Trail Running calendar near Cupar 2026-2027

We have found 126 Trailruns within 80 miles of Cupar. See below where and when you can find the races.

A multi-terrain ultra around the Tweed Valley based at Glentress Peel Visitor Centre in mid-November. Two route options, 65 km and 50 km, follow forest trails, riverside paths and open moorland with marked routes and aid stations.

UTMB Index

Part of the South By Five series, this is a free 5km run in Glasgow's Linn Park. It's one of six park events over 12 weeks, with the goal of completing five to finish the series. Entry supports local community and charity projects.

Experience off road trail runs through the Hermitage of Braid and Blackford Hill. With 10km and 5km routes plus a festive 1.2km fun run, participants enjoy marked courses and post race refreshments.

Run a free 5 km in Glasgow's Rouken Glen park as part of the South By Five series. Your participation supports the Acorn Trails Community Fund and a local animal charity. Join for a community focused run and an optional park clean up.

December 2026

Experience a 55 mile winter ultra run through the remote Cheviot hills of Northumberland. This supported loop course provides GPS tracking and a 24 hour limit for experienced runners seeking a true seasonal test.

Experience a festive trail run through the stunning private grounds of Scotland’s historic Glamis Castle. With 1 mile, 5 mile, and 10 mile distances, there is an event for everyone including canicross runners and families.

South By Five is a free 5 km park run series in Glasgow. The Pollok Park event is one of six races held over 12 weeks. Participants can run single events or aim to complete the series.

January 2027

A trail running festival on 3 January 2027 through Glenmore Forest finishing at Loch Morlich beach, offering 5.6 km and 11.2 km races with chip timing, finisher medals, home baking and prizes; dogs are allowed on leads.

This is a single 5km event in Bellahouston Park, part of the wider South By Five series visiting six Glasgow parks. Entry is free but includes a mandatory donation to a community fund. Runners can join just this race or aim to complete the..

Experience a deep winter half marathon to the summit of Hedgehope and back in the Shadowlands Series. This fully marked fell run features challenging weather and terrain for prepared participants.

Experience a trail running festival at Vogrie Country Park featuring multiple distances from a 1.6km fun run to a half marathon through woodlands and the scenic Tyne Valley.

The South By Five series brings a free 5km run to Queens Park in Glasgow. This is a single event in a 12-week series visiting six parks. Entry requires a community donation, with support for a local animal charity.

February 2027

Experience the dramatic Northumberland coastline with this linear trail run through dunes and sandy beaches. Choose from four distances ranging from 10k to Ultra on a fully marked course starting in the historic setting of Bamburgh.

UTMB Index
March 2027

Experience a point to point trail run along the historic Northumberland coast featuring two distances and iconic castle views. Runners enjoy a well supported route ending at the scenic Druridge Bay Country Park.

May 2028

Experience a 34 mile ultra marathon from Perth to Pitlochry as part of the Myths and Legends series. This exclusive event features tracking for all runners and a challenging 4 mph minimum pace requirement.

Experience a 31 mile ultra marathon from Innerleithen to Edinburgh. This single day event features a scenic route with 2,793 feet of ascent and is part of the legendary nine day SCOTIA challenge series.

Experience a 40 mile ultra marathon journeying from Edinburgh Airport to Perth. This single day event features scenic Scottish landscapes and is part of the legendary nine day SCOTIA challenge series.

June 2028

Experience a 39 mile ultra marathon from Kingussie to Inverness as part of the Scottish Myths and Legends series. This single day challenge features a mountainous route and limited participant numbers for an exclusive running experience.