Trail Running calendar near Kirkcaldy 2026-2027

We have found 118 Trailruns within 80 miles of Kirkcaldy. See below where and when you can find the races.

Run the Borders is a 109 km loop on the Borders Abbey Way passing four ruined abbeys and historic towns. Options include a 50K, the full 109 km and a four person relay on mixed tarmac, trails and riverbanks.

Chase summer evenings in Edinburgh with the Sundowner 5K Series, a relaxed yet competitive run across three scenic city parks. Enjoy chip timed racing, lively warm ups and post race photos as you test your speed over 5K or the full series.

Join the Eyemouth Twilight 5k on 28 August 2026 for a chip timed coastal evening run with medals for finishers. Family friendly Scott's Mini Fun Runs, goodie bags and Giacopazzi's Gelato at the finish make it a fun seaside outing.

A 53 mile point to point trail ultramarathon on the southern West Highland Way from Milngavie to Tyndrum, with live chip timing, extensive finish facilities and specific entry and kit requirements for runners aged 20 and over.

Join this lively fell race at Bellingham Showfield as part of the country show, tackling 4 miles with 600 ft of climb across classic Northumberland terrain. No pre entry required; runners aged 16 and over can sign up on the day.

September 2026

A trail running event at Kielder Castle on 5 September 2026 offering five route distances from 5 km to 52 km across forest trails with varied elevation. Camping, marked and timed courses, outposts and a plastic free policy are included.

A 40 mile annual ultra-marathon along the River Ayr Way, held in September as part of the Scottish Ultra Marathon series. The route follows a 44 mile source to sea path with waymarking, route maps, and a temporary diversion at Wellflat Bank..

A 30K run in North Berwick with solo and three person relay options, 640 m ascent, chip timing and marshals. A separate 10K circular walk supports Scottish Veterans Residences.

A 50 km trail race in the Cheviot Hills near Wooler on 19 September 2026 that requires GPS navigation. Organisers provide digital and waterproof maps, GPS trackers, aid stations and medical cover; finishers receive a medal and certificate.

Pilgrims’ Ultra offers 50k, 100k and 100 mile ultramarathon options along St Oswalds Way from Holy Island through varied Northumberland scenery. All distances are tracked and finishers receive a medal and T shirt.

Trail races at Dalkeith Country Park in September 2026 cover distances from a family 1 mile to a 32.5 mile ultra. Courses use woodland and estate paths, live chip timing is provided, canicross is allowed and on site parking is available.

October 2026

Run 57 miles point to point from Glasgow Riverside Museum to Edinburgh Athletics Track, passing the Falkirk Wheel and the Antonine Wall. Live GPS tracking and just 750 spots make this an iconic long distance challenge.

UTMB Index

Explore historic Stirling at the William Wallace Running Festival on 10 October 2026, with mixed terrain routes past Stirling Castle and the Wallace Monument. Distances suit all runners from a fun mile to 50 km and 70 km ultras with relay t..

A 10K trail race in Auchterarder on 31 October 2026, with a route into the Ochil Hills featuring mixed surfaces, climbs, descents and stream crossings. Entries were online only with a 650 person limit and are now closed.

Run under the stars at Dark Skies Run in Wooler on 31 October 2026, a Trail Outlaws night trail in Northumberland National Park with fully marked routes and stocked checkpoints. 10k and Half Marathon options.

Start and finish in Alva Glen and tackle a rugged 14.6 km course with 966 m of ascent through Ochils Woodland Park, summiting Ben Cleuch and The Nebit for sweeping views. Prizes for top finishers and veteran categories add competitive appea..

November 2026

Trail running festival at Tentsmuir Forest on 01 Nov 2026 offering a Half Marathon, 10 km, 5 km and a 1.2 km family run. Routes are clearly marked and marshalled and finishers in the main distances receive medals and mementos.

A nocturnal ultra where runners cover a well marked 5 km trail loop as many times as possible in six hours. Solo runners and teams of up to three pass a tented base each lap and race with music, lights and on course support.

A multi-terrain ultra around the Tweed Valley based at Glentress Peel Visitor Centre in mid-November. Two route options, 65 km and 50 km, follow forest trails, riverside paths and open moorland with marked routes and aid stations.

Join the Hermitage trail runs for scenic 10km and 5km routes over Blackford Hill plus a festive 1.2km fun run. Kids get elf hats and all enjoy snacks while proceeds support Friends of the Hermitage and Morningside Primary School.