Trail Running calendar near Chesham 2025-2026

Take on the Greenway Challenge in Letchworth Garden City: a self guided 13 mile clockwise run starting and finishing at Standalone Farm. Enjoy marshalled crossings, a wooden medal, and cake at the finish while supporting Headway Herts.

Take on the Midhurst Milers Cocking 10k, a hilly, scenic trail across the South Downs featuring steady climbs and a fast downhill finish. Limited online entries make this a must book for trail lovers chasing views and a rewarding run.

Join the Dilton Dash on 10 May 2026 at Dilton Marsh for a friendly community run supporting local causes. Choose 10K, 3K or a half kilometre fun run on scenic multi terrain paths, enjoy on site refreshments and a finisher medal.

Run the North Downs Way 50, a 50 mile point to point ultramarathon from Farnham to Knockholt Pound along iconic chalk ridge trails. Expect rugged terrain, big climbs and a 13 hour cut off for a true test of endurance.

Run the scenic Compton Downland Challenge on 16 May 2026, choosing 26.8 miles or 16 miles across the Berkshire Downs and parts of the Ridgeway. Expect rolling trails, friendly aid stations, a BBQ for finishers and a commemorative mug.

Join the Semington Slog on 16 May 2026 at St Georges School for 10k and 2k routes through the village and along the Kennet and Avon Canal towpath. Family friendly fun with marshalls, refreshments and a Slog Dog for every finisher.

Take on the Maverick Cotswolds Trail at Sudeley Castle and enjoy rolling trails, charming villages and historic views. Routes from 7 km to 50k, fully marked and timed with outposts and a finisher medal to celebrate your run.

The Reigate Priory Park 10K is a scenic charity fun run held in Priory Park, Reigate, Surrey. The course features a 250-meter start plus four laps on an accurately measured, gently undulating cross-country terrain surrounded by lush greener..

Explore Canterbury on foot at the Canterbury City Race European Tour from 22 to 24 May 2026. Three lively urban orienteering races send you through the medieval centre, cathedral quarter and university campus for a fast weekend of navigatio..

Run 50 km along the South Downs Way from Falmer to Beachy Head across rolling chalk downs, farm tracks and woods. Mostly runnable with 3,600 ft ascent, it finishes dramatically on the white cliffs for stunning coastal views.

Run from Richmond to Brighton over the North and South Downs on a scenic 100 km route to the coast. Choose single day or two day options with an overnight campsite, full support and GPS tracking.

Run the Grim Reaper Festival at Grimsthorpe Castle with distances from a 10 mile day or night race up to 100 miles, including a 100 mile team relay. Enjoy scenic 10 mile loops through woodland and lakeside trails, camping and medals for all..

Explore the Surrey countryside at The Fox, a trail running festival offering distances from 20K to 62K that all finish in Godalming. Enjoy scenic singletrack, regular aid stations and a friendly atmosphere on Saturday 23 May 2026.

Tackle the stunning Seven Sisters Half Marathon on the South Downs, a 13.5 mile single loop that crests the iconic cliffs, crosses Beachy Head and winds through Friston Forest. Expect rolling hills, mostly runnable trail and unforgettable c..

Take on the Grand Union Canal Race, a nonstop 145 mile ultra from Birmingham to Little Venice along scenic towpaths. Limited to 100 starters with a 45 hour limit, it welcomes supported and unsupported runners for a true canal challenge.

Join a scenic 26.2 mile marathon in Richmond Park over three laps of the Tamsin Trail and park perimeter. A 3 mile kids challenge follows, with on course drink stations and medical support for a safe, memorable morning.

Challenge yourself at Beat The Sunset 50 km on 30 May 2026 in Maidenhead, a scenic single lap mostly off road along the Thames Path, Jubilee River and Green Way. Expect chip timing, aid stations and a festive finish at the sports club.

Run the full 86 mile Ridgeway from Ivinghoe Beacon to Avebury Stones across sweeping chalk downland with a 28 hour time limit. Aid stations and navigation support make this a classic long distance trail challenge.

Take on the Three Castles 50 km ultramarathon along the scenic Medway Valley from Rochester to Tonbridge, finishing with a lap of the athletics track. Fully marked course with live timing and stocked aid stations for a memorable riverside c..

Castle Trails 30km, part of the Three Castles weekend, follows the River Medway from East Farleigh to Tonbridge. Mostly flat towpaths lead to a finale on an athletics track and a finisher medal within the 8 hour cut off.