Trail Running calendar near Haywards Heath 2026-2027

Run 50km along the River Medway from Rochester Castle to Tonbridge, passing three castles and scenic villages on flat trails. The race features a wave start, three aid stations, and a track finish, with a 9-hour cut-off. Your entry includes..

The Castle Trails 30km is a scenic point-to-point trail race along the River Medway from East Farleigh to Tonbridge. It offers a fully supported route with a flat, runnable profile and finishes with a lap on the track.

The Ridgeway Chase is a 60 km ultramarathon along the historic Ridgeway National Trail, starting at Ivinghoe Beacon and finishing near Wallingford. Held alongside a longer challenge, it offers runners scenic ridgeline views across the Chilt..

The Southampton Running Festival returns on May 31st, 2026. Runners can choose from 5K, 10K, or Half Marathon laps on a scenic route through Southampton Common. The event includes a lively village and support from marshals along the course.

This 50km ultramarathon is a unique point-to-point journey from Peckham, London, to East Peckham, Kent. Runners will experience a route that transitions from urban streets to the Kent countryside. The event offers aid stations and marked co..

Explore the scenic trails of the Surrey Hills on a guided half marathon. The route changes each time but always features iconic spots like St Martha's Hill. Choose from weekend runs or a special summer evening adventure.

The Sundowner Trail Marathon on 6 June 2026 is an evening 27 mile trail through saltmarsh, canal towpaths, vineyards and forests. Limited to 50 runners, this intimate race offers checkpoints, a finish memento and a bespoke local beer.

Run a 4.16-mile trail loop every hour until only one runner remains at this private farm venue in Hampshire. The event offers camping, full support, and a unique last-runner-standing format. It's a Bronze Ticket backyard ultra set on a vari..

Run laps through Denbies Wine Estate in the Fire Horse Run, a timed off road challenge on an undulating 5.3 km loop with distances from 5 km to ultra. Pick as many laps as you like within a seven hour window for a flexible, scenic race day.

Challenge yourself on the scenic forest trails of Wendover Woods. Choose from a hilly Half Marathon, 10k, or Junior Run. All finishers receive a bespoke medal.

Run on the sand at Bournemouth Beach. This event offers 5K and 10K distances, starting from Bournemouth Pier and heading east along the coast. It presents a unique challenge with its beach terrain and coastal views.

A lively fell race on Coombe Hill near Wendover on 7 June 2026, tackling 7 km with 220 m of climb and rewarding hilltop views. Entry on the day, modest fees and a pint included make this a friendly, competitive outing for juniors and teams.

Explore the testing trails of Alice Holt Forest in Surrey at the inaugural Wild Trail Runs. Choose between a 10km or Half Marathon distance, with chip timing and feed stations provided. Canicross runners are welcome, and all finishers recei..

Explore the coast of Thanet on this unique beach and trail run. The 10Bay Challenge offers two distances—a 15-mile or a 10k route—taking you across sands, promenades, and cliff tops during low tide.

A self-navigated 10k trail run celebrating an organizer's 20th anniversary. The route on public paths offers a mix of flat and hilly terrain. Finish with a commemorative vest and a well-earned drink at the Plough & Harrow.

Midweek summer evening trail race on Wednesday 10 June 2026 at Moors Valley Country Park in Ringwood. A one lap 10 km forest route with chip timing, aid stations and canicross options, presented with sustainable event measures.

A flexible 6-hour timed run along the flat, scenic Jubilee River near Slough. Run as many laps as you like on the 5.24-mile course, with everyone receiving a finisher's medal. The route offers countryside views and a riverside path.

The South Downs Way 100 is a 100-mile point-to-point race along the entire South Downs Way National Trail. Runners have 30 hours to cover the 85% trail course, supported by 12 aid stations. Finishers receive a buckle, with a special award f..

A 50km trail race on the iconic South Downs Way, fully within the national park. Starting at Matterley Bowl, it finishes at Queen Elizabeth Country Park with full support and a 9-hour cutoff. Part of the World Trail Majors - Short Series.

Trail runs circling the scenic Bewl Water reservoir in Kent. Choose from four distances, from 10km to a 50km ultra, on a mix of woodland paths and quiet lanes. The event features chip timing, stocked checkpoints, and finisher medals.