Trail Running calendar near Penshurst 2026-2027

Join a guided 30 mile trail run near Guildford on 2 May 2026, following the Greensand Way and North Downs Way past Box Hill and Leith Hill. This non competitive group run includes route guidance, coaching and stunning Surrey views.

Run the Mid Sussex Marathon Weekend, a three day festival across East Grinstead, Haywards Heath and Burgess Hill with 10 mile races, a 10k and a combined full marathon. Expect varied, undulating routes and family friendly fun.

Run Silchester offers scenic trail races from the village playing field along the Roman Wall and through ancient woodland, with a 2.5 mile fun run plus 5 and 7 mile trail races. Enjoy festival vibes, medals and community fundraising for the..

Join the Rapid Relays at Culden Faw Estate for solo or team relays, 5K and 10K sunrise runs, plus downhill time trial challenges. Chip timed with live splits, scenic woodland trails and free parking make it perfect for teams and supporters.

Take on scenic trail routes across the South Downs with rolling hills and coastal views at the Three Forts Challenge in Lancing. Choose marathon, half marathon or 5 mile and support local charities while enjoying a welcoming community atmos..

Join a guided Box Hill trail run with about 1000 m of ascent over 12.5 miles, featuring steep technical climbs and short scrambles. Led by a qualified mountain leader, the steady paced group suits experienced trail runners.

BigWayRound Winchester is a scenic trail run around the Itchen, St Catherine's Hill and the South Downs, offering 14 mile to 50K distances. Timed chip results, fully marked course and a bespoke medal or choose a tree planting instead.

Join Muddy Runners for the Harewood Forest Trail Race, a spring 5k and 10k through undulating woodland trails near Andover. Scheduled for 4 May 2026, this scenic, muddy course is perfect for adventurous runners; registration opens soon.

Take on the Freddo Mercury Rhapsody Run along a flat riverside towpath at Xcel SPORTS HUB, logging as many 5.3 km laps as you can within a relaxed 7 hour limit. Rock up in a 1.5 hour start window or request a time, with aid stations and opt..

Take on the Chiltern Hills 100K, a scenic trail ultra across iconic Chiltern ridges and estates on 9 May 2026. Limited field and UTMB Index status mean a competitive, well supported race with challenging climbs, full marking and live tracki..

Run to the Sea Brighton on Saturday 9 May 2026 is a scenic point to point 50k from Horsham to Hove Lawns, crossing trails, rolling downs and the coastal promenade. Enter by 25 April; solo and 2 runner relay options with on course support.

Discover Goring Gap Trails near Reading in early May 2026, offering scenic trail challenges from a 6 mile walk with a river boat crossing to 52K and 50 mile ultras. Multi day camping adds a relaxed festival vibe for runners and walkers alik..

Run along the Thames Path at Runnymede for a scenic 10k, half marathon or marathon on 9 May 2026, with marshalled, well marked out and back laps and GPX support. All finishers earn a bespoke Magna Carta medal and top runners win prizes.

Enjoy a scenic marathon through North Essex rolling hills, woods and farmland on low traffic roads this May. Celebrate the race's 30th year with just 500 places available for an intimate, well organised running experience.

Join Zig Zag Marathon and Half Marathon in Bury St Edmunds on 10 May 2026 for scenic, mildly undulating on road routes through Suffolk countryside. Small field, aid stations and included parking make for a friendly, focused race day.

Run the Oliver Fisher 10k or 5k at Milton Creek Country Park on 10 May 2026 and help fund the Special Care Baby Trust supporting Medway neonatal unit. Enjoy scenic off road trails and a friendly community atmosphere.

Run through the rolling vineyards of Rathfinny Wine Estate on 10 May 2026 with 10.7 km and 21.4 km half marathon options. Enjoy off road trails, recycled slate medals and a carbon neutral event that supports the WOLO Foundation.

Take on the Greenway Challenge on 10 May 2026 in Letchworth Garden City, a scenic self guided 13 mile loop around the Garden City Greenway. Enjoy a wooden finisher medal, post run treats and help raise funds for GRIT.

Enjoy scenic trail races across the South Downs around Cocking, with 20k and 10k senior options plus junior 3k and 5k races. Chip timing, medals and a lively race village make this a friendly, well marshalled day out for runners of all ages..

Run the Chilterns 30, a scenic 30 km trail around Tring with rolling hills and about 500 m of ascent through woods and ridgelines. Limited to 50 places, the well supported event includes guides, checkpoints and a finisher medal.