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.
September 2026
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.
Trail running festival at Dalkeith Country Park offering family, 5 km, 10 km, half, marathon and ultra distances, canicross friendly with live chip timing.
October 2026
An approximately 4 mile out and back trail on the Fife Coastal Path at Silver Sands, Aberdour, with sea views, medals for 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.
A Category A long hill race of about 30 kilometres and 1,700 metres ascent in the Pentland Hills, with unmarked navigation and multiple checkpoints.
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 October trail half marathon around Dalmeny Estate and Cammo Nature Reserve featuring wooded trails, riverside paths and farm tracks, with proceeds supporting South Queensferry 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 nocturnal event on a well marked 5 km trail loop, with solo and three-person relay options, a tented base each lap, music, lights and food.
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.
Out and back hill race on 14 Nov 2026 near Lower Largo, about 10 km with over 300 m ascent, organised by Anster Haddies; toilets at the Crusoe Hotel and trail shoes recommended.
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.
December 2026
February 2027
Experience a scenic 10km trail run around Bertha Loch and the River Almond featuring technical wooded paths and handmade medals for all finishers.