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.

A Welsh randonneuring staple departing from Chepstow, this route begins with a fast, rolling warmup heading north to Hay-on-Wye. After the Hay control, the real work begins: the iconic long climb over Gospel Pass—Wales’ highest road pass. You will be rewarded with a spectacular descent past Capel-y-Ffin, dropping down through Abergavenny and Usk before the return leg to Chepstow. This is a route for the hardy; previous editions have seen everything from glorious sunshine to snow, ice, and strong winds. Please come equipped for the mountains and all possible road conditions!
Event Details:
- Points: 2 AAA Points.
- Controls: 2 Café controls and 3 Info controls.
- Start: HQ offers toilets, tea, coffee, and a breakfast roll to get you fuelled.
- Validation: E-Brevet available.

ENTER via link below

Embark on a breathtaking 216km Audax adventure from Chepstow to conquer the Cheddar Gorge, passing through Bath, Wells, Glastonbury, Cheddar, Chew Valley Lake and Clevedon.
This is an ideal first time 200km Audax with quiet lanes and iconic landmarks. Starting from our Cycling HQ with a free breakfast roll, tea or coffee, you then cycle over the Severn Bridge and around Bristol to take the Bristol & Bath Railway Path to Bath. Then its through the Combe Down Tunnels and on for Breakfast at The Riders Rest. Next its on to Wells and then to climb Glastonbury Tor before taking lunch in the quirkiest town in England. From Glastonbury its easy miles on the Somerset Levels riding to Cheddar. The local Cheddar Scouts Group have backed some cakes for you at the controls to fuel your ascent of the famous Gorge. After the climb we take you past Chew Valley Lake and then on to the seaside town of Clevedon for tea before crossing the Avonmouth and Severn Bridge again for a pub finish in Chepstow. You will need to bring a pen to answer the questions at the 4 information controls.

Trefi Marchnad Cymru (Welsh Market Towns)
Distance: 106km (BP100)
Host: Chepstow Cycling Club
Route Overview: A scenic and easy-to-navigate loop starting and finishing in Chepstow. The route highlights the best of South East Wales, passing through the historic towns of Usk, Abergavenny, and Monmouth, before returning via the picturesque Wye Valley and Tintern.
Start: Coffee@Upcycle HQ. Entry includes a breakfast roll, tea, and coffee.
Controls: 2 x Commercial Controls (Abergavenny & Tintern) + 3 x Info Controls.
Terrain: Beautiful rolling countryside through Monmouthshire.

An excursion into the Cotswolds featuring quiet, pretty lanes and a mostly flat profile, with just one notable challenge: the ascent of Frocester Hill. At 168km (just over 100 miles), this is an ideal first century ride for those looking to push their distance limits.
The Route: Starting with a complimentary breakfast roll, tea, and coffee at Chepstow CC HQ, you will head out over the Severn Bridge into England. From there, quiet lanes lead you to the foot of Frocester Hill. This celebrated climb lifts you from the Severn Valley up towards Nympsfield, rewarding your effort with breathtaking views back toward Wales. After a descent into Nailsworth (Control 1), the route rolls through the picturesque Cotswold Water Park before reaching the historic town of Malmesbury (Control 2), where the High Street offers ample options for lunch. The return leg features a steady climb to the A46, a thrilling descent to Pucklechurch (Info Control), and a final 30km run through Coalpit Heath and Olveston. You finish by crossing the Severn Bridge back into Chepstow.

Key Details:
Distance: 168km (104 miles)
Time Limit: 11h 40m (Generous allowance for all abilities).
Start: Chepstow Cafe@Upcycle (Breakfast included).