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
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.
Beach canicross at Pettycur Sands with an out and back course of just under 5k, capped at 100 entries and categories for adults and children running with dogs.
A charity LP format track event at Meadowmill Sports Centre where entrants run as many laps as possible in a 33.3 minute music set, with kids races, prizes and cake.
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 event in Inverleith Park on 11th October 2026 offering a 2K family run, a 5K cross country run and 5K and 10K walking options.
Eight hour loop challenge at Tentsmuir Forest where runners complete as many 4.367 mile loops as possible, tracked by electronic wristbands.
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.
Trail runs at Hermitage of Braid and Blackford Hill with 10 km, 5 km and a 1.2 km festive fun run supporting a local school and the reserve.