Trail Running calendar near Winchester 2026-2027

The Marlborough Downs Challenge offers two off road trail races across the North Wessex Downs, a 33 mile ultramarathon and a 20 mile trail. Routes visit Wansdyke, Avebury and other Wiltshire landmarks with notable elevation.

A guided 5 km spring trail run in the Chiltern Hills with a Movement Project session to improve range of motion. Groups are led by Run Leaders and the venue offers a cafe, toilets and bag storage.

Trail running festival around Winchester offering 14 mile, 19 mile, marathon and 50K ultramarathon routes on marked, marshalled trails with aid stations, bag drop and an option to plant a tree instead of a medal.

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..

An annual off road race at Hood Memorial Hall in Devauden on trails through Chepstow Park Woods, offering 10k, 5k, a 2.4k for ages eight and over, and a 60m junior dash with proceeds supporting local search and rescue.

A 100 km trail ultra on an anticlockwise loop of the Chiltern Hills, visiting Ashridge Estate, Whiteleaf and Bledlow Ridge. The fully marked course includes GPS tracking, six checkpoints, chip timing and post race food.

Run from Horsham to the Brighton seafront in this 50 km point-to-point ultramarathon. Choose the solo challenge or team up for a two-person relay across varied trails and coastal paths. The event offers full support with feed stations and t..

Enjoy scenic off road racing through Collingbourne woods with a chip timed half marathon or 10 km at Crawlboys Farm in Ludgershall on 9 May 2026. Marked trails, aid stations, medals and lively support make this a must for trail fans.

Experience a scenic 50 mile point to point ultra from Taunton to Minehead, starting on flat canal towpaths then rolling coastal trails past marshes, beaches and woodland. Enjoy aid stations, a medal and stunning Westcountry views.

Westcountry Ultra 100 is a scenic and tough 100 mile trail from Taunton to Minehead, following canals, rivers and coastal paths. Expect dramatic views, challenging climbs and a 32 hour cutoff with plentiful aid stations.

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..

The Ridgeway 40 offers a 40-mile journey along the ancient Ridgeway track from Avebury to Streatley. Traverse chalk downlands across three counties with support at checkpoints. Open to walkers and runners aged 14 and up.

Run along the historic Thames Path in Runnymede, near the site of the Magna Carta. This lapped course offers scenic views and multiple distances from a 10K to a full marathon. Every finisher earns a unique medal.

Run one or two loops through the undulating vineyards of Rathfinny Wine Estate on a carbon neutral trail event that supports the WOLO Foundation and awards recycled slate medals to finishers.

A self-guided 13-mile run along Letchworth's scenic Greenway trail. This is a run, not a race, due to road crossings. Finishers get a wooden medal and refreshments, with profits supporting a local youth mental health charity.

This scenic trail run in the South Downs offers 10k and 20k distances. The hilly route provides stunning views across the Cowdray and West Dean Estates. The event includes chip timing, a finisher's medal, and a race village with refreshment..

Trail races through Thomas Hardy countryside near Dorchester offering a roughly 5 mile option and an about 13.1 mile half marathon. Routes are mainly trail with steep sections and an event village at Dorchester Rugby Club.

Join the Dilton Dash on 10 May 2026 at Dilton Marsh for scenic multi terrain 10K, 3K and 1/2K fun runs supporting village causes. Expect stiles and gates, medals for all finishers and prizes for winners.

Explore the beautiful trails of the Chiltern Hills on this 30km guided trail run. The event includes a Run Leader, a checkpoint with snacks, and a finisher's medal. It starts near Tring Station, with easy rail access from London.

Tackle the scenic 10 km Scorpion Run at Symonds Yat Rock in the Forest of Dean with winding trails and a final climb to the finish. Enjoy undulating gravel tracks, riverside views and a cafe at the start and finish for post run treats.