Helmsley Circular Walk

Helmsley Circular Walk

Helmsley Circular Walk – An Easy 4-Mile Walk in North Yorkshire

Looking for an easy circular walk around Helmsley? This approximately 4-mile Helmsley Circular Walk explores one of North Yorkshire's most attractive market towns, combining countryside, riverside scenery and centuries of local history.

Lyn and I personally walked and photographed this route for The White Shire.

We found it to be a nice, easy and enjoyable walk, ideal if you want to combine a relatively short walk with plenty of time to explore Helmsley itself.

A quick note about the distance: this walk is approximately 4 miles. I accidentally forgot to stop our GPS tracking app when we finished and left it running when we drove away, so rather than pretend I've got a precise figure, I'm sticking with approximately four miles.

These things happen!

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Helmsley Circular Walk at a Glance

Distance: Approximately 4 miles

Route type: Circular

Difficulty: Easy

Location: Helmsley, North Yorkshire

Area: North York Moors

Nearby: Rievaulx, Kirkbymoorside, Pickering and Thirsk

Terrain: Town paths, countryside paths, riverside sections and tracks

Highlights: Helmsley, Helmsley Castle, River Rye, North Yorkshire countryside, historic Market Place and views around Duncombe Park

Walked and photographed by: Michael and Lyn Palmer, The White Shire

About Our Helmsley Circular Walk

Lyn and I found this to be a nice, easy walk.

At approximately four miles, it's also a good distance if you want a relatively gentle walk without spending the entire day on the trail.

But Helmsley gives you something extra.

This isn't somewhere we'd recommend arriving, completing the walk and immediately driving home.

The town itself is worth exploring.

You've got Helmsley Castle, the Market Place, independent shops, cafés, pubs, historic streets and Helmsley Walled Garden all within a relatively compact area.

For us, that makes this a particularly good Yorkshire walk for turning into a full day out.

Why is the Distance Approximate?

Normally, Lyn and I GPS record our White Shire walks so we can give you an accurate distance.

This one didn't quite go to plan.

We completed the walk, got back to the car and drove away.

Unfortunately, I forgot to switch the walking app off.

So according to the GPS, our walk suddenly became considerably faster!

Rather than publishing a made-up precise figure, we're calling this one approximately four miles.

It also serves as a useful reminder that the walks on The White Shire aren't generated from somebody else's route.

We're actually out there walking them.

Sometimes that means getting muddy.

Sometimes it means taking a wrong turn.

And occasionally it means forgetting to turn the app off.

Helmsley: A Brief History

Helmsley sits on the southern edge of the North York Moors National Park.

Its position has been important for centuries.

The River Rye runs to the south of the town, while Borough Beck flows through Helmsley before joining the river.

The river crossing, surrounding roads and availability of water all helped shape the settlement.

There is evidence of activity in the area stretching back before the medieval period, but the Helmsley we recognise today developed principally as a medieval market town.

Its castle, church, market and surrounding estates all played important roles in that story.

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Medieval Helmsley

By the medieval period, Helmsley was developing into an important local settlement.

Its location gave it several advantages.

Roads converged here.

The River Rye could be crossed.

Agricultural communities surrounded the town.

And eventually an imposing castle controlled the landscape from higher ground to the west.

Helmsley's medieval street pattern still influences the town today.

When Lyn and I walk through places like this, that's one of the things we enjoy looking for.

Modern shops and cafés might occupy the buildings, but the streets themselves can be centuries old.

Helmsley Market Place

The Market Place remains the heart of Helmsley.

For centuries, markets were enormously important to Yorkshire towns.

Farmers, traders and craftspeople needed somewhere to sell their goods, while local people needed somewhere to buy them.

Market towns such as Helmsley therefore became important economic and social centres for the surrounding countryside.

The wide Market Place still reflects that history.

Today the businesses may be different, but Helmsley continues to attract visitors from across Yorkshire and much further afield.

Helmsley Castle

Helmsley Castle is one of the town's most important landmarks.

The castle has around 900 years of history.

Over those centuries, it changed enormously.

What began as a medieval stronghold developed into a much more comfortable Tudor residence.

Later, during the English Civil War, the castle once again became strategically important.

Today its ruins provide a fascinating reminder of those different periods.

For Lyn and me, being able to combine a countryside walk with somewhere as interesting as Helmsley Castle is a major advantage.

From Medieval Fortress to Tudor Mansion

Castles didn't remain unchanged.

As warfare, wealth and expectations of comfort developed, many medieval fortresses were altered.

Helmsley was no exception.

Parts of the castle became considerably more residential.

Owners wanted somewhere impressive to live as well as somewhere defensible.

That mixture of military architecture and later domestic additions is one of the reasons Helmsley Castle is so interesting.

You're not simply looking at one period of history.

You're looking at centuries of change within the same site.

Helmsley Castle and the Civil War

The English Civil War brought another dramatic chapter.

Helmsley Castle became a Royalist stronghold.

After a lengthy siege, Parliamentary forces eventually captured it.

Much of the castle was subsequently deliberately damaged so it couldn't easily be used as a defensive position again.

Some residential buildings survived.

The resulting mixture of ruins and surviving structures is largely what visitors explore today.

All Saints Church

All Saints Church stands close to the historic centre of Helmsley.

A church existed here by the medieval period, and the site has an even longer religious history.

Although the building underwent substantial restoration during the Victorian era, earlier features survive.

These include Norman architectural elements.

There's also a remarkable Norse hogback stone in the church porch.

It's another reminder that Helmsley's story stretches back well beyond the attractive market town we see today.

What is a Hogback Stone?

Hogback stones are distinctive carved stone monuments associated with the Viking Age.

They generally date from around the 10th and early 11th centuries.

Their curved shape has sometimes been compared to the roof of a house.

Examples have been discovered across northern England, particularly in areas influenced by Scandinavian settlement.

Finding one at Helmsley adds another fascinating layer to the town's history.

Yorkshire's Viking past isn't only found in York.

Evidence survives throughout the wider region.

The River Rye

The River Rye forms an important part of the landscape around Helmsley.

It flows through this part of North Yorkshire before eventually joining the River Derwent.

For centuries, rivers influenced where communities developed.

They provided water, powered mills, created transport obstacles and shaped the surrounding farmland.

Today, the river adds another dimension to walking around Helmsley.

The combination of water, countryside and the historic town gives this relatively short route plenty of variety.

Borough Beck

Borough Beck flows through Helmsley before joining the River Rye.

Small waterways such as this are easy to overlook.

Historically, however, they could be extremely important.

Water availability influenced settlement, farming and industry.

The beck also contributes to the character of the historic town today.

For us, noticing these smaller landscape features is part of exploring somewhere properly rather than simply concentrating on reaching the end of a walk.

Duncombe Park

Immediately west of Helmsley lies Duncombe Park.

The estate has played an important role in the development and appearance of the surrounding landscape.

The present mansion dates from the early 18th century and stands within extensive parkland.

The Duncombe family became closely associated with Helmsley and the wider area.

The estate also helps explain why the countryside immediately surrounding the town has retained so much of its historic character.

Helmsley Walled Garden

Close to Helmsley Castle you'll find Helmsley Walled Garden.

The garden dates back to 1758 and was originally created to grow fruit and vegetables for the Feversham family at Duncombe Park.

Like many traditional kitchen gardens, its original purpose declined during the 20th century.

Eventually, the site became neglected.

Its modern story began in the 1990s when Alison Ticehurst recognised its potential.

The garden was gradually restored with a strong emphasis on horticulture, community and wellbeing.

Today, it's another reason to allow extra time when visiting Helmsley.

A Garden Designed to Catch the Sun

One particularly interesting feature of Helmsley Walled Garden is its unusual shape.

Rather than forming a simple rectangle, the garden was laid out as a parallelogram.

The idea was practical.

The angled design helped maximise the amount of sunlight reaching the walls and reduce shadow.

That created warmer growing conditions in a northern climate.

It's a lovely example of how historic garden design often combined appearance with very practical horticultural thinking.

The Cleveland Way

Helmsley is particularly famous amongst walkers because the Cleveland Way begins here.

The long-distance National Trail crosses some of North Yorkshire's most dramatic landscapes before eventually reaching the coast.

It takes walkers through the North York Moors and towards places such as Osmotherley, Saltburn, Whitby and Scarborough before finishing at Filey.

Our approximately four-mile Helmsley route is obviously a very different proposition.

You won't need several days or a huge rucksack for this one.

But knowing you're walking around the starting point of one of Yorkshire's great long-distance trails gives Helmsley an extra connection with the walking world.

Helmsley and the North York Moors

Helmsley sits at the southern edge of the North York Moors National Park.

That makes it an excellent gateway to the wider area.

Head north and the landscape becomes increasingly dominated by hills, valleys, woodland and eventually open moorland.

Head south and the character changes towards the Vale of Pickering and Howardian Hills.

Helmsley sits between these different landscapes.

That's one of the reasons it's such a good base for walking.

Walking Around Helmsley

Our route gives you an opportunity to see more than just the town centre.

Leaving the busier streets behind, you quickly begin to appreciate the surrounding North Yorkshire countryside.

For Lyn and me, that's what makes a circular route around somewhere like Helmsley enjoyable.

You get both sides of the place.

There's the historic market town with its shops, castle and cafés.

Then there's the quieter countryside surrounding it.

Is the Helmsley Circular Walk Difficult?

No.

Lyn and I found our Helmsley Circular Walk to be an easy walk.

It's approximately four miles, so it's also a manageable distance if you're looking for something relatively short.

We didn't find anything particularly demanding about the route.

As always, conditions can change depending on the weather.

Countryside paths may become muddy after prolonged rain, so we'd still recommend sensible walking footwear.

Overall, we'd definitely class this amongst our easier White Shire walks.

How Long is the Helmsley Circular Walk?

Approximately four miles.

As I've already confessed, I can't give you our usual precise GPS measurement because I forgot to switch the tracking app off before driving away.

We'd rather tell you that than pretend otherwise.

How long you'll need depends on your walking pace.

But we'd allow considerably more time than simply the time required to walk four miles.

Helmsley is worth exploring.

Is Helmsley Good for Walking?

Definitely.

You have everything from relatively short local walks to major long-distance routes.

The surrounding North York Moors provide almost unlimited walking possibilities.

And Helmsley itself gives you an excellent place to start and finish.

You can walk, explore the town and then find somewhere for something to eat or drink afterwards.

That's our sort of day out.

Is Helmsley Worth Visiting?

Yes.

Even if you weren't coming for our walk, we'd recommend exploring Helmsley.

The historic Market Place, castle, church, independent businesses and surrounding countryside give the town plenty of character.

Helmsley Walled Garden adds another attraction nearby.

And the North York Moors are right on the doorstep.

That combination makes Helmsley one of those Yorkshire places where you can easily spend much longer than you originally planned.

Can You Visit Helmsley Castle?

Yes.

Helmsley Castle is a visitor attraction managed by English Heritage.

You can explore the remains and discover the castle's development from medieval fortress to Tudor residence and Civil War stronghold.

Opening times and admission arrangements can change, so we'd recommend checking the current visitor information before making a special journey specifically to enter the castle.

Even if you're simply completing our walk, the castle remains one of Helmsley's defining landmarks.

Is Helmsley Walled Garden Worth Visiting?

We think it's well worth considering.

It's particularly convenient because the garden sits close to Helmsley Castle.

The combination of historic walls, planting and views towards the surrounding landscape gives it plenty of character.

Its restoration story and emphasis on therapeutic horticulture make it more than simply an ornamental garden.

If you enjoy gardens, we'd definitely leave some extra time for it.

What Else Can You Visit Near Helmsley?

Rievaulx Abbey is one of the obvious choices.

The spectacular ruined Cistercian abbey lies only a few miles from Helmsley and is one of North Yorkshire's great historic sites.

The North York Moors provide countless other possibilities.

You could also explore nearby villages and market towns or simply spend more time discovering Helmsley itself.

See what's on in North Yorkshire for events, shows, festivals and other ideas for a day out.

When is the Best Time to Walk Around Helmsley?

We'd consider this walk throughout much of the year.

Spring and summer bring greener countryside and longer daylight hours.

Autumn can be particularly attractive as the surrounding trees change colour.

Winter gives Helmsley and the North York Moors another atmosphere entirely.

As always, we'd check the weather before setting off and choose footwear appropriate for the conditions.

Explore More of North Yorkshire

If you've enjoyed discovering Helmsley, there are plenty more places to explore with us around North Yorkshire.

Discover more North Yorkshire walks and find another route personally walked, photographed and GPS recorded by Michael and Lyn.

Or explore our complete collection of Yorkshire walks, covering routes across North, West, South and East Yorkshire.

Looking for somewhere else to explore? Discover North Yorkshire attractions and interesting places to visit.

You can also see what's on in North Yorkshire for events, shows, festivals and ideas for another day out.

About Michael and Lyn

Michael and Lyn Palmer explore Yorkshire together on foot, personally walking and photographing the routes featured on The White Shire.

Where possible, we GPS record our walks too.

Usually successfully.

Our walking guides combine first-hand experience with practical route information, local history and the character of the towns, villages and countryside we discover along the way.

We're not professional hikers – we simply enjoy getting out together, finding somewhere interesting to walk and discovering more of Yorkshire as we go.

Helmsley is a great example – a nice, easy walk combined with one of North Yorkshire's most interesting market towns.

Helmsley Circular Walk

View our Helmsley Circular Walk below and use it to help plan your own walk around the town and surrounding North Yorkshire countryside.

The route is approximately four miles and, based on our own experience, we'd rate it as easy.

Don't rush away afterwards.

Have a wander around Helmsley, explore the Market Place and, if you've got time, take a look at the castle or Walled Garden.

And one final piece of advice.

Remember to turn your walking app off before you drive home.

Apparently, that's quite important.

Helmsley Circular Walk

I think the walk is about 4 miles...I forgot to turn the app off and left it on when driving!!!

Helmsley Circular Walk