Cupar
Trail Running Calendar near Cupar 2026-2027
Explore the top trail runs near Cupar for 2026-2027! We've gathered 40 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
A solo 69 km trail ultra from Glamis Castle to Scone Palace on 28 November 2026 with GPS tracking, checkpoints, finish meal and medals.