Rye
Trail Running Calendar near Rye 2026-2027
Explore the top trail runs near Rye for 2026-2027! We've gathered 39 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A multi-distance trek and trail event along the South Downs Way from Eastbourne to Arundel with scenic sections including Beachy Head and the Seven Sisters. Distances of 100 km, 50 km and 25 km are supported with rest stops, medical teams, camping an..
A bi-annual trail race around Bewl Water in Kent offering 10 km, half marathon, marathon and 50 km ultra on wooded trails and quiet lanes.
A multi-terrain trail race from Rye Sports Centre in East Sussex offering 30k (slightly over 30 km) and 15k routes through the High Weald AONB. The course links historic churches and passes woodlands, orchards, country lanes and coastal views.
A trail running weekend at Loddington Farm on 19 September 2026 with 25 km, 50 km and a single loop 100 km linking Kent's North Downs, Greensand and Weald Ways.
A 12 km team navigation endurance challenge along the Seven Sisters and South Downs Way with load bearing and non load bearing categories.
Obstacle course races at Pippingford Park on Sep 26 to 27, 2026, with Sprint, Super, Beast, Ultra and kids races across rolling, sometimes wet countryside.
A 10 mile traffic free trail race at Eridge Park on 27 September 2026 featuring steep climbs, muddy sections and finish-line cake with a free pint.
A picturesque 5 km handicap trail run from Firle Village Hall on undulating tracks, with prizes, marshals, post-race tea and a limit of 50 entries.
October 2026
Looped trail event near Maidstone offering 50 km, 25 km and 10 km options. The route follows the North Downs Way and River Medway and includes covered rest stops, GPS tracking and camping at basecamp.
A military inspired obstacle mud run at Hever Castle on 10 October 2026 offering 3K, 6K and 12K courses, junior options, and an event village with spectator attractions.
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.
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.
An 8km trail loop around Herstmonceux with over 70% trail, entry limited to 60 runners, prizes for first male and female, and tea and cake after the race at the village hall.
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.
Off road marathon and half marathon south of Canterbury with live tracking, checkpoints, mandatory kit lists, event HQ facilities, and a charity donation from entries.
November 2026
A 6.66 mile woodland trail run at Kings Wood near Ashford featuring muddy, hilly and technical sections, limited to 200 runners and organised by Ashford Tri Club.
December 2026
A self-navigated festive night trail of about 5 miles through Friston Forest and downland, with medals, a bar perk and a fancy dress dessert prize.
A 50 km trail ultra along the North Downs Way from Detling to Wye with about 1,000 m of ascent, three checkpoints and mandatory kit requirements. The route passes Boxley Warren, Thurnham Castle, Lenham Cross and the Wye Downs.
January 2027
An annual New Year five mile cross country in Penshurst village over rolling hills and woodland trails. Open to ages 10 and above with entry fees supporting Hospice in the Weald and awards across junior, local and canicross categories.