Outdoor Adventures

Five Crosses Midwinter Hike North York Moors Challenge Walk

With Mark Reid FRGS – author of ‘The Inn Way’ & Mountain Leader

Lilla Cross Five Crosses challenge walk north york moors

Winter Solstice ‘sunrise to sunset’ challenge walk 
33.5 km (21 miles) – 700 metres of ascent – 10 hours

The Five Crosses Midwinter Hike is a new challenge walk that links five ancient moorland crosses on the North York Moors, walking from sunrise to sunset on the shortest day of the year. This long distance challenge walk starts and finishes at Goathland, in the heart of the North York Moors.

See photos from our previous walks: Dec 2020


The Five Crosses Midwinter Hike is a 21 mile route with 700m of climbing that will take around 10 hours to complete. The route starts and finishes at Goathland, famed for its Heartbeat and Harry Potter connections, and takes in the rolling moorlands to the south and east, including Wheeldale Moor, Saltergate Moor, Fylingdales Moor and Goathland Moor, visiting the following historic crosses along the way:

1. Mauley Cross
2. Malo Cross
3. Lilla Cross
4. Ann’s Cross
5. York Cross


From Goathland, we head south-west to the Roman Road across Wheeldale, the best preserved in Britain, from where we follow the line of the Roman Road to reach the medieval Mauley Cross in the vast Cropton Forest. We then turn eastwards to reach the dramatic glacial meltwater channel of Newton Dale Gorge and then the famous Hole of Horcum, before we reach Malo Cross, an early 17th Century wayside cross. We then head northwards to reach one of England’s oldest crosses, the 7th Century Lilla Cross high on Fylingdales Moor. We then follow an ancient traders’ route across the moors passing two more crosses – Ann’s Cross and York Cross – before heading back into Goathland.

It is a demanding walk that requires a good level of fitness and so must be approached with preparation and training, but it is also a rewarding walk that will be remembered for many years as we walk from dawn to dusk on the shortest day of the year, visiting prehistoric burial mounds, standing stones and defensive ditches, Roman Roads and medieval moorland crosses.

Much of this walk follows clear paths and tracks across open moorland, with some sections through forest and valleys. The paths will be rough and muddy in places, and the only significant climb of the day is the descent into and ascent out of Newton Dale Gorge. This walk will start and finish in the dark – headtorches essential!

Malo Cross North York Moors Five Crosses Challenge Walk

Mark Reid knows the North York Moors like the back of his hand and will guide you around this route (whilst also sharing his knowledge of the area), so that you can forget about navigating and concentrate on enjoying the walk!

This guided walk is designed for solo or small groups of walkers who want to take on the Five Crosses Midwinter Hike, but don’t want to worry about route finding.

  • Fully guided walk with Mark Reid (Mountain Leader)
  • Experience the comaraderie of walking a challenge route with other like-minded walkers
  • Discover the history, heritage & geography of the North York Moors
  • Share your sense of achievement with your fellow walkers
  • Small group sizes – 8 people per Mountain Leader
  • You are GUARANTEED not to get lost on our guided walk!
north york moors challenge walk five crosses

7am: Meet at Goathland. Weather forecast, gear check & briefing.
7am – 5pm: Fully guided walk around the Five Crosses Midwinter Hike challenge walk
5pm: Debrief back at Goathland, then head home

NB: Sunrise is 08:22 and sunset is 15:40. We will be walking in the dark for approximately 1 hour in the morning and 2 hours in the afternoon. Finish time is approximate




This includes:

  • Full details of what to wear, bring and expect along the walk
  • Fully guided walk around the Five Crosses Midwinter Hike challenge walk, with Mark Reid (Mountain Leader)
  • Completers' Certificate
  • Use of our outdoor gear if required.
  • TeamWalking Loyalty Reward scheme
NB: Please provide a packed lunch, lots of snack food and plenty of water for this walk, as well as a good pair of walking boots. we will be walking from dawn to dusk, with the first and last hour or two of the walk in the dark.Please see the Walk Overview for full details of what to wear, bring and general advice.