South East (England)
Trail Running Calendar South East (England) 2026-2027
Explore the best trail runs in South East (England) for 2026-2027! Our updated list features 346 exciting trail runs across the region. Find your next trail run in South East (England) below and join the trail community at these great events!
October 2026
Road and trail races in the Chiltern Hills on 11 October 2026 offering 5 km and 10 km routes with woodland paths, country lanes and notable climbs.
The Titsey Trail 10k is a community running event held on Sunday, 11th October 2026. Organized by runners for runners, it raises funds for a variety of local charities.
Trail and fun runs near Old Basing on 11 October 2026 with chip-timed 10K and 6K races plus a 2K family fun run supporting local schools.
Community organised 5k in Aldershot on 11 October 2026 with a flat course on the Polo Fields and Basingstoke Canal towpath, chip timing and finisher medals.
A 10 km undulating multi-terrain race from Buckingham Town Centre through Stowe National Trust gardens and countryside, with medals for finishers and local charities supported.
A lap-based out and back run along the Thames in Walton on Thames offering distances from a single 5.3 km lap up to ultra distances with a seven hour limit.
A lap based Friday timed run on a flat 5.3 km out and back course along the river Thames, with distances from 5 km up to ultra. Both attended and virtual entrants receive a finisher medal.
A 100 mile trail race from Goring & Streatley using Thames Path and Ridgeway, with 16 aid stations, a 28 hour cut-off and strict qualification and kit rules.
Annual 25 km and 50 km routed challenge across Kent, Surrey and Sussex with checkpointed support, food included and GPX route files provided.
Forest trail races at Bedgebury National Pinetum in October offering a half marathon, a 10K and a junior race with route maps, photos and limited free parking.
An off road cross country race of about 6 miles across Manor House Farm in Hardwick village with varied terrain and water crossings. Entries are limited to 300 runners and a minimum age of 17 applies.
A 10 km trail run through the private grounds of Hole Park, a historic estate near Cranbrook, Kent, on 18 October 2026. Entry is priced at £25 and the event includes timed results, finisher medals and official race photography.
A trail running event on 18 October 2026 from Fernhurst Recreation Ground to the Temple of the Winds on Blackdown, featuring a 10 km route with a 866 ft climb and an approximate 4.5 km alternative. Entries online only.
Trail runs of 10 km and 5 km around Blackpit Brewery on October 18 2026, using private multi terrain trails through woodlands and estate tracks. Entrants receive a medal, a pint cup and a free drink at the finish.
Timed multi-lap running at Buchan Country Park in Crawley with lap based distances from 5 km up to ultra, flexible start times and a seven hour time limit. Medal and lower cost no medal entry options are offered.
An approximately 8 km trail loop around Herstmonceux with over 70% trail, marked and marshalled, limited to 60 runners and featuring post-race tea and cake.
Beachy Head Marathon Weekend runs multiple trail distances from a 10k to an ultra near Bede's Prep School in BN20 7XL on 24/10/2026. Runners comment on clear signage, friendly marshals, stocked aid stations and hilly coastal terrain.
A point-to-point 47-mile ultra along the Thames Path from Iffley to Henley-on-Thames with five aid stations, mandatory kit requirements, and live GPS tracking.
A hip hop themed coastal run at Milford on Sea offering flexible distances from 5K to ultra and 5.3 km laps, with aid stations, a cupless policy, bag drop and a themed medal.
Trail marathon and half marathon near Canterbury through Kentish countryside; marathon requires navigation and both races use CCCU Sports Centre as HQ.