Trail Running calendar near Cupar 2026-2027

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.

An 11 km hill race near Monymusk on 26 September 2026 with 430 m of climb and pre-entry only registration; listed 2024 fees are shown and parking is at Monymusk Village Hall.

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.

On 27 September 2026 the Floors Castle Trail Race offers 10km, 5km and a Junior 3km through the castle grounds and woodlands, with a race village on the main lawn and a finish line in front of Floors Castle.

A multisport mountain event in Kinlochleven featuring a loch swim, mountain and gravel bike sections along the West Highland Way, and a run to the summit of Ben Nevis. Total distance about 73 km with significant elevation gain.

Mud Madness at Chatelherault Country Park on 4 October 2026 offers a 1 km kids course and a 5 km family mud run with obstacles, water hazards and staggered waves, plus on-site parking, registration t-shirts and finishers' medals.

A 57 miles ultramarathon from Glasgow to Edinburgh along canals and towpaths, with GPS tracking, mandatory kit requirements and a 16 hour cut off. The event has 750 places and is scheduled for October 2026 and October 2027.

A 70 km circular mixed terrain ultra in and around historic Stirling, offered as solo entries or team relays of three or six, with aid stations, GPS live tracking and an overall 14 hour cut off.

A 50k mostly off-road ultramarathon on Bennachie with over 5000 ft of ascent, visiting multiple peaks and starting and finishing at the Bennachie Visitor Centre. Pre-entry only with 150 places and a 4 hour cut-off at about 19 miles.

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.

The Up and Running Events - Chatelherault Country Park will take place in Ferniegair on Saturday 17 October 2026. You can run between 6 and 20 kilometers.

An eight-hour looped trail event at Tentsmuir Forest where runners complete 4.366 mile laps to accumulate distance. Laps are timed by wrist tags; 3 laps equal a half marathon, 6 a full marathon and 7 or more an ultramarathon.

A 14.6 km hill race with 966 m of ascent through Ochils Woodland Park, visiting Andrew Gannel Hill, Ben Cleuch, Ben Ever and The Nebit, with registration at Alva Scout Hall and prizes for top finishers and age categories.

A 38 mile trail ultramarathon with a relay option held in association with the Jedburgh Running Festival. The event on 24 October 2026 is presented as LGBTIQ+ and nonbinary friendly, with entries opening 1 March 2026 at 8pm.

A two day self reliant mountain marathon in Scotland on 24 and 25 October 2026. Teams navigate with map and compass, carry overnight kit and choose between line or score courses across a rugged event area.

A *10 km* trail race from Auchterarder into the Ochil Hills with forest trails, stream crossings and a route shaped like a chilli pepper. Online entry, 16+ age limit, goody bag with snood and medal, prizes for finishers and costumes.

Trail Outlaws stages Dark Skies Run @ Wooler in Northumberland with fully marked trails, stocked check points and options for a Trail 10k or a Half Marathon. Entry fees shown range from £25 to £36.

A scenic trail half marathon around Dalmeny Estate and Cammo Nature Reserve near South Queensferry. The chip timed 13.1 mile course has under 1000 ft of ascent and includes a finisher medal, prizes and on site facilities.