Trail Running calendar near Windsor 2026-2027

The Phoenix Running - Brimscombe will take place in Brimscombe on Sunday 3 May 2026. You can run between 5 and 42 kilometers.

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..

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.

A 50 km point-to-point ultramarathon from Christ's Hospital, Horsham to Hove seafront, with trails, South Downs and a coastal finish. Options include an individual race and a 2-runner relay; course is fully signed and supported with feed st..

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.

A two-day trail running festival at Deene Park near Corby offering 10k, 21.1k, 25k challenges and a combined 56.1k Quest with medals and multi-event entry options.

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..

A linear 40 mile challenge from Avebury to Streatley along the ancient Ridgeway and chalk downlands of Wiltshire, Oxfordshire and Berkshire. Checkpoints provide refreshments and finishers receive an emailed certificate and badge.

A lapped riverside race from Wraysbury Skiff & Punting Club along the Thames Path near Runnymede. Offers 10 km, half marathon and marathon distances with marked turnarounds, marshals, a bespoke finisher medal and prizes for top three men an..

A marathon in May 2026 marking the 30th edition, organised by Halstead Road Runners on scenic low traffic roads around Halstead Leisure Centre in North Essex. Part of the Essex Road Running Championships with a strong volunteer and charity..

A circular multi-distance running event from Naseby Village Hall in Northamptonshire, featuring road and trail sections, GPS tracking and multiple checkpoints. The route direction alternates each year for a different course experience.

Road marathon and half marathon at Suffolk Running Centre near Bury St Edmunds, using the Kirtling and Windmill routes. Aid stations every 10 km, parking included, cupless policy, bespoke medals and a seven hour marathon cut off.

A fundraising off road 10 km, 5 km and junior run at Milton Creek Country Park on 10 May 2026, supporting the Oliver Fisher Special Care Baby Trust. The event features mapped trail routes, a bespoke medal, prizes and limited free parking.

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.

Take on the Greenway Challenge on 10 May 2026 in Letchworth Garden City, a scenic self guided 13 mile loop around the Garden City Greenway. Enjoy a wooden finisher medal, post run treats and help raise funds for GRIT.

Trail races of 20 km, 10 km and junior 3 km and 5 km run from Cocking Hilltop across the South Downs, with climbs, scenic views and marshalled, waymarked courses under Trail Running Association licence.

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.