Trail Running calendar near Greater London 2025-2026

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.

Five Rivers Ultra, 16 to 17 May 2026, is a point to point coastal ultramarathon that circles five estuaries between Suffolk and Essex, finishing in Harwich. Choose 100 mile, 50 mile or 50 km on mostly grass and dirt trails for flat fast run..

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.

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

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..

Run the scenic loop at Hurtwood Park Polo Club in Cranleigh, Surrey with distances from 5 km to ultra on mostly flat off road trails. Multi lap format and a seven hour time limit suit all paces and every finisher gets a memento.

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.

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..

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.

Run 60 km along the ancient Ridgeway from Ivinghoe Beacon to near Wallingford across chalk ridgelines and rolling downs. With 1000 m ascent, a 10 hour limit and UTMB World Series status, this scenic ultramarathon tests endurance and pace.

Run through Southampton Common on 31 May 2026 amid woodland, lakes and wetlands. Choose half, 10K, 5K or junior distances and enjoy a lively event village with food, freebies and a sustainable focus.

Enjoy a guided 13 mile trail half marathon through the Surrey Hills, visiting St Martha's Hill and sections of the North Downs Way. This relaxed group run emphasizes scenery and camaraderie rather than competition.