Trail Running calendar near Cheltenham 2026-2027

Celebrate the 10th anniversary of this 5 mile chip timed trail and Canicross race. Run through the scenic Upper Wreake valley across fields and brooks with beautiful views over the Leicestershire countryside.

Enjoy a flexible 7 hour time challenge at Dare Valley Country Park with distances ranging from 3km to ultra marathons. Finishers earn a themed medal and doughnuts after running through scenic Welsh countryside trails.

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.

Experience a scenic trail half marathon through the Quantock Hills featuring technical forest paths and open moorland. This UTMB index event offers on site camping and a rugged course with stream crossings for all finishers.

Explore the scenic Hambleden and Stonor valleys with three distance options starting from Marlow. Enjoy a managed challenge event featuring checkpoint snacks and a finish line meal in the heart of the Chilterns.

Test your endurance at MacTuffX Brierley Hill in October 2026. Choose between 400m and 800m intervals in solo, double, or relay formats for a unique racing experience. This event is open to all participants aged 18 and over.

A flexible 6-hour timed run along the flat Jubilee River towpath. Run one 5.24-mile lap or see how many you can complete. The scenic route passes through countryside with views towards Windsor Castle.

Set in the scenic Sence Valley Forestry Park, this flexible 6 hour event allows you to run as many 3.3 mile laps as you choose. Experience a mix of woodland trails and lakeside paths with distances ranging from 5k to ultramarathon.

Test your endurance at Turvey House with a 6.7 km loop every hour on the hour. Choose to run solo, in a pair, or join the capped eight hour challenge in this unique last person standing format.

Experience the bouncy inflatable obstacle course at Cheltenham Racecourse. Choose between several distances and navigate through a series of large inflatables while earning your finisher medal.

Experience a 32 mile trail journey through the remote Cambrian Mountains and toward Lake Vrynwy. This sustainable event features a fully marked course with 4862 feet of elevation and a 14 hour cut off time.

Experience a 55 km journey through the scenic Forest of Dean featuring technical trails and river views. This self navigation ultra marathon offers dedicated support and a separate category for Canicross runners.

Discover the scenic trails of the Chiltern Hills in this guided 21 km autumn running adventure. Led by qualified guides, this event focuses on group camaraderie and trail techniques across beautiful undulating woodlands.

Run through the scenic woodland tracks of Cannock Chase Forest in this autumn festival featuring trail races for all ages. Enjoy chip timed results and a unique themed medal in a spectacular natural setting.

Choose a scenic 10k or shorter 5k through the Chiltern Hills around Frieth, combining woodland paths and country roads. Expect rolling climbs and panoramic views for a rewarding, hilly challenge for road and trail runners.

The FOOBS Trail and Fun Runs return in October. Choose from a chip timed 10K, 6K, or a family friendly 2K fun run through the countryside near Old Basing. The event supports local schools through community fundraising.

MacTuffX Swindon features a series of repetition based running formats including solo and team categories. Participants choose between multiple 400m or 800m loops in this structured athletic event for adults.

Experience an undulating trail run around the scenic Carsington Water reservoir. Choose between a 10k or a half marathon while enjoying sweeping views of the Derbyshire countryside and receiving a themed finishers medal.

A 100 mile trail race through Oxfordshire featuring four 25 mile out and back spurs. Runners navigate the historic Ridgeway and Thames Path trails supported by 16 aid stations and full medical coverage.

Join this flexible 7 hour time challenge at Dare Valley Country Park featuring distances from 3km to Ultra Marathon. Enjoy a well stocked aid station and earn a unique themed medal on scenic parkland paths.