Trail Running calendar near Pickering 2025-2026

Celebrate the season at Chopwell Woods on 21 December 2025 with festive trail routes for family 1 mile, 4 mile and 8 mile runners through atmospheric woodland. Finishers get medals and mince pies and canicross is welcome.

Join Wharfedale Harriers on 21 December for The Stoop, an 8 km fell race at Penistone Hill Country Park with about 250 m ascent. Expect a festive vibe with a free Santa hat, post race tea and a Curly Wurly, and team entries welcome.

Orienteering at Oakwell Hall country park on Sunday 21 December offers mixed woods, parkland and varied terrain for runners of all abilities. Novice and family courses include navigation help and hireable timing dibbers, so newcomers are we..

Celebrate the shortest day with the Winter Solstice Strider, a magical night run through St Ives Estate in Bingley raising funds for Sue Ryder Manorlands Hospice. Choose a 5k or 10k on multi terrain trails or run virtually and get a bespoke..

Celebrate Boxing Day with the Chevin Chase, a hilly 7 mile road and trail loop around scenic Otley Chevin near Guiseley. Chip timed and supporting local causes, finishers choose a technical shirt or a tree planted in their name.

Celebrate Boxing Day with the Whinberry Naze fell race in Rawtenstall, a punchy 4 mile course with 229 m climb across Pennine fells. Enter on the day for a festive atmosphere, fancy dress prizes and a friendly post race vibe.

Join EPOC MapRun in Greenhead Park, Huddersfield, with routes from 1.4 to 4.9 km for all abilities. Use the MapRun app or grab a map, enjoy the park cafe and return to the Community Room when you finish.

Join the Guisborough Woods Fell Race, a tough 5.5 mile three lap forest course with steep climbs and technical slippery descents. Part of the Dave Parry Lets Run Winter Series, it welcomes seniors, teams and juniors.

Join the Booze Run on Sunday 28 December 2025 in Arkengarthdale for a scenic 9 km trail through the Yorkshire Dales with rewarding climbs and a pub checkpoint in Booze. Friendly atmosphere, on the day entries welcome and prizes for first ma..

Explore York on foot at New Earswick Urban on Sunday 28 December starting at New Earswick Bowling Club. Choose from five courses ranging from family friendly to challenging urban routes, including a junior and family course. Entries close 2..

Bilberry Fields Winter is a friendly Category AS fell race on 29 December 2025 near Todmorden, featuring a well marked 7.4 km course with 371 m of climb that suits beginners. Race HQ is the Hare and Hounds pub where refreshments and prize g..

Ring in the New Year with the Daleside Auld Lang Syne fell race at Penistone Hill on 31 December. A muddy 6.7 mile loop with about 1000 ft of ascent, capped entries and a bottle of Daleside beer included.

Shake off the New Year with the 19th Hangover Hike from The Leggers Inn in Dewsbury, a walking and running event with 10, 17 or 21 mile circular routes that converge at a main checkpoint. Enjoy tea and toast at registration, snacks on route..

Kick off the year with the Clowbridge 5k on New Year's Day, a friendly two lap trail around scenic Clowbridge Reservoir. Organised by Run JMC, this mostly flat, marshalled race supports local causes and offers prizes.

Start the year with the Nine Standards fell race in Kirkby Stephen on 1 January 2026, a challenging 8 mile course with 549 m of climb across classic Cumbrian hills. Pre entry is required and full FRA kit is mandatory.

Celebrate New Year with the classic Captain Cooks Fell Race in Great Ayton on 1 January 2026. A challenging lap to Captain Cook's Monument across steep muddy trails and forest, organised by volunteers with proceeds to charity.

Start the New Year at the Giant's Tooth fell race in the South West Pennines, a punchy 3 mile course with 120 m of climb and sweeping moorland views. Limited to 100 pre entry places, based at the Causeway Foot Inn with Ogden Water registrat..

Start the year on the North Yorkshire coast with Hardmoors 15, a scenic 17.5 mile circular trail from Robin Hood's Bay along the Cleveland Way. Expect sea views, testing climbs, on course support and a finisher medal with a technical T shir..

Hardmoors 30 is a challenging winter trail run from Robin Hood's Bay along the Cleveland Way and Cinder Track, finishing at Fylingdales Village Hall. Expect rugged coastal cliffs, 30 miles with 1040 m ascent, aid stations and strict kit rul..

Run under the Wolf Moon in this scenic out and back trail half in Sutton Scarsdale with undulating woodland and Five Pits Trail views. Finish with a Wolf Moon medal, cake and hot drinks by a campfire and an optional earlier start.