Trail Running calendar near Cupar 2025-2026

We have found 105 Trailruns within 80 miles of Cupar. See below where and when you can find the races.

The Enchanted Ultra 50K is a challenging ultra-marathon held in the rugged Cheviot Hills near Wooler, United Kingdom. This 50-kilometer race offers a unique adventure through ancient forests, mystical bogs, and scenic valleys, requiring participants to navigate using GPS along a digital route. The c..

The Glenmore 24 Trail Race is a challenging 12- or 24-hour trail running event held in the scenic Glenmore Forest near Aviemore in the Scottish Highlands. The course features a 4-mile loop starting at the Hayfield, winding through forest trails and passing Loch Morlich, offering a fully off-road exp..

The Cove & Kilcreggan 10K is a scenic and challenging running and walking event held on the picturesque peninsula near Helensburgh, Scotland. Scheduled for September 7, 2025, the event features a 10K run and walk starting and finishing at Cove Burgh Hall. The course includes mixed terrain, beginning..

The River Ayr Way Ultra Marathon is a challenging 40-mile race set against the stunning backdrop of Ayrshire, Scotland. Participants will traverse a mix of off-road rural paths and quiet roads, with checkpoints every 10 miles offering refreshments and support. The event includes a relay option, allo..

Tom’s Cairn 10K & 5K Trail Races take place at Finzean Church, Scotland, starting and finishing at Birse and Feughside Parish Church. The 10K course features a scenic trail through Finzean Woods, a climb to the summit of the local landmark Tom's Cairn, and a fast descent back to the church, mostly w..

Pilgrims’ Ultra is an ultramarathon event held in Northumberland, starting from Holy Island and featuring three distance options: 50k, 100k, and 100 miles. The race follows the scenic St Oswald's Way route, showcasing Northumberland’s coastline, islands, castles, countryside, river valleys, hills, v..

The Run of the Mill is a challenging 14.6 km race with 966 meters of ascent, held in Alva Glen near the Ochils Woodland Park in Clackmannanshire, Scotland. The course starts and finishes at Alva Glen, passing through scenic footpaths to Tillicoultry and ascending several summits including Andrew Gan..

The Highland Fling Race is a 53-mile (85 km) ultra trail marathon held annually in Scotland, traversing the southern section of the iconic West Highland Way through Loch Lomond & the Trossachs National Park. The point-to-point course runs from Milngavie near Glasgow to the village of Tyndrum, featur..

UTMB Index

The Arrochar 10k is a scenic and varied terrain race held in Arrochar, Argyll, Scotland. The 10-kilometer course features a mix of track, forest roads, and paths, including a significant hill offering views over Loch Long. Runners cross the A83 trunk road with marshals' guidance and finish alongside..

The Two Breweries Hill Race is an annual running event held in the scenic Scottish Borders, covering a challenging 30 km (18 miles) route with an ascent of 1500m (4900ft). Starting at Traquair House and finishing at Broughton Ales, the race celebrates local breweries and the spirit of hill running...

The Wild Deer Scottish Trail Runs at Dalkeith Country Park, near Edinburgh, offer a variety of trail running distances including 5km, 10km, half marathon, marathon, and a 32.5-mile ultra. Set within a historic 1000-acre estate, the courses feature mixed terrain with rough trails, firm and grass path..

The TriWorks Floors Castle Trail Race, held on September 28, 2025, takes place in the scenic Scottish Borders at Floors Castle, Scotland's largest inhabited castle. The event offers three trail running distances: a 10km race (two laps of a 5km course), a 5km race (one lap), and a Junior 3km race for..

October 2025

The Aviemore Half Marathon and 10k Race For All take place at Badaguish Outdoor Centre near Aviemore, Scotland, set against the stunning Cairngorms backdrop. Both races start and finish at Badaguish, featuring scenic routes through Glenmore Forest Park with forest tracks, loch shores, and mountain v..

The Glasgow to Edinburgh Ultra is a 57-mile ultra marathon starting at Glasgow's Riverside Museum and finishing at Edinburgh Athletics Track. The course is predominantly flat and fast-paced, following canal towpaths, tarmac, and concrete paths, passing landmarks like the Falkirk Wheel and the Antoni..

UTMB Index

The Bennachie Ultra Marathon is a challenging 50k (31-mile) trail race held in the Bennachie Hills, North East Scotland, starting and finishing at the Bennachie Visitor Centre. The course features over 5,000 feet of elevation gain and traverses six prominent peaks, including Mither Tap, Oxen Craig,..

The Manor Water Hill Race, organized by Carnethy Hill Running Club, is a challenging 9.3-mile (15 km) hill running event held near Peebles, Scotland. Featuring 2,130 feet (650 meters) of ascent, the race starts near Woodhouse Farm in the Manor Valley and follows a scenic route along the John Buchan..

The William Wallace Running Festival, held in Stirling, Scotland, offers runners a chance to "follow in the footsteps of legends" across historic battlefields and scenic countryside. The event features multiple race distances: a challenging 70km ultra marathon and a 50km ultra marathon, both availab..

The Carnethy Skyloop is a challenging hill race organized by the Carnethy Hill Running Club in Midlothian, Scotland. Covering approximately 16 miles with a total ascent of 6,200 feet, the race offers a demanding course through the scenic Pentland Hills. The event starts and finishes at the Lothianbu..

The Dramathon is a unique trail running event held in the scenic Speyside region of Scotland, featuring marathon, half-marathon, 10K, and relay race options. The courses follow the Speyside Way, primarily along old railway lines and forest tracks, passing several renowned whisky distilleries includi..

The Tentsmuir Forest 8-hour Challenge, organized by NU Limits Running, is an endurance running event held in Tentsmuir Forest, Scotland. Participants aim to complete as many 4.366-mile trail loops as possible within an 8-hour time limit, with each lap featuring 85 feet of ascent. Completing 3 laps e..