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Trail Running Calendar near Penshurst 2026-2027

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Explore the top trail runs near Penshurst for 2026-2027! We've gathered 143 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

May 2027
A supported trail event from Richmond to Brighton offering 100 km, 50 km, 25 km and marathon options with rest stops, GPS tracking, medical support and camping.
A single loop trail half marathon around the Seven Sisters and Beachy Head in the South Downs National Park, covering 13.5 miles with about 2,000 ft of ascent.
June 2027
A point-to-point 50 km trail race along the River Medway from Rochester to Tonbridge with a predominantly flat course, four aid stations and a 9 hour cut-off.
A point-to-point 30 km trail along the River Medway from East Farleigh to Tonbridge with three checkpoints, chip timing, bag transfer and an athletics track finish.
Two supported trail options in London - a 55 km ultra and a 25 km trail run along the Capital Ring, finishing at Richmond Green with feed stations and chip timing.
Community 3k and 5k runs at Dunorlan Park on mainly grass and woodland terrain with some inclines and limited general parking.
Trail half marathon from Chiddingly across the Wealdway and Vanguard Way, about 22.2 km with two checkpoints, chip timing, 5 hour limit and a 400 runner cap.
Urban 100 km ultramarathon in central London with 100 km, 50 km and 25 km routes that pass 100+ city landmarks and include staffed checkpoints.
A 75 mile off road ultra on a one mile loop at Denbies Wine Estate with up to 30 hours to finish, chip timing and multiple concurrent race options.
A 100 mile ultra on a flat one mile trail loop at Denbies Wine Estate offering 12 hour and 24 hour options plus 50, 75 and shorter races.
Trail marathon and half marathon at Denbies Wine Estate on 19 June 2027, run on a 1 mile loop with chip timing and an extended start window.
A 24 hour attended challenge at Denbies Wine Estate in Dorking where runners complete 1 mile on the hour for 24 consecutive hours; onsite tent camping, daytime cafe service and a simultaneous virtual option are provided.
A 50 mile loop ultra at Denbies Wine Estate in Dorking with a flatish one mile circuit, chip timing, several concurrent race options and up to 30 hours to finish.
Run one mile on the hour for 12 consecutive hours at Denbies Wine Estate with chip timing, a finisher medal, camping and a simultaneous virtual option.
Trail running in Surrey on 19 June 2027 with five routes from 5 km to 53 km through ancient woods and North Downs views.
Timed trail weekend at Leybourne Lakes with a fully marked 2.5 km loop and 6, 12 and 24 hour solo and relay options plus race village facilities and live timing.
Timed event at Denbies Wine Estate on 20 June 2027 using a 1 mile loop; runners choose distances from 1 mile to ultra and run laps within a six hour limit.
Community running event in Hawkhurst, Kent on 20 June 2027 offering 10 km, 5 km and a free junior run with finish-line cake, a free half pint and community fundraising.
Annual not for profit run organised by Istead & Ifield Harriers from Cyclopark through the Kent countryside with proceeds supporting local charities.
Trail races around Peacehaven through the South Downs, offering 10 km, a new 5 km and a chip timed Junior Mile with route maps and finish line medals.
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