Trail Running calendar near Haywards Heath 2026-2027

A flexible 6-hour timed run along the flat Jubilee River towpath. Run one 5.24-mile lap or see how many you can complete. The scenic route passes through countryside with views towards Windsor Castle.

A trail event on 10 October 2026 near Maidstone offering 50 km, 25 km and 10 km loop options with covered rest stops, GPS tracking and weekend camping. Medical support, catering and shuttle transfers are provided.

Experience the iconic trails of Surrey with a choice of three distances through woodland paths and ridgelines. Enjoy a chip timed challenge featuring elevation and scenic views at Box Hill.

A guided 13 mile trail half marathon in the Chiltern Hills with around 300 m ascent, grouped running with qualified leaders, a halfway refreshment point and a finisher's medal.

Fortitude Ultra at Pippingford Park is a 10 hour, 10 lap endurance challenge on roughly 3, 4 and 5 mile loops with up to 215 m elevation per lap. Finishing grade is set by the shortest loop completed and entrants receive a medal and shirt.

Experience an autumn trail run through ancient woodland at the Epping Forest Wildwood Trail Series. Choose between a 10K or Half Marathon course on fully marked paths with a strong focus on sustainability.

Commando Series at Hever Castle on 10 and 11 October 2026 offers 3K, 6K and 12K obstacle mud runs modeled on Royal Marines training, plus a two hour survival experience and an event village with music and attractions.

Choose a scenic 10k or shorter 5k through the Chiltern Hills around Frieth, combining woodland paths and country roads. Expect rolling climbs and panoramic views for a rewarding, hilly challenge for road and trail runners.

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.

The FOOBS Trail and Fun Runs return in October. Choose from a chip timed 10K, 6K, or a family friendly 2K fun run through the countryside near Old Basing. The event supports local schools through community fundraising.

A flat, single lap 10K on 11 October 2026 around the Dengie peninsula with coastal sea wall and countryside sections, finishing at Dengie Hundred Sports Centre. Free parking and changing facilities are available.

Experience a scenic 15 km trail run starting from Tring and traversing the Ashridge Estate. This historic race features the Ridgeway path and provides participants with the choice of a finisher t-shirt or planting a tree.

A 100 mile trail race based at Goring & Streatley on the Thames Path and Ridgeway, run as four 25 mile out and back legs. The event features 16 aid stations, a 28 hour cut off, medical cover and specific qualification and kit requiremen..

An annual cross-country challenge walk, jog or run of 25 km or 50 km across footpaths and tracks in Kent, Surrey and Sussex, with checkpoints, food provided, GPX route files, and first aid cover.

Trail races through Bedgebury National Pinetum offering Half Marathon, 10k and a junior race with route maps, GPX files, a bespoke medal and free photographs.

Beachy Head Marathon Weekend is a multi-distance trail event at Bede's Prep School on 24 October 2026. Races include Ultra, Marathon, Half Marathon and 10k; runners note scenic, hilly routes and strong volunteer support.

A 47 mile point to point ultra along the Thames Path from Iffley to Henley on Thames, with mixed trail and road terrain, five aid stations, mandatory kit requirements and real time GPS tracking. The event has an 11.5 hour cut off.

A 30 mile out and back along the River Stort and Lee Navigation on mostly flat grassy and gravel trails, with checkpoints every five miles, electronic timing and a finisher medal; trophies for the top three men and women.

Wight Lines is a mixed terrain coastal run at Milford on Sea with views of the Isle of Wight. Runners choose distances from 5K to ultra marathon and complete 5.3 km laps, with on course aid and a finishers medal for one lap or more.

Experience a timed anti clockwise loop around Canvey Island featuring sea wall paths and coastal trails. This self supported adventure includes a unique pub check point and follows the scenic King Charles III England Coast Path.