Trail Running calendar near Rochester 2026-2027

Experience a scenic 10 km trail run through the vineyards of the Rathfinny Wine Estate. Support a local cancer charity while enjoying hilly routes and beautiful views of the South Downs National Park.

Winter X is a mid-winter trail-running event in the Meon Valley offering 10, 30, 50 and 70 km on marked public trails with checkpoints and post-event food. Entries for 2025 are closed; a provisional date for 2026 is 28 December 2026.

Winter Runderland in Walton on Thames is a timed lap event on a 5.3 km riverside towpath course. Runners may select distances from 5 km up to ultra, and a lower-cost no-medal entry option is available.

Experience a historic trail race at Box Hill featuring significant elevation and panoramic views of the North Downs. This event offers a 10 km course on rough tracks with dedicated categories for men, women, and children.

Experience a winter trail adventure at the Penshurst Village Cross Country Run. Participants can choose between a standard five mile cross country course or a five mile cani cross run through scenic local landscapes.

Experience an iconic 43 mile ultra marathon journeying from the Buckinghamshire countryside to the heart of London. This season opener features scenic trails and historic canal paths with full GPS tracking and checkpoint support.

The Doughnut Dash is a flexible-distance run along a flat Thames riverside trail. Participants can run from a single lap to ultra marathon distances while enjoying doughnuts. All finishers receive a custom, neon-colored medal.

Run as many laps as you choose through the scenic gravel paths of Thetford Forest in this flexible 4 or 6 hour challenge event at Brandon Country Park.

Choose your distance from 5k to Ultra on this scenic road course near Bury St Edmunds. Enjoy a rolling route through historic villages with aid stations and a bespoke finisher medal.

A 15 mile multi-terrain trail run at Hadleigh Country Park featuring muddy, undulating sections and elevated Thames Estuary views. Route maps and GPX files are available and the event operates a cupless water policy.

Experience a rewarding trail race through the private grounds of Ashdown Forest with 1568 feet of elevation. Choose between 5 or 10 miles of hard packed trails featuring steep climbs and panoramic views across The Downs.

Experience a 53 mile winter trail loop through the South Downs National Park featuring 6400 feet of elevation. This fully marked UTMB Index race offers a scenic route along ancient ways and includes live GPS tracking.

Follow in the footsteps of ancient pilgrims on this 66 mile two day ultra adventure along the historic North Downs Way. Experience a supported winter trail challenge with overnight accommodation and full logistics included.

Discover scenic forest trails at the Bedgebury Forest 10 and 5 Mile in Kent. This undulating multi terrain event features distances for adults and a junior run under majestic pine trees.

Follow an ancient Roman road through Suffolk and Norfolk on this 48 mile ultra marathon. Run from a nature reserve to the coast on a well marked and relatively flat historical trail.

Celebrate nine years of running on the historic Flitch Way with various distances from 5km to a 6 hour challenge. Choose your direction on this flexible lapped course and select your favorite bespoke medal.

Experience a fully signed 50k trail ultra along the scenic North Downs Way and ancient woodlands of Norbury Park. Starting near Dorking this accessible route features four well stocked checkpoints and a finisher medal.

Experience a scenic run through Thetford Forest with distances ranging from 5km to an Ultra Marathon. Enjoy a loop-based course on forest pathways with post-race refreshments and bespoke medals at High Lodge.

Follow a historic 42 mile pilgrimage route through the scenic Essex countryside to an ancient coastal chapel. This challenging trail ultra features varied terrain and requires self navigation through rolling rural landscapes.

A 10 km multi terrain race from Windsor & Eton Brewery along Baths Island and Thames towpaths. The course is about half off road and the finish includes a pint cup and a free drink.