Wayside Rides
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Canterbury Cathedral’s great tower rising above the city
WEEKENDER · TWO DAYS IN KENT

The Canterbury Tales

Two thousand years of arrivals on the coast of Kent

LENGTH
2 days
DISTANCE
About 49 miles
TERRAIN
Mostly flat
ROUTE
Whitstable to Deal
GROUP
Up to 12
PRICE
Coming soon
Keep me posted
THE WEEKEND

England came in through the front door.

For two thousand years, almost everyone who changed the country came ashore on this coast: Caesar, the Romans, St Augustine and, later, pilgrims from all over Europe heading for Becket’s shrine. Then the traffic turned round and Henry VIII lined the shore with castles to keep everyone else out. Your guide brings the stories. You just ride.

WHY YOU’LL LOVE IT
  • Finish the first day at Canterbury Cathedral, in time for evensong
  • Stand where the Romans came ashore, inside walls nearly 2,000 years old
  • Flat, quiet lanes across the marshes, with the sea never far away
  • Train from St Pancras and home again, no car needed
THE ROUTE · ABOUT 49 MILES OVER TWO DAYS
Sketch map, not for navigation
The Thames Estuary Zz Whitstable start Herne Bay Reculver Towers Herne Windmill Fordwich Canterbury overnight Wickhambreaux Richborough Sandwich Deal finish Day 1Day 2 N
DAY BY DAY

Two days, two thousand years.

Canterbury Cathedral in early light, seen across the rooftops and trees
DAY 1 · SATURDAY · ABOUT 24 MILES

Oyster boats to evensong

Start with salt in the air and oysters in the harbour. Along the way there’s a Roman fort half swallowed by the sea, a town of a few hundred people with its own mayor and, as the bells ring for evensong, the cathedral where four knights cut down an archbishop. Today follows our Pilgrims’ Road Jaunt.

Overnight in Canterbury
The gatehouse and round walls of Deal Castle
DAY 2 · SUNDAY · ABOUT 25 MILES

Marshes, Romans and a Tudor rose

Sunday is flat and quiet. Ride across the marshes to where Rome began its conquest of Britain, through a port the sea walked away from and on to a castle shaped like a Tudor rose, on the beach where Caesar is thought to have waded ashore.

Trains home from Deal
WHERE YOU’LL STAY
Timber-framed weavers’ houses leaning over the River Stour in Canterbury

A night in old Canterbury

A comfortable hotel inside the city walls, a short walk from the cathedral. Breakfast is included and your bags will be waiting when you arrive.

YOUR GUIDE

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.

Bring yours, or borrow ours

Bring your own bike, or we’ll have one waiting for you in Whitstable. Everyone rides together.

The weekend, with your own bikePrice coming soon
Bike or e-bike hireAvailable, prices on request

Hire includes a helmet and lock for both days.

INCLUDED
  • A guide and storyteller with you all weekend
  • 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
  • A night in Canterbury, with breakfast
  • Your luggage taken ahead to the hotel
  • Everything sorted, from the best train to catch to where to stop for lunch
NOT INCLUDED
  • Train fare
  • Dinner on Saturday
  • Lunch, so eat where you like or bring your own
  • Drinks with lunch
  • Cathedral entry (evensong is free)
GETTING THERE
Saturday morning

High-speed train from London St Pancras to Whitstable, about an hour and a quarter.

Sunday afternoon

Direct train from Deal back to St Pancras, in under an hour and a half.

Dates and booking. From March 2027.

Weekends from spring to autumn, or as a private ride for your own group. Leave your details and we’ll let you know as soon as dates go on sale.