Trail Running calendar near Medstead 2026-2027

Take on the Compton Downland Challenge on 16 May 2026, choosing the marathon or a scenic 16 mile route across the Berkshire Downs and Ridgeway. Expect rolling trails, countryside views, on course aid and a hand thrown mug at the finish.

Join the Semington Slog on 16 May 2026 for a scenic 10K or family 2K around the village, canal towpath and leafy lanes. A friendly community fundraiser at St Georges School with marshalled routes, children’s activities and tasty food, plus..

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

Run from Tudor Sudeley Castle through the rolling Cotswold Hills on scenic trails and historic paths. Distances from 7 km to 50k welcome all abilities and the event is dog friendly.

Take on the Reigate Priory Park 10K on 17 May 2026, a measured four lap cross country route through scenic Priory Park. Open to ages 15 and over, this England Athletics affiliated race supports Sport In Mind and offers medals and trophies.

Run the scenic loop at Hurtwood Park Polo Club in Cranleigh, Surrey with distances from 5 km to ultra on mostly flat off road trails. Multi lap format and a seven hour time limit suit all paces and every finisher gets a memento.

Join the Deddington Four Farms Challenge on Sunday 17 May 2026 for 5k and 10k routes around the picturesque parish of Deddington. Open to experienced runners, fun runners and families, it is a friendly event supporting local charities.

Stort10 '26 at Cammas Hall Farm on 17 May 2026 offers scenic 10 and 5 mile off road loops through farm tracks and woodland with a friendly low key vibe. Finishers get a medal and a premium T shirt or a tree planted in their name.

Join the Portcullis Trail 10 km in Langport on Sunday 17 May 2026 for a scenic run across the Levels, droves and countryside around Cocklemoor. Expect mixed trail terrain and a friendly community vibe; no headphones or dogs.

Run the South Downs 50k, a scenic point to point trail from Falmer to Eastbourne finishing beneath the white cliffs of Beachy Head. Expect about 3500 feet of climb, four aid stations and live GPS tracking.

Run the London to Brighton Ultra Challenge, a scenic trail across the North and South Downs with distances from 100 km to 10 km. Pick a single day or relaxed two day route with rest stops, camping and full support along the way.

The Fox invites trail runners to Surrey on 23 May 2026 with 20K, 41K and 62K routes starting from local villages. Courses are well marked with regular aid stations and a shared finish in Godalming.

Experience a scenic 13.5 mile single loop along the South Downs Way, through Friston Forest and past the iconic Seven Sisters cliffs and Beachy Head. Mostly trail with about 1,900 feet of climbing, full race support and a finisher medal.

Run the scenic Richmond Park Marathon, a 26.2 mile trail race through ancient woodlands and open parkland over three laps. UK Athletics affiliated and charity supported, it offers chip timing, aid stations and medals for all finishers.

Queen of the Suburbs Ultra invites runners to explore Ealing's greenways, towpaths and parks with 50k and 25k single loop options. Expect a Horsenden Hill climb with city views to Wembley and a friendly local race atmosphere.

Run across Dorset from just south of Salisbury to the Jurassic Coast on mostly trail with minimal road running and support along the route. Choose from 100 km, 50 km or a 20 mile Purbeck Traverse for a rewarding coastal challenge.

Join the Rebellion 10km at Riverwoods, Marlow on 25 May 2026 for a scenic trail run along the Thames including a crossing of Marlow Bridge. Finishers get a medal, a Rebellion beer or non alcoholic alternative and a pint cup.

Beat The Sunset 50km in Maidenhead is a single lap, mostly off road ultramarathon along the Thames Path, Jubilee River and Green Way. Flat and scenic, the fully signed course features checkpoints, chip timing and post race mementoes.

Tackle the full Ridgeway in an 86 mile point to point trail from Ivinghoe Beacon to Avebury Stones, with rugged views, checkpoints and solid race support. Limited field makes this a classic long distance test for experienced trail runners.

Run 50 km along the scenic River Medway from Rochester to Tonbridge, mostly flat towpaths and trails with a final lap on the athletics track. Live timing, aid stations and bag transfer make this a tidy and rewarding ultramarathon.