Trail Running calendar near Chesham 2026-2027

Run a marathon or half marathon at Denbies Wine Estate on 20 June 2026, tackling a scenic off road loop through the vineyards. Choose attended or virtual entry, enjoy chip timing and a collectible community medal while places remain limited..

Run 1 mile each hour for 24 consecutive hours at Denbies Wine Estate in P24 The Longest Attended Day, an off road challenge for attended and virtual runners. On site camping and a hefty finisher medal await but places are limited.

Experience the beauty of the South Downs National Park with distances ranging from 30km to a 100km nonstop ultramarathon. Enjoy fully supported trails passing historic landmarks and stunning coastal vistas near Chichester Harbour.

A trail event on the Malvern Hills offering *27 miles* with about 5000 ft ascent or *15 miles* to Black Hill. Routes use tracks and paths, include staffed checkpoints with snacks, and finish at Colwall Village Hall.

Join the Phoenix Hydra 75 Mile Ultra at Denbies Wine Estate in Dorking for a scenic 1 mile off road loop with chip timing and a staffed aid station. Distances run from 12 hour to 100 miles and all entrants receive a free memento.

Run the Maldon Ultras on 20 and 21 June 2026 in Maldon, with 100 mile, 50 mile and 30 mile lapped races across fields, woodland and vineyards with estuary views. Small fields and scenic off road laps make for a friendly yet fierce ultra.

A 5K off-road trail run around Castle Bytham within the Midsummer Festival, running across Lincolnshire countryside with marshals. Dogs on short non-retractable leads are welcome and junior runners may take part with a registered accompanyi..

Experience the twilight beauty of Ardingly Reservoir during this midsummer evening run. Choose between a 5k or 10k distance on a scenic undulating trail featuring a fully stocked aid station and finisher medals for all.

Celebrate the longest day at the Summer Solstice Challenge around Abberton Reservoir, a timed loop with 5 km laps. Run as many laps as you like, earn a medal and support Essex Wildlife Trust.

A 21.2 km trail half marathon on the National Trust's Dunstable Downs on 21 June 2026, featuring 450 m of ascent, two on-route aid stations and fully marked trails with GPX support.

Run through the historic landscapes of Horsell Common where the Martians first landed in literature. This volunteer led charity event offers trail routes from 2 km to 21 km in a scenic Site of Special Scientific Interest.

A multi terrain 10 km run on 21 June 2026 at Twisted Tree Brewery in the private Tusmore Estate near Bicester. Two options include a Canicross 10 km and every finisher receives a medal plus a beer or non alcoholic drink and a pint cup.

Community running event in Hawkhurst on 21 June 2026 offering 10k, 5k and a free junior race on a multi terrain undulating course, with finish line cake, a bespoke medal and funds raised for local community projects.

Circular countryside routes of 26 miles and 18 miles around Baldock in Hertfordshire, with checkpoints, refreshments and a light finish meal. Entries close 13 June or when the 175 place limit is reached.

A trail running event set inside Trent Country Park, Enfield, with wooded paths, grassy sections and some hills. Races include a 10 km senior race, a 4.5 km junior race and a 2 km kids fun run.

A flat, timed 10 kilometre out-and-back from the toll bridge in Shoreham to Bramber and back on 21 June 2026, with a halfway aid station, full marshals, 4x4 pickup and a new medal; entries open 20 March.

A scenic off road 10 km trail at Panshanger Park with chip timing and a sustainable finisher medal; proceeds support local charities and a family fun run is included.

Experience an evening trail run at The Valley in Evesham featuring a two lap 10 km course through the country park. This pet friendly event offers a simple racing format with water stations and onsite facilities.

A trail event on 24 June 2026 around the Malvern Hills offering 10 km and 5 km routes on mixed off road and tarmac terrain, with finisher medals, prizes, a 2 hour cut-off and on-site parking and refreshments.

A twilight trail race at Ashburnham Place in Battle, East Sussex offering 10k, 5k and a junior run. The event supports four charities and features on-site charity tents, a BBQ and a free sports massage.