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Trail Running Calendar near Gerrards Cross 2026-2027

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Explore the top trail runs near Gerrards Cross for 2026-2027! We've gathered 271 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

December 2026
Essex Vets XC Championships in Epping Forest on 12 December 2026 features a single 8km course with veteran races and an £8 entry fee.
An offroad multi-lap event at Shalford Park, Guildford offering runs from 3.14 to 31.4 miles, a Pi marathon option, a 1-mile kids run, and bespoke Pi Pie medals.
A 26.2 mile marathon run entirely inside the Croydon IKEA store over multiple laps, with a strict six hour cut off, Swedish themed aid station and limited entry.
A December edition of the Second Sunday 5, a two lap informal run at Richardson Evans Memorial Fields on Wimbledon Common organised by Thames Hare & Hounds.
A festive, untimed fun run at Denbies Wine Estate with Santa suits provided, a 5 km mixed-surface route, charity support and post-run mulled wine and mince pie.
Join a festive Christmas run along the flat Jubilee River. Choose your own distance in this 6-hour timed event on a scenic towpath. All finishers receive a bespoke festive medal.
A dawn-to-dusk winter trail challenge at Box Hill, Dorking featuring a 10.1 mile loop with 2,400 ft climb per lap and on-course support.
Trail runs at Wendover Woods in the Chilterns offering a family Santa Mile plus 5 and 10 mile races with chip timing, medals, and finishers refreshments.
A 10 km trail run on the Yattendon Estate at Renegade Brewery on December 24th, with a Canicross category, medal, pint cup and a mince pie for finishers.
A 7 hour Time Challenge along the River Thames in Staines offering distances from 3 km up to 50 km, medal and goody bag, plus an optional Christmas dinner at The Last Hop.
A seven hour Time Challenge on a signed Thames riverside loop where participants choose their distance and select a past event medal on finishing.
A looped trail event in Crystal Palace Park where runners complete 2.65 km laps within a 7 hour time limit. Distances range from 5 km to ultra and all participants receive a finishers' medal.
A 10 mile cross country race in Hainault Forest over three laps on tracks and grassland, with on-the-day entries, a two hour cut-off and prizes for men, women and veterans.
A low key multi-lap half and full marathon along the River Thames in Walton on Thames on 28 December 2026. The UKA certified flat towpath course awards medals to all finishers and has limited places.
Trail event at Butlers Lands Farm with water crossings, Roman Walls and fields, offering 10K and 10 Mile options plus finish line mulled wine and mince pies.
January 2027
A single-distance trail race of 10.000 km on Box Hill with substantial climb, rough terrain, a concurrent children's run, a bag drop and a water station at 6 km.
A guided winter trail run of 10 km through Chilterns woodlands and hills, based at Church Farm Cafe in Aldbury with on site parking and bag drop.
A long-running off-road and road race on Epsom Downs offering 10 mile and 10k options while raising funds for local charities.
A riverside 3.28 miles out-and-back event at Wraysbury offering distances from 5K to ultra and a six hour challenge, licensed by TRA and run under UKA rules.
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