Winchelsea Beach
Trail Running Calendar near Winchelsea Beach 2026-2027
Explore the top trail runs near Winchelsea Beach for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
Experience the historic trails of Kent with 25km, 50km, or 100km races featuring scenic woodlands, castle views, and a festival style race village.
A 12 km team navigation endurance challenge along the Seven Sisters and South Downs Way with load bearing and non load bearing categories.
Six hour trail event at Bates Green Farm where runners complete as many 3.6 mile laps as they choose, solo or in relay, with a vegan friendly cup free aid station.
Obstacle course weekend at Pippingford Park on 26–27 Sep 2026 with Sprint, Super, Beast, Ultra, Kids races and the British OCR Ultra Championship.
A 10 mile TRA licensed trail race at Eridge Park on 27 September 2026, with steep climbs, muddy terrain, route maps, a finisher memento and a pint and cake at the finish.
A 5km handicap trail race in Firle on 27 September 2026 with a mostly hard track route, prizes, a 50 runner limit and tea and cake after.
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.
Commando Series at Hever Castle on 10 October 2026 features 3K, 6K and 12K military style obstacle courses with age specific entries and an event village.
Trail races at Bedgebury National Pinetum and Forest offering a half marathon and 10k with medals for finishers and prizes for top finishers.
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 8 km trail loop around Herstmonceux with over 70% trail, course marshals, prizes 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.