Trail Running calendar near Maidenhead 2026-2027

A 30 mile out and back ultra along the River Stort and Lee navigations on the Hertfordshire Essex border, mostly flat grassy and gravel trail with checkpoints every 5 miles, electronic timing, medals for finishers and trophies for top three..

A hip hop themed coastal run at Milford on Sea offering flexible distances from 5K to ultra and 5.3 km laps, with aid stations, a cupless policy, bag drop and a themed medal.

Pumpkin Plod at Ferry Meadows is a multi-hour lap event on a 5.3 km mixed-surface loop where runners complete as many laps as they choose. Aid is provided each lap and finishers receive an event medal.

A timed, self-supported anti-clockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre, with a pub check at about 10 km, a four hour cut off, and a route mainly on sea wall and coastal paths.

ATW Grafham 5K and 10K take place at Grafham Water Visitors Centre on 25 October 2026. Entry fees range from £24 to £33, the races run alongside the ATW Grafham Duathlon, and camping is available the night before.

Looped races at Chalfont Park and Chalfont St Peter let runners choose distances from a 7K loop to multi lap ultras. Aid station, clear course marking, crew support and medical cover are provided.

Essex Walker offers a 26 miles figure of 8 route and an 18 miles variant on footpaths and bridleways around Blackmore. It is part of the Essex and Herts Triple Challenge and includes checkpoints, refreshments, and a finishers certificate.

A Halloween themed night run at Irchester Country Park featuring a 5k race and a 2k family fun run, with finishers medals, free event photos and Halloween treats.

A five mile night trail run at The Plough and Harrow in Litlington on 30 October 2026, self navigated via GPX with a tail runner, timed results, Halloween fancy dress prizes and an age limit of 18 plus.

A single-loop 50K trail race on 31 October 2026 starting and finishing in Berkhamsted. Fully marked route with three aid stations, about 800 m of ascent, a nine hour time limit and a 350 runner field.

Experience a festive 6.66 km Halloween trail run starting and finishing at a local brewery in Chelmsford. Participants enjoy a costume focused event with medals and drinks for finishers in a social atmosphere.

Nighttime trail laps at Alice Holt Forest on 31 October 2026 with 5 km, 10 km and 15 km options. Fully marked and timed courses include one outpost per lap and on-site facilities such as parking, food and a finisher medal.

An evening Halloween trail at Hogmoor with kids and adult loops: 3.3K, 6.6K (including canicross) and 10K. The sandy, muddy course features oversized statues, on-site playground, free parking and medals for finishers.

A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.

A coastal run on West Wittering Beach with panoramic sea and Downs views. Offers three distances 15.3k, 10k and 5k, chip timing, on-course water, finisher medals and a canicross option.

Forest trail races at Wendover Woods on 1 November 2026 include marathon, half marathon, 10k and a junior run over a multi-lap 10 km course with varied, hilly terrain and on-site facilities for spectators.

A 10 mile off road trail in Stonehouse near Stroud on 1 November 2026, starting with about one mile uphill followed by nine miles of undulating muddy trails. Canicross runners are welcome and there is a 2 hour 30 minute cutoff.

An out-and-back 5 mile night and dawn running event through the 422 m Oxendon Tunnel with mood lighting and headtorch required. Finishers receive medals, prizes are awarded, on-course support and refreshments are provided.

Two days of marathon and half marathon races around Caldecotte Lake in Milton Keynes on 6 and 7 November 2026, with multi-lap clockwise courses, on-course water and toilets, enforced time limits, and bespoke finisher medals.

Take on flat, scenic laps along the Thames towpath in Walton on Thames with flexible starts and distances from 5 km to ultra. Limited places, aid stations, digital results and medals make this a friendly, festival style challenge.