Trail Running calendar near Cupar 2025-2026

We have found 99 Trailruns within 80 miles of Cupar. See below where and when you can find the races.

Explore historic Stirling at the William Wallace Running Festival on 10 October 2026, with mixed terrain routes past Stirling Castle and the Wallace Monument. Distances suit all runners from a fun mile to 50 km and 70 km ultras with relay t..

Take on the Bennachie Ultra Marathon, a scenic yet demanding 50k across Bennachie peaks with over 5000 ft of climb on trails and moorland. Limited pre entry places make this October classic a must for experienced trail runners.

Join the Dramathon along the Speyside Way, running past iconic distilleries and finishing at Glenfiddich. Choose marathon, half, 10km or a four person team relay and celebrate at the finish with a commemorative miniature dram.

Join the Auchterarder 10K Chilli Trail on 31 October for a Halloween themed run through the Ochil Hills with forest trails, stream crossings and plenty of costume fun. All finishers receive a snood and bespoke medal and there are prizes for..

Join Trail Outlaws for the Dark Skies Run at Wooler on Halloween night for 10 km or half marathon trail routes beneath Northumberland's starry skies. Marked trails, stocked checkpoints and a cozy hostel base make for a memorable night run.

Start and finish in Alva Glen and tackle a rugged 14.6 km course with 966 m of ascent through Ochils Woodland Park, summiting Ben Cleuch and The Nebit for sweeping views. Prizes for top finishers and veteran categories add competitive appea..

November 2026

Join Scurry Around Tentsmuir, a trail running festival in scenic Tentsmuir Forest with routes for all abilities and a lively atmosphere. Marked off road trails, medals for key distances, and proceeds benefit local community causes.

Challenge yourself on the Dava Way 50k, a scenic 50 km trail from Grantown on Spey to Forres across woodland, moor and old railway line. Enjoy runnable tracks, summit views and riverside stretches on this classic Scottish ultramarathon.

Take on the John Muir Way Nocturnal Ultra: in six hours run as many 5 km off road laps as you can. Solo or teams of up to three, with a lively basecamp, course support and a headtorch required.

Wooler Trail Races in Northumberland National Park serve up scenic, challenging trail running with marathon, half marathon and a double option. Expect muddy steep climbs, clear course markings and friendly checkpoint support.

Join the Hermitage trail runs for scenic 10km and 5km routes over Blackford Hill plus a festive 1.2km fun run. Kids get elf hats and all enjoy snacks while proceeds support Friends of the Hermitage and Morningside Primary School.

December 2026

Take on the Winter Cheviot Goat, a rugged 55 miles loop across the Cheviots with GPS tracking and a 24 hour limit. Finishers get a t shirt and medal while top runners contest the Edwin Nelson Cup and camping is on site.

Celebrate the season with the Festive Trail Runs at Glamis Castle on 6 December, choose the family 1 mile or scenic 5 and 10 mile trails. All finishers get a bespoke bauble or medal, festive treats and event merch, and dogs are welcome in 5..

May 2028

First edition MTC GRIMALKIN is a 34 mile one day ultra from Travelodge Perth A9 to Atholl Guest House in Pitlochry, part of the Mount to Coast End to End series. Entries are limited and runners are tracked for safety.

Push your limits on the inaugural 31.3 mile MTC GLAISTIG ultra from Innerleithen to Edinburgh Airport as Day 2 of MTC SCOTIA. Limited to 40 starters, all finishers get a bespoke medal and champions receive trophies.

Tackle the MTC Nuckelavee single day 40.1 mile ultra from Edinburgh Airport to Perth on 29 May 2028. With a small field and bespoke medal for finishers, this scenic challenge is perfect for seasoned trail runners seeking a big day out.

June 2028

New for 2028, MTC BEITHIR is a rugged 39 mile ultra from Kingussie to Inverness, the sixth day of the MTC SCOTIA challenge. Limited to just 40 runners, it features real time tracking, safety support and a bespoke finisher medal.