Trail Running calendar near Chesham 2026-2027

Enjoy a scenic 8.5 km trail loop around Northiam, passing Great Dixter, rolling fields and woodland and a final uphill to the village hall. With just 60 places, marshals on course and tea and cake after, this intimate winter race is a delig..

Tackle muddy trails and steep climbs at the May Hill Massacre, a scenic cross country run around May Hill in Gloucestershire. Choose a 7 to 8 mile route or the longer 14 to 15 mile Mayhem loop, with a canicross option and limited entries.

G3 no.2 brings a friendly winter race to Hound House Road, Surrey on Saturday 31 January 2026. Pick a 10 km or 15 km route and enjoy clear signage, field parking and a welcoming series atmosphere.

Oxford Town v Gown is an inter-club orienteering event in Oxford organised by OUOC and TVOC, featuring a roughly 6 km course with artificial barriers and team entries as Town, Gown or N A.

Enjoy a scenic 10K through Lavenham's old railway line, forest trails and quiet rural roads on Sunday 1 Feb 2026. All finishers earn a medal and top three men and women take trophies in this cupless, friendly trail race.

Run a 48 mile point to point ultramarathon along the scenic Peddars Way from Knettishall Heath to Holme next the Sea on 1 February 2026. Enjoy remote rural paths, on course support and a bespoke wooden finishers medal.

Run through Bedgebury National Pinetum on undulating pine forest trails with 10 mile, 5 mile and junior options on 1 February 2026. Enjoy bespoke medals, free photos, trophies and easy parking by GoApe for a winter trail challenge.

Take on the Charnwood Hills Race on 1 February 2026, a scenic but testing 14.5 mile fell route through Bradgate, Broombriggs and Beacon Hill with rough underfoot and about 1,200 feet of climb. Entries are limited and pre entry is required.

Join the Dry January 10k at Willen Lake, Milton Keynes on 1 February 2026 to run 5k or 10k in person or virtually while supporting Alcohol Change UK. Enjoy a bespoke medal, charity technical t shirt and a fun lakeside route.

Guided 10 km trail run around the Devil's Punchbowl in Hindhead, with summer sunset runs and headtorch group night runs in darker months. Social pace, great views and the chance to try trail gear.

Dark Rose is a 5.5 mile trail race around Great Waltham with a small 75 runner field and self navigation route given on the day. Finish back at the Rose and Crown for a hearty cottage pie or vegetable lasagne.

Nighttime street orienteering in Basildon as part of the Essex Winter Midweek Series 2025/26. MapRun is used and two score-format courses are offered with series points awarded using an age and gender handicap system.

The Pilgrim Challenge will take place in Farnham from Saturday 7 February 2026 to Sunday 8 February 2026. You can run 66 miles.

The Westonbirt Arboretum Winter Night Race is a unique running event set in the stunning National Arboretum, featuring over 2,500 tree species. Participants can choose between 5km and 10km routes, which offer a beautiful and varied landscap..

Hibernal Hills opens the season with a single loop in Hampshire on runnable but undulating trails with some long climbs. Choose 50 mile, 50 km or 20 mile routes, waymarked with live tracking and chip timing.

Trail running at Amberley Museum in West Sussex with three waymarked routes on the South Downs Way. Distances range from 6 km to 22 km, with on course outposts, a reusable cup policy and free parking.

Run two scenic coastal half marathons in Portsmouth and Langstone Harbour over one weekend, enjoying harbour trails, seafront promenades and an optional ferry crossing. Complete both to claim the limited edition "Double Trouble" medal.

Drama Llama Run on the Thames towpath offers timed laps on a flat 5.3 km out and back course with a seven hour limit and a flexible start window. Pick 5 km to ultra and enjoy race support, same day results and a finisher medal.

Run the Wivenhoe 5 mile trail on 07 Feb 2026, starting and finishing at The Black Buoy pub near the station. Limited to 50 places, with a celebratory drink for finishers.

Discover The Brails on Saturday 7 February with four colour orienteering courses catering from beginners to experienced navigators across scenic estate land near Hungerford and Marlborough. Entries are online only so book early and come pre..