Trail Running calendar near Princes Risborough 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.

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.

Challenge yourself at the Chilterns 30, a 30 km trail across scenic Chiltern Hills with rolling woodland trails, ridgelines and village paths. Guided groups, well stocked checkpoints and a finisher medal with a Trees not Tees certificate ma..

Join the Scorpion Run on 10 May 2026 at Symonds Yat Rock for a scenic 10k trail through the Forest of Dean and Wye Valley with riverside views. Expect gravel tracks and a tough final 1 km climb to the cafe finish with coffee and hot food.

Join Black to the Trails at Dunstable Downs and Whipsnade for a welcoming day of trail running with 1K, 5K, 10K and Scotch Bonnet 10K options. Celebrate diversity with music, food, family fun and finishers medals on scenic chalk downland.

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.

Take on the Compton Downland Challenge on 16 May 2026, choosing a scenic 26.8 mile marathon or a 16 mile route around the Berkshire Downs and ancient Ridgeway. Expect varied, sometimes muddy trails, great aid stations and a hand thrown 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.

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.

Join the Reigate Priory Park 10K on 17 May 2026 for a scenic cross country four lap route in Surrey. Enjoy a friendly race atmosphere, bespoke medals and the chance to support the charity Sport In Mind.

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.

Join the Deddington Four Farms Challenge on Sunday 17 May 2026 for 5k and 10k routes around the picturesque parish of Deddington. Open to experienced runners, fun runners and families, it is a friendly event supporting local charities.

Run from Richmond to Brighton on a scenic 100 km route through Surrey and the North and South Downs. Choose single day or two day options with Trailblazerz and Ultra March categories plus staffed aid stations and midway camping.

Run the Grim Reaper Festival at Grimsthorpe Castle Estate on May 23 and 24 2026, with options from 10 mile day and night loops to epic 100 mile challenges. Enjoy a scenic estate loop through woodland and along a lakeside railway and camp on..

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.

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.

Take on a scenic 26.2 mile marathon over three laps of Richmond Park, blending perimeter roads with the Tamsin Trail for varied, tree shaded running. Chip timing, marshals and aid stations ensure a well supported race day.

Discover Ealing on foot at the Queen of the Suburbs Ultra, a single borough trail event offering a scenic 50k ultra and a friendly 25k loop. Wind through parks, canal paths and Horsenden Hill for leafy views across west London.

Join the Rebellion 10km on Monday 25 May at Riverwoods, Marlow, for a scenic trail along the Thames including a crossing of Marlow Bridge. Finishers receive a medal, a Rebellion beer or non alcoholic alternative and a branded pint cup.