Trail Running calendar near Milford 2025-2026

Take on the Stort30, a scenic 30 mile ultramarathon along the River Stort and Lee Navigation. Expect riverside trail with some muddy sections, checkpoints and club facilities for a friendly but challenging day.

Thames Path Trail Run : Windsor Racecourse, 26 October 2025 The Thames Path Trail Run takes place at Windsor Racecourse on 26 October 2025. The route follows sections of the Thames and nearby countryside. Distances offered: 21km 16km No do..

Trail Run Canterbury is a Canterbury-based trail and multi-terrain running event anchored at St Edmund’s School on St Thomas Hill. It offers three distances: 5.5, 10 and 20 miles. The route winds along trails around the edge of Canterbury,..

Experience Irchester Spooktacular, a night time Halloween run through woodland trails with costumed marshals and fancy dress prizes. Choose a 5k or 2k family run and collect a spooky medal and treats while supporting local foodbanks.

Enjoy a 60 minute score orienteering course through woodland and open slopes at Trosley Country Park on the North Downs. Choose from 20 controls, hunt bonus dumbbells and race the clock in scenic terrain.

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.

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..

WRNL Bovington on Saturday 1 November is event two in the Wessex Region Night League: a 60 minute score course across runnable woods, open heath and urban terrain. Fast, tactical night orienteering with marshalled road crossings.

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..

Tackle the Chiltern Ridge Winter 50K, a scenic trail ultra with about 800m of climb across Berkhamsted Common, Ashridge and The Ridgeway. Fully marked with aid stations, chip timing and finish showers for a memorable autumn challenge.

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.

Join the WIM Founder's Trophy at Bere Wood on Sun 2 Nov with courses for all levels. Expect runnable woods, marshy patches, waterproof maps and electronic punching for a fun day out. Entries close 31 Oct.

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.

Join WRNL 3 in Colden Common for a lively 60 minute orienteering score event where you pick controls in any order to rack up points. Lights and hi viz required; hired dibbers available and juniors must be accompanied.

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.