Cupar
Trail Running Calendar near Cupar 2026-2027
Explore the top trail runs near Cupar for 2026-2027! We've gathered 44 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
Up and Running Events holds measured, chip timed 5k, 10k and half marathon races at Holyrood Park, Edinburgh, with hydration stations, marshals and goody bags.
Out and back hill race near Lower Largo on 14 Nov 2026, about 10k with 300 m elevation, held under a Scottish Athletics permit.
FoxTrail Race 1 at Foxlake offers 5 km and 13 km off road trail runs through woodland, farmland and the John Muir Way on 14 November 2026.
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 69 km trail ultra from Glamis Castle to Scone Palace on 28 November 2026 with marked route, checkpoints, GPS tracking, finish medals and a meal voucher for all finishers.
December 2026
Multi-terrain winter trail at Balgone Estate offering 5 km and 18 km courses on mostly flat woodland and farm paths, with series prizes based on best three placings.
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.
Night trail runs at Balgone Estate on 16 January 2027 with 5 km and 10 km routes through woodland and muddy farmland, fully way marked and requiring a head torch.
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
Winter trail races at Harvest Moon Holidays near Tyninghame, offering 5 km and half marathon routes across coastal paths, woodland, farm tracks and a sandy beach with a river crossing.
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.
Backyard Ultra at Dalkeith Country Park with repeated 6.7056 km loops on the hour until one runner completes the final solo loop to become Last One Standing.