Medstead
Trail Running Calendar near Medstead 2026-2027
Explore the top trail runs near Medstead for 2026-2027! We've gathered 145 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
Off road races at Longmoor across sand dunes, ponds and mud with single and two lap options and medals for all finishers.
January 2027
Kickstart the New Year with a relaxed 5 km loop at Lee on the Solent Beach featuring spot prizes and food bank donations.
A guided 30 mile trail run from St Martha's Hill exploring the Surrey Hills and Box Hill with an experienced ultra runner and coach. Group pace, recommended 22 miles training, cost £55 and an alcohol free beer may be available.
Timed out and back event on The Itchen Way in Winchester with flexible starts, lap distances from 2.62 miles up to ultra distance, and on-course vegan options.
A winter trail run near Winchester with two off-road routes around Farley Mount, chip timing, on-course support and a finisher medal.
A flexible 7 hour time challenge along the River Thames in Staines offering distances from 3 km up to 50 km, medals, distance pins and on-course aid.
February 2027
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.
Single-loop trail races of 50 miles, 50K and 20 miles around Ditcham Park School in Hampshire, following parts of the Staunton and Monarchs Ways and the South Downs Way.
A two-day, 66-mile ultramarathon along the North Downs Way with organised logistics, on-course support, and overnight accommodation.
Two coastal half marathons in Portsmouth and Langstone Harbour over a Valentine weekend with an optional ferry crossing and a bonus medal for completing both.
Saturn Running's Midweek Chasing Numbers in Staines is a seven hour time challenge along the River Thames with flexible lap distances and finisher medals.
A 30 mile non-competitive group trail run from Harting Down along parts of the South Downs Way, passing Beacon Hill, Cocking Down and Kingley Vale. Led by an experienced guide and recommended for those who have run at least 22 miles in training.
Coastal trail running around Chichester Harbour with 21.3k and 16.1k routes, a low-tide foreshore crossing, chip timing, finisher medal and on-course support.