Trail Running calendar near Cupar 2025-2026

We have found 74 Trailruns within 80 miles of Cupar. See below where and when you can find the races.

Get race ready for the Illuminator with a coached social headtorch trail session on 15 October 2025. Bring your own headtorch for this inclusive one hour practice and book with Meryl Cooper Coaching.

Event overview EpicTrails 10km - Exploring trails by headtorch is a night trail run set for 16 October 2025, starting from Milngavie Train Station, G62 8PG. The route explores local trails including sections of the Clyde Coastal Path and th..

Event overview The Dramathon takes place on 17-18 October 2025, with the main races organised for 18 October. All race distances were sold out as of 11 January; waiting lists are open for some events. The finish line for all races is at Gle..

Push your limits at the Tentsmuir Forest 8 hour Challenge in Tayport. Run as many 4.366 mile trail loops as you can in eight hours on scenic forest paths and chase half marathon, marathon or ultra distances.

Event overview The Millstone Hill Race takes place on 19 October 2025 and starts and finishes at the Bennachie Visitor Centre car park. The course is an approximate 10 km hill route with 360 m of elevation on mixed terrain. The route will h..

Ladybank Nuts Trail Race is a small, friendly event for all abilities held at Annsmuir Woods, Ladybank, Fife (Race HQ: Ladybank Youth Club, Beeches, KY15 7LR). The course is about 4 miles, run as two flat laps on woodland trails and grass p..

Kippen Trail Race is a 5-mile trail run held in Kippen, Scotland (FK8 3EQ). The route is mostly off-road on trails around the village, with a short section on a quiet road, starting from the football pavilion at the sports field. The course..

Event overview EpicTrails 8km is a headtorch trail run on 23 October 2025 that sets off from Milngavie Train Station (G62 8PG). The route uses local trails including the Clyde Coastal Path and the West Highland Way, and includes other nearb..

Dark Skies Run @ Wooler : overview The Dark Skies Run at Wooler is organised by Trail Outlaws. The next scheduled race date is 25/10/2025. The event takes place at Wooler Youth Hostel, 30 Cheviot Street, Wooler, Northumberland, NE71 6LW. Th..

Take on the classic Meall a'Bhuachaille hill race near Aviemore, a challenging 13 km route with 720 m of climb across open ridge and forest tracks. Expect rugged terrain, stunning summit views and mandatory mountain kit on this scenic Cairn..

Tackle the scenic Jedburgh Three Peaks 38 mile trail ultramarathon around historic Jedburgh on 25 October 2025, fully waymarked with live timing and checkpoints. Relay teams welcome and all finishers receive medals and goody bags.

Duncan Macfarlane Race "The Dunky" : event overview The Duncan Macfarlane Race, also called "The Dunky", takes place on 26 October 2025 at Mugdock Country Park, Milngavie, East Dunbartonshire, United Kingdom. The event i..

The Wooler Trail Races, held in Wooler, Northumberland, offer runners a challenging experience in the heart of Northumberland National Park. Participants can choose between a trail marathon and a half marathon, with an option to complete bo..

November 2025

Tinto Hill Race (senior) The race is an A-category short hill race organised by Carnethy Hill Running Club. The course is 4.4 miles long with about 1500 feet of ascent and follows an unmarked route that crosses ground above 2000 feet. Entry..

Take on a scenic 33 miles through Perthshire in the Glen Ogle 33, passing the Falls of Dochert and the iconic Glen Ogle Viaduct. Limited to 400 runners, this autumn ultra pairs sweeping Highland views with a true trail challenge.

Take on the Auchterarder 10K Chilli Trail into the Ochil Hills with forest trails, stream crossings and steep ups and downs. Ages 16 plus, the friendly event welcomes all paces and gives every finisher a bespoke medal and snood.

Bridge of Orchy 10k is a 10-kilometre multi-terrain race in Bridge of Orchy, Scotland, set along the scenic West Highland Way. The course begins at the bridge with a demanding 2 km climb to Loch Tulla, then a fast road section from Inverora..

Scurry Around Tentsmuir Forest Trail Running Festival 2025 : event details Scurry Around Tentsmuir Forest is a trail running festival held on 02 Nov 2025 at the Larick Centre, Tayport. The festival offers mixed-terrain, clearly marked and m..

Seven cross country races across the Scottish Borders from November to March, with junior and senior events at each venue. Join the series for a full season of mud, camaraderie and competition with chip fitted bibs mailed before race one.

Event overview The John Muir Way Nocturnal Ultra Marathon takes place on 08 Nov 2025 at the John Muir Way - Balgone Estate, Balgone Barns, North Berwick EH39 5NY. Runners have six hours to complete as many laps as possible of a well-marked..