Trail Running calendar near Cupar 2026-2027

A running festival at Glamis Castle offering 1 mile, 5k and 10k routes to run or walk in support of Maggie's Dundee. Registration is £30 and entrants receive a t shirt and finishers medal.

A 50 km fell running event around the Cheviot Hills near Wooler on 19 September 2026. GPS navigation is required and there is an 11 hour time limit; aid stations, marshals and medical cover are provided.

A varied-terrain 10k around Loch Long near Arrochar on 19 September 2026, organised under UK Athletics rules with chip timing, medals for finishers and category prizes, and post-race prize giving and homemade cakes.

A single loop trail marathon in the Cairngorms National Park on 20 September 2026. The 26.2 mile course is about 80% trail and 20% road, starting and finishing in Kingussie with a finisher medal, T shirt, on site food and prizes.

A trail ultra across the Ochil Hills offering 30 mile, 50 mile and a limited 100 mile option. Marked routes include checkpoints with water, GPS tracking and chip timing, with medals for all finishers.

The Pilgrims' Ultra is a trail running series on the historic St Oswald's Way in Northumberland. Runners can choose from 50 km, 100 km, and 100 mile distances, starting on Holy Island. The event includes GPS tracking, a T-shirt, and a medal..

A 30 km hill race from Traquair House to Broughton Ales across the Scottish Borders with roughly 1500 m of ascent. The route uses hill tracks and open heather, has eight marshalled checkpoints and requires mandatory emergency kit.

Trail running festival at Dalkeith Country Park near Edinburgh offering distances from a family mile to an ultra marathon. Courses use woodland trails, firm paths and grassy sections, and one well controlled dog per runner is allowed.

Three trail races take place on the grounds of Floors Castle in 2026, with options of 10 km, 5 km and a Junior 3 km. Courses use hard packed gravel trails and finish on the castle lawn with estate access and event facilities.

A multi-discipline mountain race from Kinlochleven featuring a Loch Leven swim, mountain and gravel bike sections and a run up Ben Nevis. The 73 km route includes 7,874 ft of elevation.

Mud Madness at Chatelherault Country Park mixes obstacles, water hazards and muddy fun with a 1 km children’s run and a 5 km family run; entries and family tickets are available through the organiser.

A 57-mile point-to-point ultramarathon from Glasgow to Edinburgh following canals and towpaths, with live GPS tracking, staffed checkpoints and a 16 hour cut-off. The event is limited to 750 places and requires prior marathon experience.

Run through Scottish history at the William Wallace Running Festival. Choose between a fast, flat 10km past Stirling Bridge or a family-friendly 1 mile fun run. Both events start and finish at Stirling Cricket Club on 10 October 2026.

Take on the Bennachie Ultra Marathon, a scenic yet demanding 50k across Bennachie peaks with over 5000 ft of climb on trails and moorland. Limited pre entry places make this October classic a must for experienced trail runners.

A trail running festival in Aberfoyle on 10 October 2026 that marks its third edition, featuring the returning half marathon and a 63 km ultra across multiple race options.

A Speyside running event offering marathon, half-marathon, 10 km and a four person relay along the Speyside Way, with distilleries on the route and whisky miniatures available at the finish.

An eight hour loop challenge at Tentsmuir Forest of 4.366 mile laps tracked by wrist timing tags; laps count toward half, full or ultra distances and Basecamp offers kit storage and race support.

A hill race from Alva Glen through the Ochils covering 14.6 km with 966 m of climb, visiting summit checkpoints including Ben Cleuch and The Nebit. Registration is at Alva Scout Hall and basic facilities and prize categories are provided.

Experience a 38 mile ultramarathon or team relay through the scenic landscape of Jedburgh. Enjoy a fully marked course with electronic timing, professional support stations, and a welcoming post race meal for all finishers.

Join the Halloween themed Auchterarder 10K Chilli Trail on 31 October for a fun, chilli pepper shaped route into the Ochil Hills with forest trails, stream crossings and sweeping views. All finishers get a snood and a bespoke medal.