Trail Running calendar near Maidenhead 2025-2026

Blindfolded and dropped at an unknown location, The Drop in Winchester challenges solo runners and teams to find their way back over 10 or 15 miles as the crow flies. No maps or GPS allowed, just navigation, grit and a taste for adventure.

The Ale Trail 15 mile run is a pub-led trail race in Alfriston, East Sussex, starting from the Ye Olde Smugglers Inne beer garden. The 15-mile course has a 4hr30min cut-off and pub checkpoints at The Hampden Arms and The Ram Inn, where runn..

Event overview The Chase Trail Run 2026 is part of the Garmin UK Trail Running Festival on 26th April 2026. The event takes place at St Giles House, Wimborne St Giles, BH21 5NA and is organised by ORA Events Limited. Entries close on 22nd A..

Take part in The Other Run in Bury St Edmunds on 26 April 2026 with 5k, 10k, half and marathon options on scenic country roads. Enjoy a bespoke finisher medal, friendly atmosphere and a seven hour marathon cutoff.

Run a flat, fast 5K or 10K along the River Adur and Downs Link at Adur Recreation Ground in Shoreham by Sea, passing the airfield and Toll Bridge. Chip timing and finishers medals add to this well supported riverside race.

Tackle the Coventry Way Challenge, a scenic 41.4 mile loop through Warwickshire and Solihull on mainly off road trails. Solo runners and relay teams of up to six enjoy staffed checkpoints, food stops and a hot meal at the finish.

Join an 8 hour timed challenge around the scenic Eastnor Castle estate, solo or in relay, with views of the castle and Iron Age British Camp. Go for distance targets up to 50 miles and note headtorches are required for the final hours.

Saturn’s Midweek Chasing Numbers 7-Hour Time Challenge is held at Wraysbury Skiff & Punting Club on the River Thames. The event is designed to be affordable and flexible, inviting all abilities to run or walk within a 7-hour window. Partici..

Enjoy a three day running festival over the May Bank Holiday across three Mid Sussex towns. Run single town races or combine stages into the Mid Sussex Marathon, with undulating multi terrain routes, medals, family fun and fancy dress.

Join Run Silchester on 2 May 2026 for 2.5, 5 and 7 mile trail runs around the Roman wall, ancient woodland and a 12th century church. Family friendly festival atmosphere with stalls, music and proceeds supporting local community causes.

Take on the iconic Thames Path 100 from Richmond to Oxford, 100 miles of scenic riverside trails and historic towns. Enjoy waymarked routes, plenty of aid stations and a supportive ultra atmosphere for a true point to point challenge.

Join a guided 30 mile trail run along the North Downs Way and Greensand Way led by an experienced ultra runner and coach in a supportive group run. Enjoy sweeping hilltop views, shoe demos and a possible alcohol free beer at the finish.

Experience the Isle of Wight Ultra Challenge from Chale, tracing dramatic coastal cliffs past the Needles, Cowes and Ventnor. Multiple distances, strong support and camping options welcome runners and walkers seeking a scenic big day or two..

Run a scenic woodland course at Culden Faw Estate on 3 May 2026 with solo, pair and team relays plus timed 5K, 10K and the Henley Downhill Time Trial. Expect gentle undulations, a climb before 3 km and a long downhill finish with chip timin..

Hit the Cotswolds trails with Tempo Trail Races on Sunday 3 May 2026, featuring distances from 10K up to a 100K ultra. Pick your challenge or try the new 50K option for a weekend of scenic, adventurous running.

The Bluebell Bash is a trail running event in Manswood, Wimborne, UK, organized by Tri-Counties Trail Running. It offers three distances—half marathon (13.1 miles), 10K, and 5K—with full accessibility for canicross. Runners traverse scenic..

Join a guided Box Hill Vertical KM group run near Dorking for a tough 12.5 mile route with about 1000 m of climb through woods, heath and open fields. Enjoy expert guidance, technical terrain and a social finish.

Take on the Three Forts Challenge across the South Downs with rolling hills and coastal views. Choose marathon, half marathon or 5 mile trail and even bring your dog, with net proceeds supporting local Sussex charities.

BigWayRound Winchester is a scenic trail run from 14 miles to a 50K ultramarathon across the South Downs and along the River Itchen, with chip timing and self seeded waves. Choose a finisher medal or plant a tree to celebrate your finish.

Enjoy spring trails at Harewood Forest in Hampshire with Muddy Runners, choosing from 5 km or 10 km routes across undulating woodland tracks. A friendly, scenic race perfect for trail newcomers and regulars alike.