Trail Running calendar near Maidstone 2026-2027

Join Esher Street O, part of the Winter Street O Series by Mole Valley Orienteering Club, at The Wheatsheaf in Esher. Choose a 60 or 40 minute score course with MapRun and relax with food and after the race refreshments at the pub.

Join the STAR Backyard Holmbury St Mary three hour trail challenge on 23 January 2026 and see how many 5 km laps you can complete around Holmbury Hill. A headtorch is required and entry includes a warm bowl of chilli or curry.

Brutal at Bagshot on 24 January 2026 is a gritty, hilly off road challenge on the Army Alpine circuit with bogs, knee to waist deep water holes and twisting, zigzag climbs. Pick a 5 km single lap or test yourself over two laps for 10 km.

Huffin Puffin Run on 24 Jan 2026 at Xcel SPORTS HUB, Walton on Thames. Flat 5.3 km riverside loop with distances from 5 km to ultra; lap as you like within the time limit and enjoy aid stations and digital results.

Pick your distance on the day at Running Tribe Races in Chalfont St Peter and tackle looped trails through woods and footpaths. Distances from 7 km up to marathon and ultra are offered, with an aid station serving food and drinks.

Take on the Ashdown Forest 10 and 5 Mile on 25 January 2026 at Pippingford Park, a scenic trail run through rolling forest terrain with rewarding climbs and wide open views. Free parking, medals for all and cash prizes for podium finishers..

Take to flat, scenic trails through Alexandra Gardens beside Windsor Castle with chip timing and friendly post race goodies. Choose 10K or half marathon, enjoy well marked routes, free photos and an event village for food and drinks.

The Trail des 2 Baies (D2B) will take place in Le Touquet-Paris-Plage on Sunday 25 January 2026. You can run between 24 and 40 kilometers.

Enjoy a scenic 8.5 km trail loop around Northiam, passing Great Dixter, rolling fields and woodland and a final uphill to the village hall. With just 60 places, marshals on course and tea and cake after, this intimate winter race is a delig..

G3 no.2 brings a friendly winter race to Hound House Road, Surrey on Saturday 31 January 2026. Pick a 10 km or 15 km route and enjoy clear signage, field parking and a welcoming series atmosphere.

Enjoy a scenic 10K through Lavenham's old railway line, forest trails and quiet rural roads on Sunday 1 Feb 2026. All finishers earn a medal and top three men and women take trophies in this cupless, friendly trail race.

Run a 48 mile point to point ultramarathon along the scenic Peddars Way from Knettishall Heath to Holme next the Sea on 1 February 2026. Enjoy remote rural paths, on course support and a bespoke wooden finishers medal.

Run through Bedgebury National Pinetum on undulating pine forest trails with 10 mile, 5 mile and junior options on 1 February 2026. Enjoy bespoke medals, free photos, trophies and easy parking by GoApe for a winter trail challenge.

The 6 Miles de Pont de Briques will take place in Saint-Étienne-au-Mont on Sunday 1 February 2026. You can run 10 kilometers.

Join the Dry January 10k at Willen Lake, Milton Keynes on 1 February 2026 to run 5k or 10k in person or virtually while supporting Alcohol Change UK. Enjoy a bespoke medal, charity technical t shirt and a fun lakeside route.

Guided 10 km trail run around the Devil's Punchbowl in Hindhead, with summer sunset runs and headtorch group night runs in darker months. Social pace, great views and the chance to try trail gear.

Dark Rose is a 5.5 mile trail race around Great Waltham with a small 75 runner field and self navigation route given on the day. Finish back at the Rose and Crown for a hearty cottage pie or vegetable lasagne.

Midweek street orienteering in the Essex Winter Series with 60 or 40 minute score courses across streets and open fields. Use MapRun with an Anytime catch up and earn bonus points for running on the night; bring a torch.

Take on KNC 16 Folkestone Urban on Thursday 5 February, a 60 minute score orienteering through the town centre and harbour with twisty streets, paths and hills to test your navigation. Entries open 30 January via online registration.

The Pilgrim Challenge will take place in Farnham from Saturday 7 February 2026 to Sunday 8 February 2026. You can run 66 miles.