Trail Running calendar near Greater London 2025-2026

Run along the banks of the River Thames in Henley with half marathon, 10K and junior races, chip timing, unique medals and free race photos. Event village serves food and drinks and the event supports the Royal Berks Charity.

Run the Rosebud Marathon, a scenic 26.2 mile leg of the Rose of the Shires Ultra across Northamptonshire with roughly 60% trail and 40% road. Enjoy varied terrain, aid stations and live GPS tracking to Brixworth Country Park.

Run the spring trails at Cowdray Estate with 5 km, 10 km, 10 mile, junior races and canicross options. Scenic sandy heathland and mixed trail sections through wildlife rich commons deliver a rewarding, characterful day out.

Tackle the rolling hills and chalky trails of the South Downs at the Maverick East Sussex Trail Run in Stanmer Park, with routes from 5 km to 21 km and a climb past Ditchling Beacon. Scenic, timed and medal for finishers.

Haughley Festival of Running brings multi distance races at Haughley Park, from 5k to ultra, on lap based scenic routes with on site parking. Limited to 300 entrants for a friendly, village festival feel.

Scenic loops from Windsor Racecourse through Windsor Great Park and along the Thames past Windsor Castle, offered as 50 km, 25 km and 10 km races. Well supported with aid stations and a festival finish with medal and T shirt.

The Chiltern Ridge Classic 50k will take place in Wendover on Saturday 18 April 2026. You can run 51 kilometers.

Run the Spring Trail Series at Cowdray Estate in Surrey, following the scenic Serpent Trail through greensand hills and woodland. Choose from 12km to 110km, with relaxed cut offs, campsite and on site expo for a friendly well supported day.

Take in Seaford seafront and rolling South Downs on the Martello Half Marathon, an undulating trail course that blends coastal views with countryside. Enjoy water stations, a bespoke medal and free event photos as you race.

Join the Grand National 10km Trail Run in Findon on 19 April 2026 for scenic South Downs trails and a fun family atmosphere. Choose from canicross, 10k, 5 mile or a kids run while supporting St John the Baptist Primary School.

Run the scenic Thames Ring, a multi distance trail loop from Streatley on Thames that follows the river and canals. Choose 100, 150 or 250 mile challenges on riverside paths with GPS tracking and checkpoint support, 22 to 26 April 2026.

Take on the Ale Trail 15 mile through scenic Alfriston, East Sussex, starting and finishing at Ye Olde Smugglers Inne beer garden. Tackle country trails and enjoy staffed pub checkpoints with beer tokens and local camaraderie.

Take part in The Other Run in Bury St Edmunds on 26 April 2026 with 5k, 10k, half and marathon options on scenic country roads. Enjoy a bespoke finisher medal, friendly atmosphere and a seven hour marathon cutoff.

Blindfolded and dropped at an unknown location, The Drop in Winchester challenges solo runners and teams to find their way back over 10 or 15 miles as the crow flies. No maps or GPS allowed, just navigation, grit and a taste for adventure.

Run through fragrant bluebell woods on the scenic Angmering Park Estate with 10 mile and 10 km options for trail lovers. Enjoy marshalled courses, bespoke medals and free race photos at this popular spring event.

Run scenic undulating trails in Alice Holt Forest with options from a junior dash to a half marathon across looped routes. Enjoy a friendly atmosphere while supporting GUTS, raising funds for bowel cancer early detection.

Join NOT the London Marathon Run 2026 on Sunday 26 April in Walton on Thames for a flat, certified lap course along the riverside towpath. Choose marathon, half or a 7 hour timed challenge, enjoy flexible starts and a commemorative medal.

Saturn’s Midweek Chasing Numbers 7-Hour Time Challenge is held at Wraysbury Skiff & Punting Club on the River Thames. The event is designed to be affordable and flexible, inviting all abilities to run or walk within a 7-hour window. Partici..

Explore the Isle of Wight Challenge along the coastal path from Chale past the Needles, Cowes and Ventnor, with options from 10 miles to 106 km. Fully supported with rest stops, GPS tracking, catering and a finishers medal and T shirt.

Take on the Thames Path 100, a 100 mile point to point run from Richmond to Oxford along the scenic Thames with marked trail, plentiful aid stations and a 30 hour time limit. A classic endurance test for experienced runners.