Trail Running calendar near Maidenhead 2025-2026

Explore the Isle of Wight coastal path from Chale, passing the Needles, Cowes, Culver Down and Ventnor on distances from 10 miles to a 106 km island loop. Fully supported with checkpoints, timing and an optional two day camp for walkers, jo..

Take on the Thames Path 100, a scenic 100 mile point to point trail from Richmond to Oxford along mostly flat, fast riverside paths. With a 30 hour limit, aid stations and an iconic finish at Oxford University, this is a classic ultra.

Join a guided, non competitive 30 mile ultra around Surrey's North Downs and Greensand Way, tackling iconic climbs like Leith Hill and Box Hill. Ideal for first time ultra runners seeking scenic trails with experienced group support.

Join the Mid Sussex Marathon Weekend, a three day running series through East Grinstead, Haywards Heath and Burgess Hill with undulating multi terrain routes combining into a full marathon. Family friendly races welcome all abilities.

Run Silchester invites runners to scenic trail routes around Roman walls, past a 12th century church and through ancient woodland. Choose 2.5, 5 or 7 miles, collect a new medal and enjoy a community event supporting the local food pantry.

Discover the Cotswolds with Tempo Trail Races on 3 May 2026, offering scenic trail distances from 10K up to a new 50K and a 100 km ultra. Choose your challenge and soak up friendly club vibes and beautiful countryside.

Join the Rapid Relays at Culden Faw Estate for solo or team relays, 5K and 10K sunrise runs, plus downhill time trial challenges. Chip timed with live splits, scenic woodland trails and free parking make it perfect for teams and supporters.

Run the Three Forts Challenge on the scenic South Downs on 3 May 2026, following rolling chalk and flint trails with some technical sections and fantastic views. Choose marathon, half or 5 mile routes with strong marshal support and proceed..

Tackle Box Hill on a guided 12.5 mile trail run with about 1000 m of climbing through woodland, heathland and open fields. An experienced guide will lead a steady group pace for runners who can hold roughly 10 min per mile, with parking nea..

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..

BigWayRound Winchester is a scenic trail run around the Itchen, St Catherine's Hill and the South Downs, offering 14 mile to 50K distances. Timed chip results, fully marked course and a bespoke medal or choose a tree planting instead.

Harewood Forest Trail Race offers scenic spring running through undulating trails near Andover, organised by the Muddy Runners. Choose 5 km or 10 km for a fun, challenging forest outing for trail lovers.

Take on the Chiltern Hills 100K, a scenic trail ultra across iconic Chiltern ridges and estates on 9 May 2026. Limited field and UTMB Index status mean a competitive, well supported race with challenging climbs, full marking and live tracki..

Run to the Sea Brighton on Saturday 9 May 2026 is a scenic point to point 50k from Horsham to Hove Lawns, crossing trails, rolling downs and the coastal promenade. Enter by 25 April; solo and 2 runner relay options with on course support.

Run scenic off road trails through Collingbourne woods at the Collingbourne Races, with half marathon and 10 km options. Chip timed event with medals and prizes for a memorable trail day.

Spend a weekend at Deene Park for the Run Rabbit Trail Festival with 10k, scenic half marathon, a 25k made of five 5k loops and a Quest to complete all routes. Festival vibes, varied trails and medals for all finishers.

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..

Tackle 40 miles along the ancient Ridgeway from Avebury to Streatley on 9 May 2026, passing barrows, hill forts and the Uffington White Horse. Friendly checkpoints and great support make this a memorable long distance walk.

Run beside the Thames at Runnymede for the Magna Carta Summer with 10 km, half and full marathon options that pass historic riverside landmarks. All finishers receive a bespoke Magna Carta medal.

Join the 30th Halstead & Essex Marathon on scenic low traffic roads through rolling hills, woods and farmland. Limited to 500 runners, this club organised race offers a classic country marathon and a prize for course records.