A thousand years of England, one lane at a time.
In the Middle Ages, wool from Cotswold sheep was the finest in Europe. The money built honey-coloured market towns and churches far grander than their villages. When the trade faded, the Cotswolds were left almost as they were. Your guide brings the stories. You just ride.
“I thank God and ever shall, it was the sheep that paid for it all.”An old wool merchant’s rhyme
- Quiet lanes between honey-coloured villages, with hardly a car
- Stow, the Slaughters and Bourton-on-the-Water in one day
- A painted Judgement Day hidden in the woods
- Train from Paddington and home again, no car needed
Hills, water and the quiet way home.
A storyteller on a bike
Every Wayside ride is led by an experienced cycling guide, trained in ride leadership and first aid, who has ridden every mile of the route before you arrive.
They set an easy pace, sort out the train times and know which pub does the best lunch. Most of all, they know the stories: who built it, who fought over it and why it matters.
Gentle, with plenty of stops
About 22 miles over a full day, with a few gentle climbs. We ride together at a sociable pace, with time to look around at every stop. E-bikes are available if you’d like a hand on the hills.
Bring yours, or borrow ours
Bring your bike on the train, or we’ll have one waiting at Kingham. Everyone rides together.
Hire includes a helmet and is waiting for you at Kingham.
- A guide and storyteller with you all day
- A hand-picked route on the quietest lanes, ridden and checked before you arrive
- A small group at a sociable pace, with nobody left behind
- Coffee and snacks at our stops
- Everything sorted, from the best train to catch to where to stop for lunch
- Train fare
- Lunch, so eat where you like or bring your own
- Drinks with lunch
Direct train from London Paddington to Kingham, about an hour and a half.
Back to Kingham for the train home, the same way.
Dates and booking. Bookings open 1st January.
Rides run from March 2027, on regular dates through the year or as a private ride for your own group. Leave your details and we’ll remind you when bookings open.