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 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.
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.
November 2026
A mixed terrain trail festival at Tentsmuir Forest near Tayport offering a half marathon, 10 km, 5 km, junior 5 km and a 1.2 km family fun run with marshalled, signposted routes and charitable proceeds for the Tayport Community Trust.