Trail Running calendar near Cheltenham 2025-2026

Run scenic tracks through ancient New Forest woodland near Brockenhurst, with routes up to 21.6 km and regular sightings of ponies and deer. Chip timing, aid stations and a finisher medal make this a friendly autumn trail event.

Tackle Wendover Woods 50, a demanding 50 mile trail through five scenic loops in Forestry England woodlands. Expect big climbs, technical singletrack and great support, all with a capped field for an intimate race day.

Run the North Chilterns 50K, a scenic trail ultramarathon from Putteridge Bury over Warden, Barton and Pegsdon Hills with sweeping views. Limited to 250 runners, this supported 50 km course is a rewarding late autumn challenge.

Run the scenic flat Thames riverside route in Windsor on 21 Nov 2026 at the Thames Path Trail Run. Pick about 16 or 22 km, enjoy chip timing and a finisher medal, and support the plastic free event by bringing a reusable cup.

Join a guided 10 km trail run around the Devil's Punchbowl in Hindhead, tackling varied hills and stopping at a high point for stunning views. These social group runs are steady paced and run at sunset or at night with headtorches for a fun..

Join the Phoenix Christmas Advent Run in Walton on Thames for distances from 5 km to ultra along a flat riverside towpath. Flexible start times, a 7 hour limit, and finishers receive a medal plus a chocolate advent calendar.

Take on scenic undulating trails around Carsington Water this December with a half marathon or 10k, both looped routes with kilometre markers and on course support. Finishers receive a themed medal, water and post race goodies.

Take on the Cardington Cracker, a 9 mile fell race near Church Stretton with 793 m of climb and breathtaking Border views. Pre entry only and limited parking mean early sign up is essential for this rugged, rewarding test.

Join the Nightmare Before Xmas Trail half marathon on 19 December for a festive, scenic and challenging trail through woodland, steep climbs and muddy sections. With small fields, fancy dress prizes and mince pies, it is a festive challenge..

The Birmingham Black Country Half Marathon is a running event held in the Black Country region near Birmingham. Organized by StuWeb Events Ltd., the race covers the half marathon distance of 13.1 miles. While specific details about the cour..