Trail Running calendar near Southend-on-Sea 2025-2026

Join Plough and Harroween, a 5 mile Halloween night trail through Friston Forest on 31 October, starting and finishing at the Plough and Harrow in Litlington. Fancy dress, head torch and trail shoes required; medals, prizes and a pub drink..

Run 50 miles on an athletics track at Fireworks 50, a small field limited to 50 entrants with festival vibes, music, free tea and cake and a bespoke medal. Enjoy traffic free laps, aid stations and fireworks as dusk falls.

Join a guided 10 km trail run through the Chiltern Hills with Run The Wild, grouped by ability and suitable for runners who can cover 5 km non stop. Finish with a Tring Brewery tour, beer tasting and a bottle to take home.

Experience 50 km of rolling Norfolk trail along the historic Boudicca Way from Norwich to Diss on 1 November 2025. Limited to 150 runners, this winter ultra features checkpoints, hot drinks and a lively finish with a finisher medal.

Run under the stars at The Maverick Dark Hampshire in Alice Holt Forest on 1 November 2025, tackling 5 km laps along tree lined forest tracks with 5, 10 and 15 km options. Expect aid stations, chip timing, event photos and a metal finishers..

The ZigZag Catherine Wheel Canter is a unique running event held at Wodson Park Sports and Leisure Centre in Ware, Hertfordshire. Participants can choose from various distances including 5k, 10k, half marathon, full marathon, 50k ultra, or..

Run the Chiltern Ridge Winter 50K, a single loop through Ashridge and along The Ridgeway from Berkhamsted. Limited to 325 runners, with marked navigation and well stocked aid stations for a true autumn trail test.

Run the Leigh on Sea after dark 10k or 5k on 2 November 2025, with a juniors 5k for ages 11 to 15. Headtorches are mandatory, fancy dress is encouraged and every finisher gets a quirky not medal while proceeds benefit Southend YMCA.

The Wendover Woods Marathon, Half Marathon & 10k is a scenic autumn trail running event held in Wendover Woods, Buckinghamshire. The race features multi-terrain, hilly courses with significant climbs, making it a challenging yet rewarding e..

Autumn Amble is a scenic 7 mile self navigation trail around Great Dunmow on 2 November 2025, with HQ at The Butchers Arms. Choose your start time, follow the written route issued on the day, and celebrate at the pub finish.

Navigate ancient woodland, parkland and meadows at Dagnam Park in the HAVOC Regional and SWELL orienteering event with waterproof maps and SI timing. Courses suit beginners to experienced orienteers and help and coaching are available.

Take part in a woodland night score at Westerham: 60 minute navigation to collect as many 10 point controls as you can from 20 locations. Limited entries, book online in advance; apres and prize giving at The Carpenters Arms.

The The Druid's Challenge will take place in Tring on Friday 7 November 2025. You can run 86 miles.

Enigma Fireworks is a running event taking place on November 7th and 8th, 2025, at Caldecotte Lake in Milton Keynes. The event features both a marathon and a half marathon on each day, with participants completing scenic laps around the lak..

Run the Dirt Half Challenge in Leighton Buzzard this November, a scenic trail half marathon along canal towpaths, woodland and the Greensand Ridge. Finish with a lap of Tiddenfoot Waterside Park for a memorable autumn outing.

Tackle a 50 km ultra linking five classic long distance trails or choose a half marathon through chalk downland and woodland near Graffham. Enjoy stunning views, stocked checkpoints, SportIdent timing and an eco wood finisher medal.

The SATURN Remembrance Day Run 2025 - South is a commemorative running event held at Wraysbury Skiff & Punting Club, Egham, along the scenic River Thames. Participants can run a flexible distance within a 6 hour and 32-minute timed challeng..

Run Henham brings light trail running to scenic Henham Park in Suffolk near Southwold, with 10 km, 5 km and 1 km options. Expect chip timing, a bespoke medal and race tees for a fun day out.

Remembrance Sunday 2025 is a unique running event scheduled for November 9, 2025, in Brightlingsea, Essex. Participants can engage in a traffic-free, looped trail course, with options to run a marathon or half marathon within a six-hour tim..

Scenic timed loop around Canvey Island via sea wall and coastal path, starting and ending at Waterside Farm Leisure Centre. Counterclockwise, self supported and with a pub check in near 10k for a top up and friendly course sweep.