Trail Running Calendar South East (England) 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.

Join KNC9 at Maidstone East for a lively night street orienteering event using MapRun. Explore the town in a 60 minute score format chasing 30 controls, then unwind with fellow orienteers at the Newnham Court Inn.

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.

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.

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.

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.

Run a scenic 10 km loop around Rye Harbour Nature Reserve on 7 December 2025, mostly on trail and fully marshalled and marked. Limited to 70 runners, with postrace tea and cake at Winchelsea Beach Community Centre.

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.

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..

Winter Downs 200 is a continuous 200 mile trail loop around the South of England, featuring huge climbs and a 96 hour cutoff. Limited to 100 starters, this winter ultramarathon rewards navigation, resilience and winter grit.

Get festive at the Christmas Jumper Friday Run on a flat, scenic out and back beside the Thames, with distances from 5 km to ultra and a flexible one hour start window. Enter early to secure a free technical running top or take home a medal..

Join the Hampshire Christmas Advent Calendar Run in Forest of Bere for timed laps on a 5.3 km off road loop; start within a one hour window and run as many laps as you can in seven hours. All entrants get a commemorative medal.

Celebrate Pi at the Mince Pi Run in Shalford Park on 14 Dec 2025 with distances from a family friendly one mile Pi fun run to multi lap challenges and a Pi marathon. Enjoy waterside trails, bespoke Pi pie medals and only 200 places.