Why Helmsley Is Having a Moment – And How to Visit from York
Why Helmsley Is Having a Moment – And How to Visit from York
Helmsley has been getting some rather high-profile attention.
Condé Nast Traveller recently asked whether this small North Yorkshire market town could be “North Yorkshire’s answer to the Cotswolds?”
It is a comparison that will probably make a few Yorkshire people smile.
Helmsley does not really need to be Yorkshire’s answer to anywhere.
It is very good at being Helmsley.
But the article does put its finger on something we have known for a long time: this relatively small town packs an extraordinary amount into one corner of North Yorkshire.
There is a ruined medieval castle.
A walled garden.
Independent shops.
Excellent places to eat.
Beautiful countryside immediately outside the town.
And, perhaps most importantly for us, Helmsley sits among some of the best places we visit on our private tours from York.
Condé Nast Traveller has helped put the spotlight on the town.
So we thought we would give you the Highwayman view.
Where is Helmsley?
Helmsley sits around 25 miles north of York, close to the edge of the North York Moors National Park.
It is one of those places that feels considerably further away from a city than the mileage suggests.
Leave York behind and the landscape quickly changes.
The roads become more rural, the villages smaller and the views wider.
By the time you arrive in Helmsley, you are firmly in North Yorkshire countryside.
That location is one of the reasons we like using the town on our tours.
Helmsley is not an isolated attraction.
It sits in the middle of an exceptionally rich part of Yorkshire.
Castle Howard lies in one direction.
Rievaulx Abbey is just outside the town in another.
Byland Abbey lies further south.
The North York Moors begin virtually on Helmsley’s doorstep.
That makes it a very useful piece of a much bigger Yorkshire day.
Is Helmsley really like the Cotswolds?
We can see why the comparison gets made.
Helmsley has attractive stone buildings, independent businesses, good food and the sort of traditional English market-town atmosphere that international visitors often come looking for.
But we would not travel to Helmsley expecting a miniature version of somewhere else.
North Yorkshire has its own character.
The buildings are different.
The landscape is different.
And within a few miles of the town you move from historic estates and ruined abbeys into the much rougher landscape of the North York Moors.
That contrast is one of the things that makes this part of Yorkshire so good to explore.
Helmsley is polished enough to make a lovely place to stop, but it still feels connected to the farming communities, villages and landscapes around it.
What is there to see in Helmsley?
Helmsley works extremely well as a place to wander rather than somewhere that requires a rigid itinerary.
The town centre is compact.
There are independent shops, cafés and places to eat surrounding the market square and nearby streets.
Helmsley Castle sits within easy walking distance of the centre.
The ruins have watched over the town for centuries and give Helmsley something that very few picturesque market towns can match.
Right beside the castle is Helmsley Walled Garden.
So you can move from the town centre to a medieval castle and then into a historic garden without needing to get back into the vehicle.
For us, though, one of Helmsley’s biggest strengths is what lies beyond it.
Rievaulx Abbey is just down the road
Drive out of Helmsley and it does not take long before you reach one of the most spectacular historic sites in Yorkshire.
Rievaulx Abbey sits in a secluded valley a few miles from the town.
The scale of the ruins can be surprising if you have never visited before.
This was once one of England’s great Cistercian monasteries.
Today its enormous stone remains rise out of a peaceful Yorkshire valley.
Helmsley and Rievaulx work beautifully together because they offer two completely different experiences within a very small area.
One is a lively market town.
The other is a vast medieval ruin surrounded by countryside.
It is exactly the sort of contrast we try to build into our tours.
And then there is Castle Howard
Castle Howard is another reason Helmsley makes sense as part of a day from York.
The great house and estate are among the best-known visitor attractions in Yorkshire.
If you are staying in York, combining Castle Howard with Helmsley immediately gives you more than simply a visit to one stately home.
You begin to explore the surrounding countryside as well.
That is how we approach our Castle Howard, Abbeys & North Yorkshire tour.
Rather than driving you to Castle Howard and straight back to York, we use it as part of a journey through this area.
Castle Howard.
Helmsley.
Rievaulx Abbey.
Byland Abbey.
Four places with completely different stories, joined together geographically into one private day.
Byland Abbey: another Yorkshire ruin worth knowing about
Rievaulx may be the more famous of the two abbeys, but we have a real soft spot for Byland.
Byland Abbey sits south of Helmsley and is another remarkable reminder of the wealth and power of medieval monastic Yorkshire.
It feels different from Rievaulx.
The setting is more open and the huge surviving rose window is one of its most distinctive features.
Visiting both abbeys also helps tell a much bigger story.
These places were not isolated ruins.
They formed part of a medieval landscape that stretched across this part of Yorkshire long before tourists arrived to photograph it.
For anyone interested in history, architecture or simply beautiful places, combining them in one route works extremely well.
Helmsley from York without a car
This is where the Condé Nast Traveller attention becomes particularly interesting for visitors staying in York.
Helmsley does not have a railway station.
You can reach the area using public transport, but the bigger challenge is not simply getting to Helmsley.
It is what happens next.
If you also want to visit somewhere such as Castle Howard, Rievaulx Abbey or Byland Abbey, you suddenly have several rural locations to connect.
That is much easier with road transport.
Of course, you can hire a car.
But plenty of our guests do not want to.
Some are visiting from overseas and do not fancy driving unfamiliar British roads.
Others simply do not want to spend a day of their holiday thinking about navigation, parking and directions.
That is precisely where a private driven tour from York comes in.
We collect you in York.
You get to enjoy the countryside.
We deal with the road.
Why we include Helmsley on our North Yorkshire tour
Some places on an itinerary are there because they are major attractions.
Others make the whole day work.
Helmsley does both.
It gives you time in a proper Yorkshire market town between some much larger historic sites.
After the grandeur of Castle Howard, Helmsley feels intimate.
After Helmsley, Rievaulx feels remote and dramatic.
Then Byland changes the atmosphere again.
This is important to us.
We do not want our tours to feel like somebody has searched “top ten Yorkshire attractions” and tried to squeeze as many as possible into one vehicle.
A good route should have a rhythm.
Big attraction.
Town.
Countryside.
Ruins.
Views.
And enough time to actually notice where you are.
Helmsley fits beautifully into that sort of day.
A gateway to the North York Moors
Helmsley is also one of the gateways to the North York Moors.
The national park begins around the town, and the famous Cleveland Way starts here before making its long journey through the moors and towards the Yorkshire coast.
That means you are right on the boundary between two different North Yorkshire landscapes.
Head one way and you find Castle Howard and the Howardian Hills.
Head another and you are moving into the North York Moors.
Continue far enough and eventually you reach places including Goathland, Whitby and the Yorkshire coast.
That geography is one reason Helmsley appears in so many conversations about exploring North Yorkshire.
It is right in the middle of it.
So, is Helmsley worth visiting from York?
Absolutely.
But we think Helmsley is at its best when you do not treat it as an isolated destination.
If you have a car, make a day of the surrounding area.
If you are staying in York without a car, a private tour makes it possible to join several of these places together without worrying about transport between them.
And if you are already planning to visit Castle Howard, we think adding Helmsley and the nearby abbeys creates a much richer picture of North Yorkshire.
Yorkshire does not need to be the Cotswolds
We understand the comparison.
And Condé Nast Traveller shining a light on Helmsley is thoroughly deserved.
But we would make one small Yorkshire amendment.
Come because it is Helmsley.
Come for the market town, the castle and the countryside.
Then go a little further.
See Rievaulx Abbey sitting in its valley.
Walk beneath the ruins of Byland.
Explore Castle Howard.
Look out across the North Yorkshire landscape between them.
That is when Helmsley starts to make sense.
Not as Yorkshire’s version of somewhere else.
But as a brilliant little town right in the middle of one of the best parts of Yorkshire to explore.
Highwayman Tours visits Helmsley as part of our private Castle Howard, Abbeys & North Yorkshire tour from York.
Your group remains private, with York pick-up and return and a local driver-guide throughout the day.
Explore the tour to see the full route and current availability.