Trail Running calendar near Upper Woolhampton 2025-2026

On 15 January 2026 the Angry Run invites runners to tackle an offroad looped course at Pengethley Manor, choosing distances from 5k to ultra. Expect rolling hills, vineyard trails and a friendly festival atmosphere.

Tackle the Gluttonous Run at Pengethley Manor, part of the 7 Deadly Sins series on 16 January 2026. Pick 5k to ultra and brave a tough off road loop through vineyards with a hill each lap, or opt for the virtual challenge.

The Greedy Run at Pengethley Manor on Saturday 17 January 2026 invites runners and walkers to choose from 5k up to Ultra on an offroad loop through vineyards and rolling hills. Race day has hot drinks, food, free parking and a finisher meda..

Maverick New Forest Gravel invites runners to explore scenic gravel trails and woodland mud on 6 km, 12 km or 22 km routes. Bring a reusable cup and you can run with your dog.

Take on the iconic Box Hill fell race on Sat 17 Jan 2026 from the Stepping Stones pub, a challenging 12 km route with 530 m of climb and sweeping Surrey views. Pre entry only and entries fill fast, so be ready when entries open.

Join the Tiaras & Tutus Orange Run on 17 January for distances from 5 km to ultra along a flat riverside towpath. Enjoy a flexible one hour start window, seven hour time limit and bespoke finisher medals in a fun, limited field event.

Run the South Downs Way from Heyshott to Arundel Lido on 18 January 2026, choosing either a marathon or a scenic 15 Mile route. Expect muddy winter trails, river views and a friendly finish with coach transfer back to the start.

Take on the Riverbank Rollick a scenic 9.6 mile off road trail run along riverside paths, through woodland and a stream crossing. Earn a metal finisher medal that links to two other Thornbury Running Club races for a collectable series.

Tackle the Envious Run on 18 January 2026 at Pengethley Manor, a scenic offroad loop through vineyards with a hill each lap. Choose any distance from 5k to ultra or run virtually in January for a finishers medal.

Ryde Harriers host a three race cross country series at Smallbrook Stadium on 18 January, 15 February and 22 February 2026. Open to ages 15 plus with just 300 places, pre entry is recommended and runners should bring cross country spikes or..

Tackle the scenic but testing Benfleet 15, a 15 mile trail taking in Hadleigh Downs, the Canvey sea wall and parts of the 2012 Olympic mountain bike course. Join the fun at Hadleigh Country Park on 18 January 2026 for a muddy, memorable cha..

Join The Dirt Run, a two round multi terrain series in Northamptonshire with trails, paths and a muddy hill to conquer. Choose 5 km to 15 km routes and collect a custom finisher medal amid scenic parkland.

Join the Red Robin Run at Southwater Park on Sunday 18 January 2026 for a timed, flat trail challenge on the Downs Link where you can choose 5k to ultra distances on the day. Enjoy a festive Red Robin finisher medal and limited places.

Night street orienteering in Chelmsford as part of the Essex Winter Midweek Series. Use MapRun or printed waterproof maps to tackle Long or Short courses through roads, paths and parks under torchlight for series points.

Take on a three hour trail challenge from Holmbury St Mary and complete as many 5 km laps as you can across scenic Surrey Hills trails and the climb to Holmbury Hill. Entry includes a bowl of chilli or curry and a headtorch is required.

Tackle a wet and hilly trail at Bagshot on Saturday 24 January 2026, with splashy puddles and twisting climbs to test you. Choose a single lap 5 km or two lap 10 km for a muddy, adventurous winter race.

Huffin Puffin Run on 24 Jan 2026 at Xcel SPORTS HUB, Walton on Thames. Flat 5.3 km riverside loop with distances from 5 km to ultra; lap as you like within the time limit and enjoy aid stations and digital results.

Running Tribe Races in Chalfont St Peter offer looped 7 km or 10 km courses with choices on the day from 7k up to ultras. Enjoy scenic trails through woodland, a staffed hub for support, and welcoming pacers.

Join the Stonehenge Stomp on 25 January 2026 for a scenic walking event that welcomes runners and is not a race. Choose routes from family friendly 5 km up to 40 km and enjoy stunning views of Stonehenge in a popular, limited entry event.

Tackle scenic trails through Ashdown Forest with 5 and 10 mile options on 25 January 2026 at Pippingford Park Manor. Expect rolling climbs, bespoke medals, podium cash prizes and free parking for a rewarding winter trail challenge.