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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 288 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2027
A late autumn half marathon in Richmond Park with a four-lap route through woodland and rolling hills, chip timing and free finish-line photos.
A commemorative 7 hour Time Challenge in Staines along the Thames with options from 3 km to ultramarathon distances and medals for finishers.
Trail half marathon and 10K at Wimbledon Common on 21 November 2027 with chip timing, free race photos and post race goodies.
Trail races through Alexandra Gardens with 10K and half marathon options, chip timing, free photos and support for Brain Research UK.
December 2027
Guided trail run at Box Hill covering 12.5 miles with about 1000 m of ascent across woodland and technical climbs, led at a steady group pace by an experienced guide.
A fully signed 50k trail ultra in the Surrey Hills from Dorking Sports Centre on 5 December 2027, with checkpoints, SportIdent timing and a 10 hour limit.
Riverside trail runs from Alexandra Gardens in Windsor offering 21.8 km and 15.7 km chip timed routes with a finisher medal and on course refreshments.
A four-lap half marathon in Richmond Park on 12 December 2027, run on mixed trail with chip timing, marshals, free photos and on-course aid stations.
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