Trail Running calendar near Upper Woolhampton 2025-2026

Rapid Relays is a dynamic running event held at the scenic Culden Faw Estate in Fawley, near Henley on Thames, Oxfordshire. The race features a woodland trail course on estate tracks with gently undulating terrain, including a notable climb..

Discover the Cotswolds on foot at Tempo Trail Races 2026, a scenic weekend of trail racing on 3 May with distances from 10K to 100 km, and a new 50K option. Friendly atmosphere, challenging routes and stunning countryside await.

Tackle scenic South Downs trails at the Three Forts Challenge with full marathon, half marathon and five mile options calling at Chanctonbury Ring and Cissbury Ring. All profits support Ferring Country Centre and local charities.

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..

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.

BigWayRound - Winchester is an award-winning, Gold-rated trail running event held at Winchester Rugby Club. The event offers four distances: 14 miles, 19 miles, a marathon, and a 50K ultramarathon, catering to both new and experienced trail..

The Goring Gap Trails event, held in Mapledurham near Reading, offers a variety of running and walking challenges, including a 50-mile ultra, a 52K ultra, and a half marathon, alongside walking options of half marathon, full marathon, and a..

Run to the Sea Brighton is a scenic point to point 50k from the Sussex downs to Hove seafront with a two person relay. Expect trails, rolling hills, sea views, aid stations, medical support and a bespoke finisher medal.

The Collingbourne Races, held at Crawlboys Farm in Ludgershall, offer a scenic off-road running experience through the beautiful Collingbourne woods. Featuring a half marathon and a 10km race, the course includes bridle paths, woodland trac..

Join the Run Rabbit Trail Festival at scenic Deene Park for an inclusive multi distance trail running weekend with races and social events. Tackle short loops, a scenic half or go for the Quest for the Golden Carrot to earn extra bling.

The Chiltern Hills 100K is a scenic, challenging ultra around the Ridgeway, visiting Ivinghoe Beacon and Ashridge. Limited to 250 runners and UTMB World Series index race, this May event has rugged trails, great support and a Chesham finish..

Take on the Ridgeway 40 Walk on Saturday 9 May 2026, a 40 mile linear challenge from Avebury to Streatley across rolling chalk downlands. Enjoy sweeping views and pass Bronze Age burial mounds, Iron Age hill forts and Uffington White Horse.

Event overview The Rathfinny Run takes place at The Tasting Room, Rathfinny Wine Estate in Alfriston, Polegate (BN26 5TU) on 10 May 2026. The event is organised by 3WordRuns and is the third running of the race at this venue. There are two..

Take on the Midhurst Milers Cocking 10k Trail, a scenic but challenging 10k across the South Downs with a steady climb and a fast downhill finish. Licensed and chip timed with medals, prizes and a lively race village.

Take on the Greenway Challenge in Letchworth Garden City: a self guided 13 mile clockwise run starting and finishing at Standalone Farm. Enjoy marshalled crossings, a wooden medal, and cake at the finish while supporting Headway Herts.

Shires and Spires is a friendly multi distance loop from Naseby Village Hall offering races from 10 km to a 35 mile ultra across scenic trails and country roads. Routes alternate each year and GPS files plus live tracking guide runners.

Join the Hardy Half in Dorchester for scenic trail running with a 5 mile option or a challenging half marathon with about 1400 ft of climbing. Finish at Dorchester club where an event village, entertainment and local fundraising await.

Run the Compton Downland Challenge on 16 May in Berkshire with two scenic multi terrain routes across the Downs and Ridgeway. Pick the marathon or 16 mile route, expect muddy trails and finish in the village with a hand thrown mug.

Run the scenic 50 mile point to point North Downs Way from Farnham to Knockholt Pound on 16 May 2026. About 5,600 ft of climb, iconic climbs like Box Hill and fully stocked aid stations make for a rewarding supported endurance challenge.

The The Maverick Cotswolds Trail will take place in Cheltenham on Saturday 16 May 2026.