offers 5k to ultra distances on an offroad, lap-based course with a seven hour time limit. Virtual entries and themed medals are available for paid participants.
A 5k night trail at Dunkertons Park in Cheltenham where runners use head torches to light the course. Open to ages 16 and over, with prizes for top three men and women and on-site refreshments and safety rules.
A Halloween themed offroad event at Pengethley Manor offering 5k, 10k, half marathon, marathon and ultra options with a seven hour time limit. In person and virtual entries are available and medals are themed to the series.
A Halloween series race at Pengethley Manor with 5k, 10k, half marathon, marathon and ultra options and a seven hour time limit. The offroad course runs inside the manor grounds and includes a hill and vineyard sections.
A Halloween series event at Pengethley Manor offering 5k, 10k, half, marathon and ultra distances on a tough offroad course with vineyard laps. Entrants have seven hours to finish and virtual participation is available.