Canterbury Short Break: Walks, Wine and Ancient Wonders in Rural Kent

The North Downs Way runs between Farnham and Dover, tracing a high chalk ridge overlooking the Weald. En route, it passes through some of England’s most appealing scenes, a mix of rolling hills, oak, ash and beech woods, apple orchards, hop fields, heritage sites, holy places – and venerable Canterbury, a city that has attracted walkers for centuries.

Located in the far south-east, Canterbury is home to one of the country’s oldest cathedrals and the shrine of archbishop Thomas Beckett, murdered here in 1170 – pilgrims have flocked here ever since. Today, this lively university city boasts some of England’s finest medieval architecture, as well as wildlife-filled parks, fascinating museums and plenty of places to sample the excellent local produce – from fresh veg and real ales to Whitstable oysters. There are also, of course, lots of opportunities for exploring on foot, with trails leading around the walled city, along the riverbanks and out into the enticing Kentish countryside.

Tour Overview

The icons below highlight the distance, difficulty and theme of this itinerary.




Walks from 5km to 16km




Rolling Countryside / Connecting Villages & Towns / City Exploring


History / Food & Drink / Pilgrimage

Activities & Experiences

Walking / Heritage

Canterbury Short Break: Walks, Wine and Ancient Wonders in Rural Kent

Here’s everything you need to help you plan your very own walking and exploring break in Canterbury and the North Downs. Click on the blue arrow tabs below for more information. To save this itinerary to view later, use the Save to My Rucksack button at the top of the page.

Tour details

This itinerary is being operated by Compass Holidays, who specialise in walking, cycling and activity short breaks and holidays in a variety of UK, European and worldwide destinations.

With more than 30 years’ experience, Compass Holidays allow you to get under the skin of the history, culture and natural beauty of some of the world’s most iconic and spectacular locations.

Compass will arrange your whole tour: you just need to arrange transport to your first location.


  • Accommodation at the stated category with breakfast.
  • Luggage transfers (if applicable).
  • Full tour pack.
  • Smartphone app with GPS routes.
  • 24-hour emergency helpline.

NOT INCLUDED: Lunch, dinner and drinks; entrance to attractions; buses and/or ferries unless otherwise stated; tourist taxes where applicable.


This self-guided short break, based in Canterbury, includes three circular walks, using sections of the North Downs Way and other paths to open up the region’s rich history, delightful countryside and delicious food and drink. The trip is very flexible: choose to stay for two, three or four nights; the itinerary below is a suggestion.

Historic Canterbury is only an hour by train from London. Explore its warren of medieval streets, still part-enclosed within ancient walls and centred on the magnificent Cathedral, Mother Church of the Church of England. There are plenty of cosy old pubs where you can find a good Kentish supper too.

Overnight in Canterbury.



Start by striding out into the quiet countryside to the east of the city. Using sections of the North Downs Way, make a circuit via Bekesbourne and Littlebourne, connecting a series of old villages, each with an ancient church, many with inviting pubs. There are a few gentle hills but generally it’s easy going as you stroll between rippling fields and cattle pasture, pretty thatched cottages and shady woodland.

Walk: 16.3km (shorter options available). Overnight in Canterbury.

Winsome riverside Chartham, with its village green, medieval church and old paper mill,

is only a short bus or train ride from Canterbury, and a lovely start-point for a circular stroll, using stretches of the Stour Valley Walk and the North Downs Way.

From the village, follow the river, trace woodland paths and enter No-Man’s Orchard, the first community-run orchard in the country. You’ll also pass the tempting vines of award-winning Chartham Vineyard – pop into the on-site shop (open on Saturdays) for a free tasting and a chance to buy wine straight from the cellar door.

Walk: 8km. Overnight in Canterbury.

Today, stay in the city and explore its most creative corners by following the Canterbury Sculpture Trail. This route moves you around and about the old streets, riverside paths, peaceful parks and lesser-visited outer edges via a range of diverse artworks – some fashioned into handy rest-stops, others depicting important figures from the city’s past. Look out for the bronze ‘Chaucer in Canterbury’ and sunken ‘Alluvia’, a creation of resin and glass that lies on the bed of the Great Stour.

Walk: 5km. Overnight in Canterbury or return home.


This short break is based in Canterbury, using either a three-star B&B, hotel or inn.

Food & Drink

Canterbury has plenty of choice when it comes to eating out, offering everything from fine dining and gastro pubs to independent cafes and delis. Look out for Kent wines, craft beers and local-caught seafood – especially oysters from nearby Whitstable.


The grade of this tour is moderate, with rolling hills and some steeper sections.

  • Canterbury circular via Bekesbourne and Littlebourne, 16.3km (shorter routes available)
  • Chartham circular, 8km
  • Canterbury Sculpture Trail, 5km


There are a variety of places to visit along the route. We have picked out the highlights and can arrange entry/tickets for customers as required.

  • Canterbury Cathedral – One of the oldest Christian structures in England; pilgrims have made their way here since the Middle Ages, and it remains a working, living church.
  • St Augustine’s Abbey – Tranquil ruins just outside the city walls, originally created as a burial place for the Anglo-Saxon kings of Kent; part of the Canterbury World Heritage Site, along with the Cathedral and St Martin’s Church.
  • Chartham Vineyard – Family-run producer of award-winning wines; vineyard shop offers free tastings on Saturdays.
  • Westgate Parks – Park comprising four distinct areas: Westgate Gardens, Tannery Field, Toddler’s Cove and Bingley Island Local Nature Reserve; the River Great Stour runs through the centre.


Canterbury West is a Grade II-listed railway station, on the Southeastern Rail line. There are regular services from London Charing Cross and London St Pancras International, with the journey taking around an hour. London Victoria and St Pancras International also run services to Canterbury East Railway Station.

The area is served by excellent roads. The M2 motorway provides fast, easy access.


The grade of this tour is moderate. It is available from April until October.

The correct clothes are important to ensure comfort during each walk. We suggest avoiding anything with seams and buttons in sensitive areas. Clothing should take moisture from the body to the outside. Sweatshirts, thin pullovers, and breathable jackets are ideal companions during the cooler days. Take light, waterproof jackets and trousers in case there is rain. On hot days we suggest a cap or hat and sunglasses to protect from the sun.

We advise that you check opening times and booking restrictions before travelling.

Please check out these links for latest advice when in the countryside

Countryside Code

COVID-19 Guidance

Interactive Map

Click here to access the interactive map

Maps, Guidebooks & Merchandise

The official guidebook and map for the Trail are available from the National Trails Shop along with a wide range of gifts and other merchandise.