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Canterbury to Dover – A Long Weekend in Kent With a Difference

Looking for a fun getaway in Kent? This route from Canterbury to Dover shows you all the highlights, including historic architecture, great local restaurants and some of England’s most picturesque countryside.

One of the greatest things to come out of the last 12 months has been a heightened appreciation for what we have on our doorsteps. The stunning countryside, buzzy towns and great places to eat have been there all along, but we’ve really started to notice them, and realise just how lucky we are to live where we do.

north downs way
Ready to explore the stunning North Downs Way?

Whether you’re based in Kent already, or are simply looking to plan a British staycation with a nice varied itinerary, this route from Canterbury to Dover offers a lot. You’ll start in the cathedral city of Canterbury, then venture to the picturesque Kentish village of Chilham, before heading to the quaint fishing town of Whitstable. After that, it’s time to head south towards Dover, with a pitstop in the cute village of Shepherdswell, before relaxing with a view of those iconic white cliffs.

So many colourful beach huts
So many colourful beach huts in Whitstable

This route through Kent gives you the chance to immerse yourself in whatever interests you. Enjoy history? There are plenty of historic buildings to admire, particularly in Canterbury and Dover. Love food? You’ll be in your element as you scoff fresh oysters on the pebble beach in Whitstable or feast your way around The Goods Shed in Canterbury.

If you’re a countryside lover, you’ll fall in love with the walking and cycling routes which take you along the North Downs Way. If you’re not familiar with it, this impressive trail is one of a handful of national trails in Britain. It stretches for a whopping 153 miles, all the way from Farnham in Surrey to Dover in Kent.

north downs way
There are plenty of great opportunities to get out and explore the North Downs Way

While this itinerary works well as a 4-day experience, one of my favourite things about this route is that you could break it up into smaller sections, easily covered on a day trip or two.

Another great aspect is that you can walk and cycle a lot of the route if you fancy, or hop on a train if you don’t! Many of the journeys allow you to tread the historic paths of the Pilgrim’s Way and the Via Francigena. I guess you could consider this a special pilgrimage of your own!

So, while you grab your diary and start plotting exactly when you’re going to head to the Garden of England, I’ll give you a rundown of a few of the highlights, how to get around and tips on how to make the most of your trip.

Canterbury to Dover: A 4-Day Itinerary

Day 1: Canterbury

What to do in Canterbury

Canterbury is a melting pot of old and new. The stunning cathedral dates back to the 11th century and has many a story to tell. Meanwhile, in amongst the ancient, crooked buildings dotted around the city, there are vibrant restaurants, independent shops and even micropubs and breweries.

shopping streets in canterbury kent
I love the shopping streets in Canterbury, Kent

The best way to get to know Canterbury and kick off your long weekend in style, is on a guided tour of the city. You’ll learn all about the history of this amazing place, why it was put on the map so long ago and all about the paths of pilgrims.

There really is so much to see in Canterbury, including the remains of a medieval Dominican monastery (Blackfriars), a medieval castle (Canterbury Castle), an impressive 14th century gatehouse (Westgate), the oldest school in Britain (King’s School) and the oldest church in Britain still in use (St Martin Church).

crooked house canterbury
Crooked house in Canterbury – so much character to this city

This might all sound a little heavy on history, but you really don’t have to be a history buff to appreciate what you’re seeing as you walk around.

Canterbury Cathedral is one of the main attractions, so don’t forget to pop inside and see the shrine of Thomas Becket before you leave.

canterbury cathedral
Canterbury Cathedral at night – what a sight!

Where to eat and drink in Canterbury

To get to grips with Canterbury’s independent spirit, I’d recommend an evening tasting local gins and beers at the Foundry Brew Pub. This unique craft brewery, distillery, restaurant and bar is located close to the high street.

As you drink your way through the pub’s 16 ales, lagers and ciders and 9 spirits, take a moment to appreciate the fact they were all created on site. The Foundry serves great pub food too, using ingredients from local butchers, fishmongers, greengrocers and bakers where possible.

the goods shed canterbury
The Goods Shed is a great place to eat and drink in Canterbury

The Goods Shed in Canterbury is another great spot to eat and drink in Canterbury. It’s got the bougie food hall / farmers market vibe with a heartwarming local feel.

There’s a restaurant menu of seasonal dishes (using ingredients from the local producers) or there are individual stalls selling everything from amazing bread and cakes to cheese and cocktails.

Where to stay in Canterbury

To truly step back in time, I’d recommend a night at House of Agnes – a historic travellers inn which dates back to the 13th century. It was even mentioned in the Charles Dickens’ story David Copperfield!

House of Agnes Canterbury
House of Agnes has a lot of history to it

This hotel has retained many of its original features, with wonky beams and old–fashioned windows. It’s nice and central too, perfect for a short break in Canterbury.

Day 2: Chilham

What to do in Chilham

So, you’ve got to know your way around Canterbury. Now, it’s time to swap city for country as you explore Chilham, a beautiful village just 8 minutes away by train from Canterbury West.

chilham church
Chilham Church

Chilham is a charming place, with a picturesque village green flanked by old timber-framed houses, a pretty church and a spectacular castle built back in 1616. I’d recommend venturing inside the castle before having a lovely wander around the landscaped gardens. Then, take in the charm of the village before refuelling at the village pub.

How pretty is Chilham?

After lunch, it’s time to follow in the footsteps of pilgrims as you follow the North Downs Way back to Canterbury. Alternatively, you could spend the evening in Chilham, enjoying a stay at The Woolpack Inn.

Where to eat and drink in Chilham

The White Horse in Chilham is one of those good old country pubs! The sort you dream about finding by chance, with roaring fires in winter and a great garden for balmy summer days. Serving authentic pub grub, it’s the ideal place to stop for lunch on your day trip from Canterbury.

the white horse chilham
The White Horse is a great place to stop for lunch in Chilham

Where to stay in Chilham

If you fancy staying in Chilham overnight, rather than returning to Canterbury, The Woolpack Inn offers comfortable accommodation right in the heart of the quintessential English village. There are 14 rooms in total, some with four poster beds, ideal for a romantic break.

Day 3: Whitstable

What to do in Whitstable

I love trips to the coast, and in my opinion, Whitstable is one of the best seaside day trips in the south of England. It’s easily accessible from London, so even if you want to dip in and out of this itinerary, it’s a great option for a day out.

If you’re continuing on your merry way from Chilham or Canterbury, you can hop on a train directly to the coast or, even better, hire a bike and cycle the Crab and Winkle Way – a 7 mile route that takes you from Canterbury to Whitstable.

crab and winkle way path
You could cycle the Crab and Winkle Way from Canterbury to Whitstable
whitstable cycling
There are some lovely places to cycle in Whitstable

Once in Whitstable it’s time to breathe in the salty sea air, enjoy some fresh seafood and check out the independent shopping scene. There’s everything here from tiny delis and hipster cafes to gift shops and clothing stores.

Sundae Sundae, Whitstable, Kent
Sundae Sundae is the best place for ice cream in Whitstable, Kent
Beach huts on Tankerton Slopes, walking from Whitstable towards Herne Bay
I love the colourful beach huts on Tankerton Slopes near Whitstable

A highlight is the walk along the promenade from Whitstable towards Herne Bay, which passes rows of colourful beach huts on Tankerton Slopes. If the weather is nice, you could stop for a swim or a paddle, before making your way back to the buzzy town.

Where to eat and drink in Whitstable

If you’re a foodie like me you’ll find yourself spoiled for choice in this seaside town. Whitstable is famed for its fresh fish and seafood, in particular oysters. On my last trip we picked up half a dozen for £10 from The Forge, and sat on the pebbles slurping them!

Oysters in Whitstable
You have to have a plate of oysters in Whitstable

Wheelers Oyster Bar is one of the most famous places to eat in town. As well as the fresh oysters, don’t miss the legendary crab tarts. For a mid-afternoon treat, pick up an ice cream at Sundae Sundae.

Wheelers Oyster Bar, Whitstable
Wheelers Oyster Bar is one of the most famous restaurants in Whitstable

Or for something more substantial, book a table at The Whitstable Oyster Company. The menu changes regularly to showcase the freshest catches. When I visited I had the pan-fried Thornback Ray wing with butter and capers – a local fish cooked with care and flavour.

Dinner at The Whitstable Oyster Company
Dinner at The Whitstable Oyster Company

Where to stay in Whitstable

If you’ve hired bikes in Canterbury, you can cycle back to the city along the Crab and Winkle Way. Alternatively, you could make a night of it and stay in Whitstable.

The most famous hotel in Whitstable is Hotel Continental. I’d describe it as a classic British seaside hotel. It has lovely views and is in a great location for exploring all that the town has to offer.

Alternatively, there are lots of amazing accommodation options available on AirBnb. I love the look of this 3-bed fisherman’s cottage, a stone’s throw from Whitstable Harbour. There’s also this house with sea views and an epic roof terrace. Both of these would be great for families following this Canterbury to Dover itinerary.

whitstable airbnb cottage
How about renting a cottage like this on Airbnb in Whitstable?

Day 4: Shepherdswell and Dover

What to do in Shepherdswell

For the final day of this epic route from Canterbury to Dover, we’re covering some seriously well-trodden ground. It’s time to walk or cycle the first miles of the Via Francigena – a pilgrimage route that leads from Canterbury all the way to… ROME! Can you believe it?! This ancient route is said to date back well over 1,000 years.

Where will it take you? Well, if you’re on foot, then I’d recommend aiming for the picturesque village of Shepherdswell. It’s a few hours walk from Canterbury, and the route passes through lush Kent countryside. Once there, you can wander through the pretty streets and enjoy a meal or a pint in a local pub.

Shepherdswell is also home to the East Kent Railway; a heritage railway preserved by volunteers. Time it right and you might be able to hop on a restored electric or diesel train and enjoy the five-mile round trip.

east kent railway
You could enjoy a little ride on the East Kent Railway

Alternatively, you could make the journey from Canterbury to Dover on two wheels. After visiting Shepherdswell, it’s under an hour by bike to Dover on the coast. Riding towards those rugged white cliffs will round off your Kent adventure in style!

white cliffs of dover
The white cliffs of Dover are an amazing sight

Wherever you end up, it’s easy to hop on a train back to your start point in Canterbury or all the way back to London.

Where to eat and drink in Shepherdswell

If you’re looking to sample beers from local independent breweries, don’t miss micropub The Tipsy Gardener in Shepherdswell. It’s located inside an 18th century converted barn, plus there’s a courtyard garden for those days when the sun is shining.

tipsy gardener micropub
Tipsy Gardener Micropub in Shepherdswell

Where to stay in Shepherdswell

In terms of accommodation, The Oast B&B is a lovely place to stay in Shephersdwell. It’s in an Area of Outstanding Natural Beauty and is in the perfect spot if you fancy continuing along the North Downs Way or the Via Francigena.

Alternatively, if you fancy a quirky stay to finish your trip, how about spending a night in Peverell’s Tower inside Dover Castle? Once a prison, it was added by Henry lll in the 13th century and is packed full of history. If you suffer from nightmares, it might not be the most relaxing place to rest, but you’ll definitely return home with a few stories!

dover castle
Did you know you can stay in Dover Castle?

Thanks to the National Trails for sponsoring this content.

I hope this guide has given you a dose of travel inspiration for your next English staycation. If you’re looking for more information, I’d recommend taking a look at the North Downs Way site.

Also, for more local guides, take a look at my Whitstable day trip and my guide to Rochester.

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long weekend in kent

With a passion for food, fun and adventure, Chloe is the content creator behind one of the UK's top travel blogs Wanderlust Chloe. From volcano boarding in Nicaragua, to sailing around Sicily and eating her way around Japan, her travels have taken her to some of the coolest spots on the planet. Named Travel Influencer of the Year in 2022, Chloe regularly works with a number of tourism boards, producing inspirational travel content across multiple platforms. Find out more about Chloe here.

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