Cupar
Trail Running Calendar near Cupar 2026-2027
Explore the top trail runs near Cupar for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
Three evening 5K races around Leith Links, Fettes and Inverleith Park in Edinburgh with chip timing, medals and category prizes; single and series entry options available.
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.
A 5 km trail race at Letham Glen on 13 September 2026 with medals for all finishers, overall and local prizes, on-site facilities and a £10 entry fee.
A beach out and back about 5k on Pettycur Sands with dog running categories, capped at 100 entries and prizes across age and multi dog classes.
A timed track run at Meadowmill where entrants run as many laps as possible to a participant-curated soundtrack, supporting The Junction with cake, junior races and community activities.
October 2026
A pre-entry coastal trail race in Aberdour on 04 Oct 2026, about 4 miles out-and-back along the Fife Coastal Path with medals for all finishers and age-category prizes.
Community charity run and walk in Inverleith Park, Edinburgh on 11 October 2026 offering 10 km, 5 km and accessible 2 km family routes.
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.
Scenic trail half marathon around Dalmeny Estate and Cammo Nature Reserve near Edinburgh, featuring wooded trails, river paths, chip timing and charity support for the RNLI.
A 12-hour night trail challenge at Dalkeith Country Park: complete as many 5 km loops as possible solo or in teams of two or four on marked woodland routes.
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.
A six hour night event where solo runners or teams of up to three complete as many laps as possible on a well marked 5 km off road loop with a tented base, music and lights.
Short Course Cross Country Championships on 7 November 2026 at Kirkcaldy High School with ProTay managing race pack fulfilment and timing alongside scottishathletics.
Approximately 5 miles of trails around Falkland Estate with forest loops, age-category prizes, a race memento and a £14 entry fee; limited to 100 places.