Trail Running calendar near Cupar 2025-2026

Take on the iconic West Highland Way Race, a 96 mile ultra from Milngavie to Fort William through stunning Scottish Highlands. This epic overnight challenge offers 35 hours to finish and a mountain finish at the Nevis Centre.

The Fellrunner at Windy Gyle is a rugged 13.7 km test with 549 m of climb across scenic Northumberland hills on Sun 21 Jun 2026. Entry on the day is welcome with modest fees for members and non members.

Tackle the classic 20 mile Chevy Chase across wild Northumberland, summiting Cheviot and Hedgehope on an unmarked upland route that requires map and compass navigation. Finish in Wooler with food, T shirts and prizes.

Tackle a tough 15 km hill challenge with 960 m of climbing at Dollar Academy in Central Scotland on Sat 4 Jul 2026. Expect steep, rewarding climbs, lively team competition and easy entry online or on the day.

Run Edinburgh's seven hilltops in a mixed road, trail and hill event that blends urban navigation with racing. Choose your own route between hilltop checkpoints and opt for the competitive Race or the more relaxed Challenge.

Take on the wild Northumberland hills at the Saint Cuthbert's Way Ultra in Wooler, with UTMB qualifying 100KM and 45M distances. Fully way marked route includes a tide race section, stocked checkpoints, recce runs and live GPS tracking.

Take on the British Championship Hill Race at the Alva Games in Scotland. A short 2.5 km course climbs 365 m through steep slopes, gorse and muddy gullies, with junior and senior categories for a proper hill running test.

Tackle scenic hills and a sweeping downhill in the Moffat Festival of Running on 14 July 2026, featuring a 15 km mixed terrain race plus junior and tots events. Expect tough climbs, great views and local prizes for runners of all ages.

Run the Blades is a summer weekend of trails among towering turbines at Whitelee Wind Farm. Pick 10K, half marathon, 50K or junior mile and celebrate at the Event Village at Turbine 53 with prizes and a spinning medal.

Scurry to the Sea 2026 is a scenic mixed terrain challenge of just under 12 miles, starting on Allermuir Hill and finishing on Musselburgh harbour beach with a sandy finale. Limited to 275 places and advance entry only, it blends cross coun..

Experience traditional Highland Games with tossing the caber, piping, Highland dancing and fairground fun at Newtonmore on Saturday 1 August 2026. Test yourself on the Creag Dhubh Hill Race a rugged 4½ mile climb with about 1200 feet ascent..

Tackle the rugged Ochil 2000s in Stirling on 22 August 2026, a classic fell run across Central Scotland offering about 20 miles and 5400 feet of climbing. Expect spectacular views and testing terrain for experienced runners.

Join the Eyemouth Twilight 5k on 28 August 2026 for a chip timed coastal evening run with medals for finishers. Family friendly Scott's Mini Fun Runs, goodie bags and Giacopazzi's Gelato at the finish make it a fun seaside outing.

The Highland Fling Ultramarathon is a scenic point to point 53 mile trail from Milngavie to Tyndrum through Loch Lomond and the Trossachs. Expect tough climbs, wild views and a lively finish with food, massage and live timing.

Join Maverick Kielder Forest Gravel on 5 September 2026 for scenic forest runs from 5 km to 52 km suitable for all abilities. Fast trails, steady climbs, weekend camping and refill stations for reusable bottles make it a weekend adventure.

Run the scenic River Ayr Way, a 44 mile source to sea trail through wildlife rich valleys and historic sites. Every September the River Ayr Way Challenge invites runners to tackle a 40 mile ultra for a memorable weekend adventure.

Tackle the Enchanted Ultra 50K, a scenic trail ultramarathon through the wild Cheviot Hills around Wooler on 19 September 2026. Expect rugged paths, sweeping views of ancient hillforts and ridgelines, stocked aid stations and a warm finish..

Pilgrims’ Ultra is a scenic ultramarathon on Saturday 26 September 2026, following St Oswalds Way from Holy Island toward Hadrian's Wall past castles, beaches and rolling hills. Choose 50k, 100k or 100 mile distances and finishers receive a..

Enjoy scenic woodland trails at Dalkeith Country Park on 27 September 2026 with routes from a family mile to ultra, welcoming runners and dogs alike. Live chip timing, medals, event merch and an energy bar for every finisher.

Tackle the scenic Glasgow to Edinburgh Ultra, a 57 mile point to point run along canals and towpaths passing the Falkirk Wheel and Antonine Wall. Limited to 750 runners, this on October 10 2026 challenge blends history, scenery and enduranc..