Trail Running calendar near Penshurst 2025-2026

Challenge the South Downs Way 100, a nonstop 100 miles along the chalk ridge from Winchester to Eastbourne with rolling hills, ancient forts and coastal views. Organised by Centurion Running, the race offers aid stations and a 30 hour limit..

Take on a stunning 50km trail ultramarathon along the South Downs chalk ridgeway, finishing at Queen Elizabeth Country Park. Expect rolling hills, wide views and solid on course support in this World Trail Majors stage.

Scenic off road trail running around Bewl Water in Kent, with forest paths, open countryside and lake views. Choose 10km, Half Marathon, Marathon or 50km Ultra, starting and finishing at the Visitor Centre with chip timing and checkpoints.

Run 14 miles across the dramatic South Downs on 14 June 2026, featuring a stiff climb, chalk descents and muddy slippery sections. Trail shoes recommended; enjoy water on course, post run cake and a commemorative truckers cap.

Tackle scenic but hilly forest trails at the Wendover Woods Half Marathon and 10k on 14 June 2026, with a friendly junior run and on the day entries if available. Spectators can enjoy a cafe, forest walks and family activities.

Take in sweeping views from Watership Down on scenic trails with marathon, half and 10K options. Enjoy chip timing, a finisher medal, goody bag and a keepsake beer glass while supporting Hampshire and Isle of Wight Air Ambulance.

Run through Hertfordshire countryside from 3 Brewers Brewery with 10 km and 5 km options over mostly off road trails, woodland and farm tracks. Finish with a medal, chip timing, a pint and live jazz for a festive post race vibe.

Run the Robertsbridge Midsummer 10k or 5k on 19 June 2026 at Robertsbridge Rec Ground, a friendly community race over a scenic undulating multi terrain course. Finishers get bespoke medals and can refuel with a BBQ and post race bar.

Beyond London on 20 June 2026 offers scenic trail runs through parks, woodlands and canal paths, finishing in Richmond. Choose 55 km from Woolwich or 25 km from Upper Norwood, with signed routes, GPX files, aid stations and a finisher medal..

Run a scenic point to point trail through Buckinghamshire, Bedfordshire and Northamptonshire with a 50 mile ultra or a marathon, both finishing at Marlow Park, Grafham Water. Waymarked routes, aid stations and medals for all finishers.

Centaur 100 Mile Ultra at Denbies Wine Estate invites runners from half marathon to 100 miles on a single off road 1 mile vineyard loop. Chip timing, stocked aid and a 30 hour limit for 100 miles make it a scenic buckle or medal chase.

Run a marathon or half at scenic Denbies Wine Estate, tackling a compact looped trail through vineyards with flexible start times and full chip timing. Enjoy a relaxed vibe and a Phoenix Running Community medal.

Race to the King on 20 June 2026 invites runners to explore the South Downs and Monarch's Way at West Dean Gardens, with coastal and castle views. Distances from 30 to 100 km include full support, food stops and a hot finish meal.

Take on the Dunstable Downs Half Marathon, a scenic 21.2 km trail with steep climbs and panoramic countryside views. Limited to 300 runners, this rugged UTMB World Series qualifier promises a memorable off road challenge.

The Midsummer Munro will take place in Walton on the Hill on Sunday 21 June 2026. You can run 13 miles.

Run the Martian Race at Horsell Common on 21 June 2026 and follow routes through the sandpits immortalised in H.G. Wells The War of the Worlds. Volunteer organised and charity focused, with distances for all ages.

Celebrate the season finale at Cowdray Estate with scenic routes across polo lawns, Ambersham Common and views of the Cowdray Ruins and South Downs. Canicross options, a kids run and post race BBQ and bar make for a festive family finish.

Tackle a full marathon over three days at the Colworth Marathon Challenge on the scenic Colworth Estate. Choose one, two or all three races and enjoy free camping, family entertainment and children's races for a festival feel.

Take on farm trail laps at Hyde Hall Farm with distances from 5k to ultra, including a Heavy Half option. On site parking and a bespoke finisher medal make for a friendly, flexible event.

Enjoy scenic Thames Valley trails at Marlow Rugby Club with 5K, 10K and Half Marathon options on well marked off road courses. Chip timing, free race photos and a themed finisher medal make this a fun, sustainable event for all abilities.