Trail Running calendar near Windsor 2025-2026

The Goring Gap Trails event, held in Mapledurham near Reading, offers a variety of running and walking challenges, including a 50-mile ultra, a 52K ultra, and a half marathon, alongside walking options of half marathon, full marathon, and a..

The Chiltern Hills 100K is a scenic, challenging ultra around the Ridgeway, visiting Ivinghoe Beacon and Ashridge. Limited to 250 runners and UTMB World Series index race, this May event has rugged trails, great support and a Chesham finish..

Join a friendly, inclusive weekend of trail running and festival fun at scenic Deene Park near Corby on May 9 and 10 2026. Pick from short loops, an evening 10k, a hilly half marathon or the full challenge, with medals for all finishers.

Test your limits at Brighton Backyard Ultra in Stanmer Park where runners tackle a 6.7 km loop each hour until a solo lap crowns the winner. A friendly but fierce endurance event in beautiful parkland with basic on site facilities.

Join the Ridgeway 40 on May 9 2026 for a scenic 40 mile walk along the Ridgeway across chalk downland. Limited entries and checkpoint support make this a rewarding challenge for prepared walkers.

Halstead & Essex Marathon offers an annual road race on scenic low traffic roads through rolling hills, woods and farmland. Run by Halstead Road Runners as they mark their 40th year, it blends competitive spirit with a friendly club vibe.

The Zig Zag Marathon and Half Marathon take place at the Suffolk Running Centre in Bury St Edmunds, UK. The marathon follows the officially measured, scenic Kirtling Route, which is fully on road and mildly undulating, while the half marath..

Take on the Greenway Challenge in Letchworth Garden City: a self guided 13 mile clockwise run starting and finishing at Standalone Farm. Enjoy marshalled crossings, a wooden medal, and cake at the finish while supporting Headway Herts.

Shires and Spires is a friendly multi distance loop from Naseby Village Hall offering races from 10 km to a 35 mile ultra across scenic trails and country roads. Routes alternate each year and GPS files plus live tracking guide runners.

Take on the Midhurst Milers Cocking 10k Trail, a scenic but challenging 10k across the South Downs with a steady climb and a fast downhill finish. Licensed and chip timed with medals, prizes and a lively race village.

Join the Oliver Fisher 10k, 5k and junior run at Milton Creek Country Park for a scenic off road race supporting the Oliver Fisher Special Care Baby Trust. Enjoy park views, medals and fundraising for the neonatal unit.

Race through the rolling vineyards at Rathfinny Wine Estate on scenic, undulating off road trails with 10.7 km single loop or 21.4 km two laps. Enjoy aid stations, eco friendly practices and a relaxed Tasting Room finish.

Tackle the scenic and challenging North Downs Way 50, a 50 mile trail run from Farnham to Knockholt Pound on 16 May 2026. Expect rolling hills, great trail views, well stocked aid stations and a friendly Centurion Running race atmosphere.

Join the Semington Slog on 16 May 2026 at St Georges School for 10k and 2k routes through the village and along the Kennet and Avon Canal towpath. Family friendly fun with marshalls, refreshments and a Slog Dog for every finisher.

Run the scenic Berkshire Downs at the Compton Downland Challenge on 16 May 2026, with 26.8 mile or 16 mile trail options along the ancient Ridgeway. Expect climbs, muddy paths, aid stations, chip timing and a hearty post race BBQ.

The Reigate Priory Park 10K is a scenic charity fun run held in Priory Park, Reigate, Surrey. The course features a 250-meter start plus four laps on an accurately measured, gently undulating cross-country terrain surrounded by lush greener..

Take on the London to Brighton Ultra on 23 and 24 May 2026, a scenic 100 km trail from Richmond to Brighton with about 1500 m of climb across the North and South Downs. Shorter distances, one and two day formats and camping are available.

Run 50 km along the South Downs Way from Falmer to Beachy Head across rolling chalk downs, farm tracks and woods. Mostly runnable with 3,600 ft ascent, it finishes dramatically on the white cliffs for stunning coastal views.

The Fox is a scenic trail run in the Surrey countryside on Saturday 23 May 2026, offering 20K, 41K and 62K races for all abilities. All races finish at Burys Field, Godalming, with marked courses and stocked aid stations.

Farmmageddon is an endurance weekend at Hyde Hall Farm offering looped trail racing on a scenic 5.3 km course. Choose from timed challenges up to a 100 mile two day event with buckle and medal rewards for finishers.