Trail Running calendar near Winchester 2026-2027

A point to point 47 miles ultra along the Thames Path and Ridgeway from Iffley to Henley-on-Thames, mostly on trails, with five aid stations, mandatory kit checks, baggage transfer and live GPS tracking.

A hip-hop themed coastal run at Milford on Sea with mixed terrain and coastal views. Runners choose distances from 5 km to ultra-marathon, completing 5.3 km out and back laps with an aid station and themed medal.

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.

Mendip Muddle is a 20 km multi terrain fell race in Somerset with about 420 m of climbing. Headquarters are at Charter House Outdoor Activity Centre; on course water and first aid are provided and prizes are awarded by category.

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 around the Chilterns, starting and finishing at Berkhamsted Cricket Club. Fully marked route with three full aid stations, around 800 m elevation and a 9 hour cutoff, limited to 350 runners.

Night trail running in Alice Holt Forest on 31 October 2026 with 5 km laps to make 5 km, 10 km or 15 km. The course is fully marked, has one outpost per lap and offers free parking and timed results.

An evening Halloween run at Hogmoor with 3.3K kids, 6.6K and 10K loop options plus a 6.6K canicross. The course has sandy hills, mud and shallow water; medals, free parking and onsite refreshments are provided, fancy dress and a torch are r..

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 beach run at West Wittering with 15.3k, 10k and 5k options along Blue Flag sands, chip timing, water stations and a finisher medal, plus course signage and first aid cover.

An off road ultramarathon from Maiden Newton of about 35.9 miles with roughly 1,300 m of ascent, passing hillforts and coastal views. Six aid stations offer water and cake, GPX files and maps are provided for navigation.

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.

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.

Trail races from Goodwood Racecourse into the South Downs National Park offering 12k, 16.5k and 21.3k distances with mixed forest roads, bridleways and single-track trails. Canicross options available and entries include chip timing and a f..

Night trail running at Stonor Park on 7 November 2026 with three marked routes of 17 km, 13 km and 7 km. Middle and long routes include an outpost and the event offers timing, parking and on site facilities.

Experience a scenic trail run through the Bedfordshire countryside starting from Leighton Buzzard. Choose between a classic half marathon or a metric distance featuring canal towpaths, woods, and rolling hills.

Experience a twilight trail run through the historic landscape of Cranborne Chase. This 10 km off road course navigates through woods and parks starting from the grounds of Eastbury House.

A trail running event at Stonor Park on 7 November 2026 with three waymarked routes through the Chilterns AONB. Routes include steep sections up to 22 percent, outposts on the Middle and Half Marathon, and free parking at the venue.