Upper Woolhampton

Trail Running Calendar near Upper Woolhampton 2026-2027

Explore the top trail runs near Upper Woolhampton for 2026-2027! We've gathered 130 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026

Run to Wine x Greyfriars Vineyard

Puttenham | 25 mi from Upper Woolhampton

Trail Run 8 km

A social 8 km trail run on the North Downs from Greyfriars Vineyard, finishing with lunch, a glass of English sparkling wine and a guided wine tasting.

A social 8 km trail run on the North Downs from Greyfriars Vineyard, finishing with lunch, a glass of English sparkling wine and a guided wine tasting.

The Maverick Hampshire Dark Gravel

Farnham | 21 mi from Upper Woolhampton

Trail Run 5 km 10 km 15 km

Night trail laps in Alice Holt Forest on 5 km circuits with 5 km, 10 km or 15 km options, one outpost per lap, free parking and no dogs allowed.

Night trail laps in Alice Holt Forest on 5 km circuits with 5 km, 10 km or 15 km options, one outpost per lap, free parking and no dogs allowed.

Brutal - Halloween @ Hogmoor

Bordon | 24 mi from Upper Woolhampton

Trail Run 7 km 10 km

An evening Halloween run at Hogmoor with kids, canicross, 6.6 km and 10 km options, fancy dress encouraged, medals for finishers and on‑site refreshments.

An evening Halloween run at Hogmoor with kids, canicross, 6.6 km and 10 km options, fancy dress encouraged, medals for finishers and on‑site refreshments.

Phoenix Running - Hampshire

Hampshire | 25 mi from Upper Woolhampton

Road Race Backyard Ultra 3 mi Half Marathon Marathon

A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.

A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.

November 2026

The Maverick Dark Oxfordshire Trail

Stonor | 16 mi from Upper Woolhampton

Trail Run 7 km 13 km 17 km

Night trail running at Stonor Park with three route distances, outposts on middle and long courses, no dogs and a cup-free outpost policy.

Night trail running at Stonor Park with three route distances, outposts on middle and long courses, no dogs and a cup-free outpost policy.

The Maverick Oxfordshire Trail

Stonor | 16 mi from Upper Woolhampton

Trail Run 7 km 13 km 22 km

Three trail distances through Stonor Park and the Chilterns with marked courses, fuel outposts, on site facilities and notable gradients.

Three trail distances through Stonor Park and the Chilterns with marked courses, fuel outposts, on site facilities and notable gradients.

Big Night Out Winchester

Winchester | 25 mi from Upper Woolhampton

Trail Run 12 km 22 km

A torchlit trail run from Winchester Athletics Track with 12 km and 22 km options across the South Downs Way and local trails. The course is fully marked; headtorches and at least 500 ml of fluid are required.

A torchlit trail run from Winchester Athletics Track with 12 km and 22 km options across the South Downs Way and local trails. The course is fully marked; headtorches and at least 500 ml of fluid are required.

Race to Remember - Aldershot

Aldershot | 21 mi from Upper Woolhampton

Trail Run 36 km 76 km

A fundraising running and walking challenge on 7 November 2026 offering 76 km from Aldershot or 36 km from Petersfield, finishing in the Historic Dockyard Portsmouth.

A fundraising running and walking challenge on 7 November 2026 offering 76 km from Aldershot or 36 km from Petersfield, finishing in the Historic Dockyard Portsmouth.

Windsor Trail Run Half Marathon

Windsor | 24 mi from Upper Woolhampton

Trail Run 10 km Half Marathon

A trail event in Windsor on 8 November 2026 offering a 10K and a half marathon on flat off road trails from Alexandra Gardens. The event features chip timing, race photos, post race goodies and an event village.

A trail event in Windsor on 8 November 2026 offering a 10K and a half marathon on flat off road trails from Alexandra Gardens. The event features chip timing, race photos, post race goodies and an event village.

Saturn Running - Egham

Egham | 26 mi from Upper Woolhampton

Road Race Trail Run 3 km 5 km ... Marathon 50 km

A licensed 7 hour Time Challenge in Staines along the River Thames with multiple distances from 3 km to 50 km, commemorative medals and distance pins.

A licensed 7 hour Time Challenge in Staines along the River Thames with multiple distances from 3 km to 50 km, commemorative medals and distance pins.

SATURN - Remembrance Run - South

Egham | 26 mi from Upper Woolhampton

Trail Run 3 km 5 km ... Marathon 50 km

Remembrance Run in Surrey along the River Thames: a 7 hour time challenge with distances from 3 km to 50 km, medals, aid stations, and a two minute silence.

Remembrance Run in Surrey along the River Thames: a 7 hour time challenge with distances from 3 km to 50 km, medals, aid stations, and a two minute silence.

Phoenix Running - Hampshire

Hampshire | 25 mi from Upper Woolhampton

Road Race Backyard Ultra 3 mi 13 mi 26 mi 29 mi

Timed multi lap event on the Itchen Way in Winchester on 14 November 2026, with 2.62 mile laps that add up to half marathon, marathon and ultra distances. Flexible start format, aid station with vegan options, bespoke finisher's medal.

Timed multi lap event on the Itchen Way in Winchester on 14 November 2026, with 2.62 mile laps that add up to half marathon, marathon and ultra distances. Flexible start format, aid station with vegan options, bespoke finisher's medal.

Rugged Radnage

Radnage | 22 mi from Upper Woolhampton

Trail Run 5 km 10 km

A multi-terrain 5K and 10K race in the Chiltern Hills on 15 November 2026, organised by the Radnage Primary School PTA, with water stations, first aid, a village hall cafe and proceeds supporting the school.

A multi-terrain 5K and 10K race in the Chiltern Hills on 15 November 2026, organised by the Radnage Primary School PTA, with water stations, first aid, a village hall cafe and proceeds supporting the school.

Saturn Running - Egham

Egham | 26 mi from Upper Woolhampton

Road Race Trail Run 3 km 5 km ... Marathon 50 km

A 7-hour time challenge along the River Thames with distances from 3 km to 50 km, themed medals, aid stations and parking in Staines.

A 7-hour time challenge along the River Thames with distances from 3 km to 50 km, themed medals, aid stations and parking in Staines.

Avebury8 Nine

Avebury | 29 mi from Upper Woolhampton

Trail Run 9 mi

Experience a 9 mile trail race through the Wiltshire countryside featuring neolithic sites and muddy tracks with all profits supporting the local Air Ambulance.

Experience a 9 mile trail race through the Wiltshire countryside featuring neolithic sites and muddy tracks with all profits supporting the local Air Ambulance.

Thames Path Trail Run

Windsor | 24 mi from Upper Woolhampton

Trail Run 16 km 22 km

Riverside trail run from Alexandra Gardens in Windsor with two distance options, chip timing, on-course support and a finisher medal.

Riverside trail run from Alexandra Gardens in Windsor with two distance options, chip timing, on-course support and a finisher medal.

Brutal @ Spider Hill

Aldershot | 21 mi from Upper Woolhampton

Obstacle Run 5 km 10 km

Mud- and water-filled trail laps at Spider Hill with 5 km and 10 km options across marshes, swamps and steep climbs.

Mud- and water-filled trail laps at Spider Hill with 5 km and 10 km options across marshes, swamps and steep climbs.

Devil's Punchbowl 10km

Hindhead | 28 mi from Upper Woolhampton

Trail Run 10 km

Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.

Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.

The Wallop

Farleigh Wallop | 13 mi from Upper Woolhampton

Trail Run Half Marathon

A timed 21k trail run across the private Farleigh Wallop Estate with cupless water stations, medics, parking included and a bespoke sustainable finisher medal.

A timed 21k trail run across the private Farleigh Wallop Estate with cupless water stations, medics, parking included and a bespoke sustainable finisher medal.

Silent Disco Run - Oxford

Cowley | 23 mi from Upper Woolhampton

Urban Trail

A community silent disco run at Rose Hill Community Centre on 28 November 2026 with a group warm up, headphones for music, glow items, post-run music, raffle and on-site refreshments.

A community silent disco run at Rose Hill Community Centre on 28 November 2026 with a group warm up, headphones for music, glow items, post-run music, raffle and on-site refreshments.