Prepare for a true late-winter test. This route tackles several breathtaking long climbs to earn you 3.5 AAA points. You will face the steep side of the Gospel Pass, The Tumble, and finally, "The Darkside" of Wentwood. The ride departs Chepstow up the Wye Valley, passing Tintern Abbey and Monmouth. The legs get their first test past Rockfield and Newcastle, followed by a sharp kick up to Grosmont and the first control at Hope’s Shop (Longtown). Next, you face a steady climb to Hay-on-Wye, passing through Clyro and up to Paincastle. Refuel at Erwood Station before the main event: the Gospel Pass via Sustrans Route 42. Be warned: this section is fully exposed to the elements—expect wind, rain, or snow. A long descent leads to Abergavenny for an Open Control, immediately followed by the ascent of the mighty Tumble. Enjoy a flatter, faster run to Usk along the river before the final sting in the tail: The Darkside of Wentwood. After a fast descent to the final Info Control at Caerwent, it’s a run along the A48 back to Chepstow for the Arrivée and a well-earned pint at The Three Tuns Inn.

Important: Pack plenty of layers! You will ascend over 500m twice in potentially harsh winter conditions.

Points: 3.5 AAA

Facilities: Start HQ offers breakfast rolls, tea, coffee, and toilets.