Trail Running calendar near Winchester 2025-2026

Enjoy a guided 13 mile trail half marathon through the Surrey Hills, visiting St Martha's Hill and sections of the North Downs Way. This relaxed group run emphasizes scenery and camaraderie rather than competition.

Run looped trail and road courses in Chalfont St Peter, from 7k to full marathon and ultras, with aid station, pacers and big drop bag access. Open to runners and walkers 16+, this friendly event showcases scenic woodland trails.

Join Phoenix Running's Christmas Advent Run on 30 Nov 2025 in Walton on Thames for scenic 5.3 km riverside laps and flexible distances. Limited to 150 entrants, all runners receive a chocolate advent calendar and a memento.

Night orienteering in Brockenhurst: a 60 minute score event in the New Forest. Visit as many controls as you can for points using SIAC timing and waterproof maps, and bring high visibility clothing and lights for after dark navigation.

Winter on the Downs offers single loop ultra races from Eastbourne over the iconic Seven Sisters cliffs, with 50K, 55 mile and 100 mile options. Expect winter trail conditions, dramatic coastal views and a true South Downs test.

Enjoy scenic trails across the South Downs from Plumpton Racecourse with 21.3 km, 12.0 km or 9 km options weaving tree lines, hilltop views and a flat finish. Chip timing, water stations and a finisher medal make it a rewarding day out.

Take on the dramatic Jurassic Coast path in Swanage with options from 10K to a 32 mile ultra on 6 December 2025. Expect challenging trails, full course marking and timing, and a finishers medal to celebrate your effort.

Join a magical evening run through parkland past the illuminated Cowdray Ruins at the Cowdray Winter Night Run. Head torches are mandatory and there are 5 km and 10 km distances plus dog friendly canicross and kids races.

Brave the winter trails of Salisbury Plain with undulating terrain, steep climbs and compact tracks across historic military land. Half and marathon options come with marked routes, aid stations and finisher medals, so bring trail shoes.

Explore the New Forest with Wessex Orienteering from Bolderwood Car Park, tackling technical woodland courses from a challenging Blue to a 60 minute Score challenge. Entry and parking are limited so book early and car share if you can.

Experience a magical night trail run through the atmospheric Cowdray Estate, passing the iconic ruins under the stars. Choose kids and adult distances from 3 km to 10 km for a fun evening in the Run the Seasons Winter series.

Support Hospice of St Francis at the Wild Christmas Charity Run, a guided 8km trail or 4km family walk from Church Farm Cafe. Enjoy a mince pie with entry, optional fancy dress and limited places so book early.

Run a scenic 50k through the Surrey Hills on a fully signed out and back trail with food stations and live timing. Friendly for newcomers to ultras yet rewarding for seasoned trail runners.

Join the New Forest Xmas Trails on 7 December 2025 for a festive run through heath and woodland in the New Forest. Fully marked single lap courses from 15km to 50km start at Holmesly Campsite and you can plant a tree instead of a medal.

The Mince Pie 10 is a festive 10 mile mixed terrain run in Peacehaven, with fancy dress, seasonal music and mince pies at the finish. Fun, muddy miles and a recycled medal await while supporting local children's and hospice charities.

Join the inaugural Allsorts Tinkley Gate Santa Dash for a festive family friendly 5 km trail run at Woodchester, with costumes and a post race cafe. Dress as Santa or an elf to support local charity Allsorts; dogs on short leashes welcome.

Join the Christmas Cracker at Newlands Corner on 7 December for pantomime themed family score orienteering and colour coded Orange Green and Blue courses. Guildford Orienteers will provide festive refreshments and friendly guidance.

Join the Phoenix Running Bobble Wobble Run at Crystal Palace Park for a timed multi lap challenge on park trails. Run as many 1.65 mile laps as you can in seven hours and collect a finishers medal and Phoenix bobble hat.

Take part in the festive Bobble Wobble Run at Ardingly Reservoir, choosing 5 km to ultra laps on scenic off road trails with a flexible start window. Finishers get the new double lined Phoenix bobble hat and a finisher medal unless you opt..

Join a lively 60 minute street and park orienteering score event around the Yachtsman pub, with SI timing and instant splits. Visit as many controls as you can to score points and test your map and pace skills.