Cupar
Trail Running Calendar near Cupar 2026-2027
Explore the top trail runs near Cupar for 2026-2027! We've gathered 43 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
An 8 hour trail loop challenge at Tentsmuir Forest where runners complete repeated 4.367 mile laps tracked by electronic wrist tags.
A Halloween-themed 10K trail in Auchterarder through the Ochil Hills with varied terrain, goody bag, medals and age-category prizes; online entry, age 16 and over.
Scenic chip timed half marathon near South Queensferry on woodland and coastal trails, with finisher medal and proceeds supporting South Queensferry RNLI.
A 12 hour night trail challenge at Dalkeith Country Park where runners complete repeated 5km loops solo or in teams; entries are closed.
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 runners complete as many 5 km trail loops as possible, solo or in teams of up to three, with a tented base, 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.
A trail race of about 5 miles around Falkland Estate, starting near Strathmiglo Village Hall with forest loops in Drumdreel woods and age category prizes.
A chip-timed event at Holyrood Park in Edinburgh offering 5k, 10k and half marathon distances with race support and on day entries usually available.
Out and back hill race near Lower Largo on 14 Nov 2026, about 10k with 300 m elevation, held under a Scottish Athletics permit.
A small pre-entry trail race at Annsmuir Woods, Ladybank, covering about 4 miles with a 50-runner limit and an entry fee of £11.
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 marked 69 km trail ultra from Glamis Castle to Scone Palace on 28 November 2026 with chip timing, GPS tracking, finish meal and medals for all finishers.
December 2026
January 2027
Winter trail race at Balbirnie Park on 10 January 2027 over 4 to 5 miles of muddy woodland paths with medals for finishers and age-category prizes.
A 10 km winter trail around Bertha Loch and Almondbank in Perth on 31 January 2027 with chip timing, wooden finisher medals, on-site toilets and nearby parking.
February 2027
Timed eight hour loop challenge at Gullane Beach on 27 Feb 2027, with 4.367 mile laps over beach, coast, trail and fields and electronic wristband timing.
March 2027
A 50 km ultra along the John Muir Way through East Lothian coast, towns and trails, starting at Port Seton Promenade and finishing at Foxlake Adventures in Dunbar.