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Trail Running Calendar near Milford 2026-2027

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Explore the top trail runs near Milford for 2026-2027! We've gathered 276 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

May 2027
Trail run around Winchester offering 14 mile, 19 mile, marathon and 50K distances on marked, chip timed courses with aid stations and parking options.
Two-day self supported navigation and endurance event for teams of two at Newlands Corner in the Surrey Hills, with basic camping, map based scoring and limited entries.
Point-to-point 50 km ultramarathon from Horsham to Brighton across trails and downs, with feed stations, GPS route, medical support and relay and team options.
An inflatable obstacle run in Stoke Park, Guildford on 8 May 2027 offering laps of 2.5 km with distances from 2.5k to 15k, music zones, on-course water and a finisher's medal.
A four month summer series at Dinton Pastures with 5km, 10km and a 2km kids race on flat traffic free lakeside trails, featuring medals, chip timing and on course marshals.
Obstacle-course weekend in Henley-on-Thames on May 15 and 16 2027 with Sprint 5 km, Super 10 km, Beast 21 km and kids races by the River Thames.
A 50 mile point to point trail race along the North Downs Way from Farnham to Knockholt Pound with 5,600 ft of climb and six fully stocked aid stations.
Looped event at Denbies Wine Estate offering distances from 5 km to ultra, run as many 5.3 km laps as desired within a 7 hour limit.
Race for Life in Winchester at North Walls Recreation Ground offers 3k and 5k routes on grass and tarmac with accessible facilities and a minimum fundraising target.
Looped trail event at Wiston Estate with a marked 10K circuit and distances from 10K to 100K, plus aid stations, a dedicated 100K area and on-site camping.
A weekend of waymarked trail runs and walks at Mapledurham House near Reading, featuring ultras, a half marathon and supported marathon-length walks.
A 7 km cross-country fun run at Trenchmore Farm on 22 May 2027 with music, burgers and a free drink for each runner.
A single-lap 50 km multi-terrain ultra in Maidenhead along the Thames Path and Jubilee River with four aid stations, chip timing, live tracking and race photos.
Point-to-point trail event in Surrey offering 62K, 41K, 20K and relay options with chip timing, marked routes, aid stations and free race photos.
Stand & Deliver challenges runners to repeat a scenic 4.2-mile loop at The Dell in 12-hour, 6-hour or Backyard formats, with solo, pairs and teams of three options.
A 5 km obstacle event at War Memorial Park on 23 May 2027 where participants climb, crawl and slide across mixed grass and path terrain; entrants must be 13 or older and a minimum fundraising target of £50 applies.
Guided 13 miles through the Surrey Hills from Guildford, run as a steady group with trail sections, car parking and nearby train access.
Trail challenge from Richmond upon Thames to Brighton with 100 km, half and quarter distances, GPS tracking, staffed rest stops, camping and shuttle transfers.
A family-friendly Colour Challenge at Henfold Lakes on 29 May 2027, based on the Nuts Challenge course with obstacles adapted for broad participation; tickets are sold out.
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