Cupar
Trail Running Calendar near Cupar 2026-2027
Explore the top trail runs near Cupar for 2026-2027! We've gathered 39 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A long hill race on 15 August 2026 covering 26.07km with 1438m ascent across East and West Lomond. The unwaymarked route follows checkpoints, requires navigation and mandatory kit, and offers prize categories and a GPX file.
A 10km trail run around Bertha Loch and Almondbank on 22 August 2026, using a reverse summer route with technical, muddy sections through woods and gentle hills.
A 12 hour event on 22 August 2026 with repeated 10 km laps around Bertha Loch; solo or team entries, chip timing, water station and live results.
A 5.7 mile off road trail race in Cardenden Woods on 23 August 2026 that passes the historic duel site and features varied, often muddy terrain.
A summer evening 5K series in Edinburgh across Leith Links, Fettes and Inverleith Park with chip timing, finishers' medals and entry options of £12 per race or £30 for all three.
Weekend running festival in Kirkcaldy offering a half marathon, 5 km and 10 km trail races, plus a child friendly Superhero Fun Run and family activities.
A 5K loop at Dunnikier Park in Kirkcaldy on 29 Aug 2026 as part of the Kirkcaldy Parks Running Festival, with mixed surfaces and a one hour time limit.
A licensed beach race in Portobello on 30 August 2026, roughly 4 miles on sand at low tide with proceeds supporting local school and community causes.
September 2026
Mud, water and obstacles in Fife/Kinross on 5 September 2026 with 10 km, 5 km and a 3 km kids course plus free parking and photos.
An hour-long hill loop on Corstorphine Hill where runners complete as many 1 km laps as possible; Scottish Athletics licensed, open to over 18s with 200 places.
A summer evening 5K series in Edinburgh across Leith Links, Fettes and Inverleith Park with chip timing, finishers' medals and entry options of £12 per race or £30 for all three.
A 30K run in North Berwick with solo and three-person relay options plus a scenic 10K walk, chip timing and fundraising for Scottish Veterans Residences.
Running festival at Glamis Castle on 13 September 2026 organised by Maggie's, in person, with tickets priced at £30 and a no refunds policy.
A 5 kilometre trail race through the woodland of Letham Glen on 13 September 2026 with medals for all finishers, prizes for top and local finishers, and a £10 entry fee.
Trail running festival at Dalkeith Country Park on 27 September 2026 with distances from a family mile to an ultra, Canicross option and live chip timing.
October 2026
Eight hour trail challenge at Tentsmuir Forest on 24 Oct 2026 where runners complete as many 4.366 mile laps as possible with wristband lap tracking.
A Halloween themed 10 km trail race in Auchterarder on 31 October 2026 with a chilli pepper shaped route through the Ochil Hills; the event is full with a waiting list.
Trail half marathon around Dalmeny Estate and Cammo Nature Reserve with wooded trails, riverside paths, under 1000 ft total ascent, chip timing and a finisher medal.
A 12 hour night running challenge at Dalkeith Country Park where participants complete repeated 5 km loops solo or in teams to record their total distance.