Cupar
Trail Running Calendar near Cupar 2026-2027
Explore the top trail runs near Cupar for 2026-2027! We've gathered 37 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A new up and down hill race at the Kinross Show on 8 August 2026 with a mostly pathless 2.3 mile route, 750 ft ascent and included show access.
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 10 km marked trail around Bertha Loch and Almondbank with technical and muddy sections, woodland terrain and handcrafted finisher medals. Routes change by season and the August run accompanies a 12 hour lapped event.
A 12 hour trail challenge on a 10 km loop around Bertha Loch where runners go solo or in teams. The event features chip timing with live results, water on course, medics, marked marshalled trails, prizes and medals for finishers.
A 5.7 mile trail race in Cardenden Woods on 23 August 2026 that passes the site of Scotland's last pistol duel from 1826. Mainly off road with muddy, rocky and rooted sections; medals for all finishers and cash prizes for top placings.
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 5 km loop at Dunnikier Park in Kirkcaldy over mixed surfaces, run under Scottish Athletics permit with a one hour time limit and fundraising support for Maggie's Fife.
A two person relay on 30 Aug 2026 using Fife's half marathon route through parks, coastal path and the waterfront with a three hour time limit.
A beach race on 30 August 2026, licensed by Scottish Athletics, covering about 4 miles on sand at low tide. Entries are limited and proceeds support Towerbank Primary School and other local 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.
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 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 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 on a 5 km loop at Dalkeith Country Park with solo and team relay options and mandatory headtorch and trail footwear.