The Wye Valley Challenge

This epic three-day challenge covers 137 miles, and includes some blood-pumping Cat 3, 4 and 5 climbs in the Wye Valley to test your calf muscles. You’ll start out from Tetbury, crossing over into the stunning Wye Valley, whose terrain ranges from the Herefordshire lowlands (whose soft sandstone accounts for the meanderings of the river Wye) to the dramatic limestone gorges around Chepstow, before heading back into The Cotswolds – staying at our family-owned sister hotels, The Beaufort in Chepstow and The Riverside in Monmouth, en route.

Day 1, Tetbury to Chepstow

Arrive Tetbury mid-morning, and receive detailed cycling notes on the whole break, plus hotel vouchers for our sister hotels in Chepstow and Monmouth. There’ll be time for a quick look around historic Tetbury before a carb-loading lunch sets you up for your 40-mile ride to Chepstow, a picturesque route with some gentle inclines as a warm-up to the more challenging hills to come.

The highlight of this ride is probably when you drop down from The Cotswolds and see the Severn Bridge in front of you, with its two-mile span over the estuary. As this is the strongest tidal estuary in Europe and the birthplace of the Severn Bore, one of Britain’s few truly spectacular natural phenomena, it’s worth pausing to check out the tide: the tidal range here, the 2nd highest in the world, is up to 50 feet/15.4m.

You should arrive at the Beaufort Hotel in Chepstow in time to shower and visit some of town’s historic sites, such as its famous castle, the oldest surviving post-Roman stone fortification in Britain.

Day 2, Chepstow to Monmouth

The dramatic Welsh valleys make this a scenic and enjoyable 45-mile ride, with the serpentine route to Monmouth passing through the breathtaking Usk Valley before dropping down to the Wye Valley, and your overnight stay at the Riverside Hotel in Monmouth.

Day 3, Monmouth to Tetbury

You should be nicely warmed-up now, ready for this, the most challenging leg of ‘The Wye Valley Challenge’. Combining mileage and climbs, including a couple of Cat 4 and one Cat 5 climb, this four-hour, 65-mile route will really test your mettle.

Once you’ve broken the back of this ride and are up on the Wold, stop and have a well-earned breather while contemplating the glorious views over the Severn Basin, which, on a clear day, will extend all the way to the Severn Bridge (‘Been there. Done that.’).

If all goes well, you should be back in Tetbury downing your final complimentary SIS Recovery™ drink by mid-afternoon, when it’ll be time to relax and perhaps have a long hot soak before meeting up with your fellow riders for a well-deserved dinner and a few celebratory drinks to toast your completion of The Wye Valley Challenge.

A mid-week Challenge (Sunday-Thursday) is £299 per person, based on a standard room, and a weekend Challenge (Thursday-Saturday) is £399 per person, based on a standard room. If you’re doing the Challenge with friends, you can save significantly by sharing a double or twin room: check out the prices here.


If you are interested in taking part in the Wye Valley Challenge, please complete the form below.

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