Trail Running calendar near Ventnor 2026-2027

Join Esher Street O, part of the Winter Street O Series by Mole Valley Orienteering Club, at The Wheatsheaf in Esher. Choose a 60 or 40 minute score course with MapRun and relax with food and after the race refreshments at the pub.

Join the STAR Backyard Holmbury St Mary three hour trail challenge on 23 January 2026 and see how many 5 km laps you can complete around Holmbury Hill. A headtorch is required and entry includes a warm bowl of chilli or curry.

Brutal @ Bagshot serves up a muddy, hilly Army training circuit with bogs, twisting climbs and knee to waist deep water holes. The 10 km is two gruelling laps.

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.

Pick your distance on the day at Running Tribe Races in Chalfont St Peter and tackle looped trails through woods and footpaths. Distances from 7 km up to marathon and ultra are offered, with an aid station serving food and drinks.

The Stonehenge Stomp is a not timed walking event around Stonehenge with marked routes of 5 km, 10 km, 20 km, 30 km and 40 km and marshalled checkpoints. Fifty percent of proceeds support Salisbury Hospice Charity and entries are online onl..

Take on the Ashdown Forest 10 and 5 Mile on 25 January 2026 at Pippingford Park, a scenic trail run through rolling forest terrain with rewarding climbs and wide open views. Free parking, medals for all and cash prizes for podium finishers..

Choose a half marathon or 10K through Moors Valley woodlands with muddy trails, steep climbs and chances to spot deer and birds of prey. Finishers get a wooden medal and the course is fully supported and timed.

Take to flat, scenic trails through Alexandra Gardens beside Windsor Castle with chip timing and friendly post race goodies. Choose 10K or half marathon, enjoy well marked routes, free photos and an event village for food and drinks.

G3 no.2 brings a friendly winter race to Hound House Road, Surrey on Saturday 31 January 2026. Pick a 10 km or 15 km route and enjoy clear signage, field parking and a welcoming series atmosphere.

Starburster is a twilight 5 or 10 mile run through Hurn Forest on 31 January, with out and back laps on firm forest trails beneath sunset skies. Head torches are required and 20% of entry fees support Forestry England for trail care.

Join WRNL 12 in Corfe Mullen for a 60 minute street and park score orienteering event based around the Dorset Soldier pub. SI timing, free parking and pub food on site. Juniors enter free; bring high visibility clothing and a torch.

Guided 10 km trail run around the Devil's Punchbowl in Hindhead, with summer sunset runs and headtorch group night runs in darker months. Social pace, great views and the chance to try trail gear.

The Pilgrim Challenge will take place in Farnham from Saturday 7 February 2026 to Sunday 8 February 2026. You can run 66 miles.

Hibernal Hills opens the season with a single loop in Hampshire on runnable but undulating trails with some long climbs. Choose 50 mile, 50 km or 20 mile routes, waymarked with live tracking and chip timing.

Trail running at Amberley Museum in West Sussex with three waymarked routes on the South Downs Way. Distances range from 6 km to 22 km, with on course outposts, a reusable cup policy and free parking.

Run two scenic coastal half marathons in Portsmouth and Langstone Harbour over one weekend, enjoying harbour trails, seafront promenades and an optional ferry crossing. Complete both to claim the limited edition "Double Trouble" medal.

Drama Llama Run on the Thames towpath offers timed laps on a flat 5.3 km out and back course with a seven hour limit and a flexible start window. Pick 5 km to ultra and enjoy race support, same day results and a finisher medal.

Discover The Brails on Saturday 7 February with four colour orienteering courses catering from beginners to experienced navigators across scenic estate land near Hungerford and Marlborough. Entries are online only so book early and come pre..

Run the Portland Coastal Ultra Trail Marathon on 8 February 2026 around the island on the South West Coast Path, with marathon, half marathon and 10k entries. Enjoy dramatic coastal views, checkpoint support and chip timing on a self naviga..