Explore Helmsley’s Enchanting Landscapes on this Helmsley Circular Walk

This Helmsley circular walk begins in the picturesque North Yorkshire market town of Helmsley. Park in the Cleveland Way Car Park, situated just off the B1257 on the western side of town. Exit the car park, turn right, and follow Cleveland Way back to the B1257. Cross the road and take Canons Garth Lane, nestled between the Feversham Arms Hotel and the Church of All Saints. The road bends right, becoming Carlton Lane. Quickly take a left into Warwick Place.

Proceed along Warwick Place, passing the cemetery on your left. At the end of the road, continue straight ahead on the footpath. This path guides you between the cricket field on your left and a retirement village on your right. Follow the footpath signs across the fields into the enchanting woodlands of Ash Dale. Here, you’ll join the route of the Tabular Hills Walk. Head north along the forestry track through Ash Dale for about 1¾ miles (2.8 kilometres).

The time to leave the dale is marked by a bench and signpost. The route is signposted to Carlton. This is a key section of this Helmsley circular walk.

When the path splits, with one direction bending left and the other turning right, take the right-hand path, effectively making a U-turn. This trail is signposted to Carlton. Ascend out of the woods onto a track labelled Keld Lane on the Ordnance Survey map. Continue east along the stone track until you reach Carlton Road. Turn left and follow this tranquil road north.

After approximately half a mile (800 metres), the road dips slightly. Take the track on your left towards Carlton Grange. Head west past the farm, following the public footpath across farmland and through a forest to reach the minor road at High Baxton’s Farm. Turn left and walk south for about a quarter of a mile (400 metres). Then, turn right and follow the path beside the fields until you reach the woodlands of Acre Grain Plantation.

I need to walk along the road for about one-quarter of a mile (0.4 kilometres) from High Baxton’s Farm to the point where I turn right to continue my Helmsley circular walk.

A sign will direct you south along the woodland’s eastern edge for roughly one-third of a mile (0.5 kilometres). Descend to meet the main forestry track leading south through Collier Hag Wood. The trail continues through Beck Dale for over two miles (3.2 kilometres) and is easy to navigate. This stretch of the Helmsley circular walk is particularly serene, with the sounds of nature accompanying your hike. Eventually, you will come across a sawmill on your right.

Soon after passing the sawmill, the stone track leads uphill. Instead, take a right turn, crossing a footbridge and following the path along Borough Beck. This path will guide you to the main road, the B1257. Follow the road down to return to the Cleveland Way Car Park, where you started your Helmsley circular walk.

If time permits, take a leisurely stroll around Helmsley town centre. The town is delightful, offering an array of shops, cafes, restaurants, bars, and more, providing a perfect end to your Helmsley circular walk. This final recommendation ensures you fully enjoy the vibrant and welcoming atmosphere of Helmsley after your trek.

Helmsley Circular Walk: Maps and Tools

Visit either the OS Maps website or the Outdooractive website to view this walking route in greater detail. Both platforms offer a range of features, including the ability to print the route, download it to your device, and export the route as a GPX file. You can also watch a 3D fly-over and share the route on social media.

Helmsley Circular Walk: Distance, Duration, Statistics

Distance: 8¼ miles

Distance: 13½ kilometres

Duration: 3¾ hours

Ascent: 673 feet

Ascent: 205 metres

Type: Circular walk

Area: North York Moors

Map: OS Explorer OL26

Parking: Google Maps

This path by the side of the field leads to the woodlands of Ash Dale Plantation on the northern side of Helmsley town centre.

The best map to use on this walk is the Ordnance Survey map of the North York Moors Western Area, reference OS Explorer OL26, scale 1:25,000. It clearly displays footpaths, rights of way, open access land and vegetation on the ground, making it ideal for walking, running and hiking. The map can be purchased from Amazon in either a standard, paper version or a weatherproof, laminated version, as shown below.

About Helmsley

Overview of Helmsley’s History

Helmsley is a market town and civil parish in North Yorkshire, England. Historically part of the North Riding of Yorkshire, the town is situated where Ryedale leaves the moorland and joins the flat Vale of Pickering. Helmsley grew around its strategic position at a road junction and river crossing. The town retains its medieval layout around its market place, with more recent developments extending north and south of Bondgate. After completing your Helmsley circular walk, it is worth exploring the town, which is associated with the Earls of Feversham. Their ancestral home, Duncombe Park, overlooks Helmsley Castle.

Early Settlements and Archaeological Discoveries

Archaeological evidence suggests that Helmsley was first settled around 3000 BC. Small farming communities thrived here throughout the Neolithic, Bronze, and Iron Ages, continuing into Roman times. Finds of beehive querns confirm local agriculture and grain milling since at least the Iron Age. Additional discoveries include Roman pottery and a second-century coin. In 2011, the BBC Two programme ‘History Cold Case’ featured an investigation into 2000-year-old skeletons found in Windy Pits caves, concluding that one had been a ritual killing victim.

The ancient settlement, known in Old English as Elmeslac, pre-dates the Domesday Book and means ‘Helm’s forest clearing’. Viking influence is evident in the Old Norse ‘gate’ ending of many street names. Since the Norman Conquest, ownership of Helmsley’s land has changed hands only twice. Initially governed within the wapentake of Maneshou and held by William the Conqueror’s half-brother, the Count of Mortain, the land west of Helmsley was a royal deer park. The ancient pollarded oak trees in Duncombe Park date from this period and are now part of a national nature reserve. In about 1100, the estate passed to Walter Espec, founder of Rievaulx Abbey, and later to his heirs, the De Ros family. In 1191, Robert de Ros granted Helmsley its Borough Charter, establishing it as a market town.

Geographical Location and Layout

Helmsley is located on the River Rye along the A170 road, 14 miles (23 kilometres) east of Thirsk, 13 miles (21 kilometres) west of Pickering, and approximately 24 miles (39 kilometres) north of York. The southern boundary of the North York Moors National Park runs through Helmsley along the A170 road, placing the western part of the town within the National Park.

Helmsley retains its medieval layout around its market place, with narrow streets and burgage plots established with the granting of the Borough Charter in 1191. The market place remains central to Helmsley’s character, surrounded by buildings of considerable architectural interest. The town has been designated a conservation area to preserve its historical and architectural heritage.

Cultural and Economic Development

Market Town Status and Economic History

In 1191, Robert de Ros granted Helmsley its Borough Charter, formally recognising it as a centre of commerce and trade. This led to the development of long, narrow burgage plots for building purposes, still visible today on the west side of Castlegate and the east side of Bridge Street. This medieval layout highlights Helmsley’s historical importance as a commercial hub.

For centuries, Helmsley’s economy relied on large-scale sheep farming, wool production, and weaving. Despite challenges like marauding Scots and the Black Death, Helmsley grew steadily. The economy thrived on the wool trade until the dissolution of Rievaulx Abbey, after which the focus shifted to flax production, mainly located on Bond and Bridge Streets.

The Industrial Revolution in the 18th and 19th centuries brought significant changes, with the cottage weaving industry declining due to competition from industrial cities. Major developments included the rebuilding of the Church of All Saints, the construction of Helmsley Town Hall, and the arrival of the railway in 1871, which spurred further growth. With the decline of weaving, agriculture became the primary economic activity.

Modern-day Helmsley

Today, Helmsley is a vibrant tourist town, attracting visitors to its historical landmarks, such as Helmsley Castle and Duncombe Park. The town has won several accolades, including gold medals in the Large Village category of Yorkshire in Bloom for three consecutive years. These awards reflect the community’s efforts to maintain and enhance Helmsley’s appeal. The town square remains a popular meeting place, especially for motorcyclists who travel the B1257 road from Stokesley. Additionally, Helmsley is known for its picturesque walking routes, including the Helmsley circular walk I have described on this page.

Other Helmsley Circular Walks and Trails

Helmsley is the starting point of the Cleveland Way National Trail, which follows a horseshoe loop around the North York Moors National Park and the Yorkshire coast, extending approximately 110 miles (180 kilometres) to Filey. The trail offers walkers diverse landscapes, from heather moorlands to dramatic coastal cliffs.

The Cleveland Way is a major draw for walkers. It provides an excellent opportunity to explore the natural beauty of the North York Moors and the Yorkshire coast. The trail’s starting point in Helmsley enhances the town’s appeal as a destination for tourists seeking scenic walking routes. The trail complements other popular routes, such as the Helmsley circular walk featured on this page, and another Helmsley walk I have written about, both starting from the same location.

Helmsley Circular Walk: My Photos

The Church of All Saints in Helmsley, North Yorkshire, is an Anglican parish church with origins predating the Norman Conquest. The presence of a hogback gravestone in the porch and its mention in the Domesday Book of 1086 attest to its ancient roots. In the 19th century, the church underwent significant rebuilding funded by the Earl of Feversham. This renovation resulted in the loss of some original features but introduced fine stained glass by Hardman & Co. Since 1955, the church has been a Grade II listed building. Additionally, it houses a Harrison & Harrison pipe organ installed in 1931, incorporating elements from an earlier 1868 organ.

The Church of All Saints in Helmsley, North Yorkshire, is an Anglican parish church with origins predating the Norman Conquest.

This photo shows Helmsley’s Old Cemetery, with Helmsley’s New Cemetery located on the other side of the wall. Both cemeteries, owned by Helmsley Town Council, are adjacent but managed differently. They reflect their current use, with both open from dawn to dusk. The Old Cemetery benefits from volunteers who create conservation areas, build woodpiles, and clear litter, fallen branches, sticks, and detritus. This less intensive management enhances wildlife and biodiversity, attracting many visitors and photographers. In spring, snowdrops are in full bloom. Owls and voles are often seen, though voles can make the surface uneven in grassy areas. Conversely, the New Cemetery, the northernmost area without trees and featuring open grass, is actively used for burials and ashes plots.

This photo shows Helmsley's Old Cemetery, with Helmsley's New Cemetery located on the other side of the wall.

The view across the cricket field towards the pavilion of Helmsley Sports Club showcases a vibrant community hub. The club is home to Duncombe Park Football Club, Duncombe Park Cricket Club, Helmsley Tennis Club, and Helmsley Bowling Club.

The view across the cricket field towards the pavilion of Helmsley Sports Club showcases a vibrant community hub.

This path by the side of the field leads to the woodlands of Ash Dale Plantation on the northern side of Helmsley town centre. The path follows the route of the Tabular Hills Walk.

This path by the side of the field leads to the woodlands of Ash Dale Plantation on the northern side of Helmsley town centre.

The start of the walk north through Ash Dale follows a section of the Tabular Hills Walk. It is a pleasant and easy path to navigate through the lush woods of Ash Dale Plantation.

The start of the walk north through Ash Dale follows a section of the Tabular Hills Walk.

As I progress through Ash Dale, a group of tall, slender trees stands in a neat row along the trail. A small, simple wooden bench is nestled at the base of one of the trees, inviting me to sit and enjoy the peaceful surroundings and have a coffee from my flask.

As I progress through Ash Dale, a group of tall, slender trees stands in a neat row along the trail.

The tree-lined path cuts through Ash Dale, leading into the distance. The length of the path is about one and three-quarters of a mile (2.8 kilometres) from entering the dale to leaving it.

The tree-lined path cuts through Ash Dale, leading into the distance. The length of the path is about one and three-quarters of a mile (2.8 kilometres) from entering the dale to leaving it.

The time to leave the dale is marked by a bench and signpost. The route is signposted to Carlton. Again, this is still following the Tabular Hills Walk. The route heads out of the dale east on a track called Keld Lane.

The time to leave the dale is marked by a bench and signpost. The route is signposted to Carlton. Again, this is still following the Tabular Hills Walk.

A tall, majestic ash tree marks the way on the side of Keld Lane, bordered on both sides by a hedgerow. The tree signifies the point about one-third of the way round this Helmsley circular walk.

A tall, majestic ash tree marks the way on the side of Keld Lane, bordered on both sides by a hedgerow. The tree signifies the point about one-third of the way round this Helmsley circular walk.

The minor road north of Carlton is very quiet with hardly any traffic. I walk for about half a mile (0.8 kilometres) before heading down a dip in the road, then turn left to Carlton Grange. This is where I leave the Tabular Hills Walk.

The minor road north of Carlton is very quiet with hardly any traffic. I walk for about half a mile (0.8 kilometres) before heading down a dip in the road, then turn left to Carlton Grange.

This is the farm at Carlton Grange, which I pass as I walk west along the track to re-enter Ash Dale Plantation at the northern tip of Ash Dale.

This is the farm at Carlton Grange, which I pass as I walk west along the track to re-enter Ash Dale Plantation at the northern tip of Ash Dale.

The route from Carlton Grange back into Ash Dale follows the sides of the farmer’s fields. Public footpath signs mark the way. This is approximately the halfway point of this Helmsley circular walk.

The route from Carlton Grange back into Ash Dale follows the sides of the farmer’s fields. Public footpath signs mark the way. This is approximately the halfway point of this Helmsley circular walk.

I need to walk along the road for about one-quarter of a mile (0.4 kilometres) from High Baxton’s Farm to the point where I turn right and follow the public footpath to get to Acre Grain Plantation. As before, the road is quiet with minimal traffic. The road passes under a canopy of neatly aligned trees.

I need to walk along the road for about one-quarter of a mile (0.4 kilometres) from High Baxton’s Farm to the point where I turn right and follow the public footpath to get to Acre Grain Plantation.

Upon entering Acre Grain Plantation from High Baxton’s Farm, a makeshift wooden bench marks the spot. It’s no more than a log lying across the stumps of two cut-down trees. However, it’s welcome when you’ve been looking for a place to stop for a break and have a bit of lunch.

Upon entering Acre Grain Plantation from High Baxton’s Farm, a makeshift wooden bench marks a key turning point of my Helmsley circular walk.

Initially, the path south from the handy bench follows the eastern edge of the woods. It’s marked by a signpost, and it’s best to follow the path and not drop down into the valley too early.

Initially, the path south from the handy bench follows the eastern edge of the woods. It’s marked by a signpost, and it’s best to follow the path and not drop down into the valley too early.

The path along the eastern side of the woods is picturesque, easy to walk along, and peaceful, lined with tall pine trees. It is a highlight of this Helmsley circular walk and about two-thirds of the way round.

The path along the eastern side of the woods is picturesque, easy to walk along, and peaceful, lined with tall pine trees. It is a highlight of this Helmsley circular walk and about two-thirds of the way round.

After about one-third of a mile (0.5 kilometres) along the eastern edge of the woods, the path descends into the valley to join the main track, which leads south through Collier Hag Wood.

After about one-third of a mile (0.5 kilometres) along the eastern edge of the woods, the path descends into the valley to join the main track, which leads south through Collier Hag Wood.

The track south through Beck Dale is similar to Ash Dale, easy to follow, and it meanders through the woods generally following the course of Borough Beck back to Helmsley.

The track south through Beck Dale is similar to Ash Dale, easy to follow, and it meanders through the woods generally following the course of Borough Beck back to Helmsley.

Exiting Beck Dale, a charming narrow footpath runs along the side of Borough Beck.

Exiting Beck Dale, a charming narrow footpath runs along the side of Borough Beck, near the end of my Helmsley circular walk.

The footpath emerges from the woods onto the B1257 on the north-west side of the town centre. This marks the end of the Helmsley circular walk.

The footpath emerges from the woods onto the B1257 on the north-west side of the town centre. This marks the end of the Helmsley circular walk.

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