Trail Running calendar near Rye 2026-2027

The East Grinstead 10K will take place in East Grinstead on Sunday 4 October 2026. You can run 10 kilometers.

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.

Tackle the Kent Downs on Saturday, 10 October 2026. Choose from 50 km, 25 km, or 10 km looped routes starting from the Maidstone basecamp. Enjoy full support with rest stops, food, and a celebratory finish line.

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.

Test your endurance at Pippingford Park with 10 laps in 10 hours. Choose between three different loop distances on a private estate and earn your finisher shirt based on your performance in this unique timed challenge.

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.

Experience a 20 mile looped trail run starting and finishing inside the historic 18th Century Landguard Fort. Runners will cross nature reserves and river estuaries along the diverse Suffolk coastline.

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.

Run a scenic and flat 10k course featuring coastal paths along the Dengie peninsula and town streets. Starting at the Dengie Hundred Sports Centre, this event offers free parking and a variety of terrains for all participants.

The Frappadingue Gravelines will take place in Gravelines on Sunday 11 October 2026. You can run between 6 and 12 kilometers.

Join this annual cross country challenge through the footpaths of Kent, Surrey, and Sussex. Choose between 25km and 50km distances with full checkpoint support and post event catering included.

Run through the narrow, traffic-free trails of Bedgebury National Pinetum & Forest. Choose from a half marathon, 10k, or junior race on a scenic woodland course. Every finisher gets a bespoke medal and free photos.

Experience a premier trail running weekend in Eastbourne featuring an ultra, marathon, half marathon, and 10k. Run along the scenic Seven Sisters with well stocked aid stations and a supportive atmosphere for all participants.

Experience a scenic 30 mile ultra marathon along the River Stort and Lee navigations. This flat out and back course offers a fast trail experience with generous cut off times and supportive checkpoints.

Experience an off road running event south of Canterbury featuring scenic trails through the Kentish countryside. Choose between a way marked half marathon or a self navigated full marathon with full event village facilities.

Explore the Essex countryside on a 26 or 18 mile figure of eight course via Blackmore. This self sufficient event offers multiple checkpoints and a finishers meal as part of the Essex and Herts Triple Challenge.

A 5 mile timed, self-navigated night trail on 30 October 2026, run mostly through forest and downland. Fancy dress is encouraged with trophies and a post-run dessert for winners, and a tail runner will sweep the course.

An autumn/winter ultra on classic Chiltern trails. This single-loop 50K starts in Berkhamsted, following The Ridgeway and Chiltern Way with scenic views. The fully-marked course has a 9-hour limit and is a UTMB World Series Index Race.

Experience a festive 6.66 km Halloween trail run starting and finishing at a local brewery in Chelmsford. Participants enjoy a costume focused event with medals and drinks for finishers in a social atmosphere.

Experience a night trail run through the ancient Alice Holt Forest with 5 km, 10 km, or 15 km lap-based routes. Navigate tree-lined avenues by head torch and enjoy fire pits and refreshments at the finish line.