Trail Running calendar near Windsor 2026-2027

Two fully signed Capital Ring routes in London offering a 55 km ultra and a 25 km trail, finishing in Richmond upon Thames. GPX files, feed stations, chip timing and medical support are provided, with enforced cut off times and age limits.

A point-to-point trail event on the Three Shires Way offering a 50 mile ultra and a marathon through Bucks Beds and Northants, with GPX routes, checkpoint support, mandatory kit requirements, prizes and charity donations.

Take on the Phoenix Centaur 100 Mile Ultra at Denbies Wine Estate, a flatish 1 mile off road loop with multiple distance options across the weekend. Enjoy central aid, chip timing and a Centaur medal and buckle for 100 mile finishers.

Run a marathon or half marathon at Denbies Wine Estate on 20 June 2026, tackling a scenic off road loop through the vineyards. Choose attended or virtual entry, enjoy chip timing and a collectible community medal while places remain limited..

A multi-distance trail ultramarathon from West Dean Gardens on 20 June 2026, using the South Downs Way and coastal routes. Distances run from 30 km to 100 km with on-course support, medical cover, food stops and transport options.

Join the Phoenix Hydra 75 Mile Ultra at Denbies Wine Estate in Dorking for a scenic 1 mile off road loop with chip timing and a staffed aid station. Distances run from 12 hour to 100 miles and all entrants receive a free memento.

Run the Maldon Ultras on 20 and 21 June 2026 in Maldon, with 100 mile, 50 mile and 30 mile lapped races across fields, woodland and vineyards with estuary views. Small fields and scenic off road laps make for a friendly yet fierce ultra.

A 21.2 km trail race across the National Trust's Dunstable Downs with about 450 m of ascent, waymarked routes and on course aid. Entry is limited to 300 runners with a 4 hour time limit.

Tackle scenic off road trails at The Martian Race on Horsell Common, with 2 km, 5 km, 10 km and 21 km options for all abilities. Volunteer run and charity focused, this popular event blends nature, challenge and community spirit.

A multi-terrain 10 km event at Twisted Tree Brewery on the private Tusmore Estate in Bicester, with standard and canicross 10 km options. Entry is £32 plus fees and entries close 17 June 2026; finishers receive a medal and a drink.

Community 10 km, 5 km and a free junior run on mixed undulating terrain in Hawkhurst, Kent. The event raises funds for local projects and features finish line cake, a bespoke medal and a complimentary half pint for finishers.

Circular cross country event near Baldock on 21 June 2026 offering routes of 26 miles and 18 miles across undulating Hertfordshire countryside. Entries open 1 March with a limit of 175 places.

A chip-timed trail running event in Trent Country Park, Enfield, offering a 10 km senior race plus junior and kids races, with race photographs provided and specific safety and age rules for participants.

Run the Seasons at Cowdray on 26 June offers scenic 5km and 10km routes plus kids and caniRun options across polo lawns, Cowdray Ruins and the South Downs. Finishers get unique stacking medals, free photos and a BBQ, bar and prize hampers.

Three races at Colworth Estate in North Bedfordshire combine to marathon distance: a 5-mile family run, an 8.1-mile trail and a 13.1-mile half. The event lists free camping and on-site family entertainment.

Trail event at Hyde Hall Farm offering distances from 5k to ultra marathon with lap options for heavy half and ultra. Aid station, baggage area and secure parking are provided and finishers receive a bespoke or lucky dip medal.

A trail running event on 27 June 2026 at Cranleigh Showground with five routes from 5 km to 52 km across the Surrey Hills and North Downs Way. Outposts provide food and self serve water; some long routes require specific mandatory kit.

Gravel Rush Run in Winchester on 27 June 2026 features a 21 km half marathon and a 10 km race at Matterley Estate. Entry fees are listed per participant and a 3% administration charge is added to all entries.

Run scenic off road trails through the Thames Valley at the RunThrough Marlow Trail Run, with 5K, 10K and half marathon options. Enjoy chip timing, a themed medal, free race photos and a lively event village with food and drinks.

A one day multi distance trail running event at Salcey Forest offering 10K, half marathon, marathon and 50 km, on mainly hard packed forest trails. The event is cupless and all finishers receive a medal and a drink.