Itinerary
- Day 1
Helmsley
You'll make your own way to Helmsley and get settled into this old market town. Once you're there, you can wander around the keep ruins which hold a lot of history from the English Civil War. After that, the local pubs, cafes and shops are worth checking out if you want to get a feel for the place.
Optional Activities
- Visit the ruins of the keep
- Browse local pubs, cafes and stores
Landmarks Helmsley Keep 
- Day 2
Helmsley to Boltby or Kilburn
After breakfast, you'll walk through the wooded Rye Valley and head gently up toward the Tabular Hills. By late morning, you should reach Sutton Bank where the views are really nice, including a Victorian chalk horse carved into the landscape. The 12th century Rievaulx Abbey is along the route, so you can stop there. Later you'll stay in either Boltby or Kilburn, or head back to Helmsley if you prefer (there's an extra charge for that).
- Meals
- Breakfast
Included Activities
- Walk through Rye Valley to Sutton Bank viewpoint
- Visit Rievaulx Abbey (12th century)
Optional Activities
- Return to Helmsley for the night (additional cost)
Landmarks Sutton Bank Rievaulx Abbey Kilburn White Horse - Day 3
Boltby or Kilburn to Osmotherley
This day takes you along the escarpment of the Hambleton Hills with views across the York Valley. You'll follow the old Hambleton Cattle Drovers Road and eventually reach Osmotherley, a historic market and mining village. There's a converted 15th century church there and some interesting 12th century Scandinavian carvings to see if you want to explore a bit more.
- Meals
- Breakfast
Included Activities
- Walk along Hambleton Hills escarpment
- Follow Hambleton Cattle Drovers Road to Osmotherley
Landmarks Osmotherley - Day 4
Osmotherley to Great Broughton
This is the toughest day on the route. You'll be climbing up and down over a series of moors heading toward Clay Bank Top where you get good views when the weather cooperates. The walk takes you alongside the crags of Cringle Moor and the well-known Wainstones. Once you reach Clay Bank Top later in the day, you'll get a transfer to your accommodation in Great Broughton.
- Meals
- Breakfast
Included Activities
- Climb over moors to Clay Bank Top
- Walk alongside Cringle Moor and Wainstones crags
Landmarks Clay Bank Top Cringle Moor Wainstones - Day 5
Great Broughton to Kildale
Your hosts will drop you back at Clay Bank parking lot to start. From there it's a steep climb up to Urra Moor and Round Hill (454m), the highest point of the whole trip. You'll cross exposed moorland following an old Ironstone railroad line and drovers' roads, passing ancient boundary stones, burial mounds and cock pits. The walk takes you through the remote hamlet of Kildale with its old railroad station, then you climb up again to pass the Captain Cook memorial.
- Meals
- Breakfast
Included Activities
- Climb to Urra Moor and Round Hill (highest point at 454m)
- Walk along disused Ironstone railroad line
- Pass Captain Cook memorial
Landmarks Round Hill Kildale Captain Cook Memorial - Day 6
Saltburn-by-the-Sea
You'll continue through forests with a steep climb up to Rosberry Topping, which offers some really nice views when the weather cooperates. After that, the trail takes you through moorlands and Guisborough forests before dropping steeply down to Slapewath's old mineral mining areas. There's an optional stop in town if you want to grab something to eat or drink, then you'll hike the final 7 km to Saltburn-by-the-Sea, a Victorian seaside town with an interesting smuggling past. From here things shift and you'll start doing more coastal hiking instead of inland routes.
- Meals
- Breakfast
Included Activities
- Hike through forests with detour to Rosberry Topping
- Trek through moorlands and Guisborough forests
- Hike down to Slapewath ancient mineral mining area
- Coastal hike from Saltburn-by-the-Sea
Optional Activities
- Pub stop in Slapewath area
Landmarks Rosberry Topping Guisborough Forest Slapewath Saltburn-by-the-Sea - Day 7
Kildale to Whitby
You'll walk along dramatic cliffs with Rock Cliff near Boulby being the highest point on the English east coast. From there it's on to Staithes, a pretty fishing village where traditional cobles still work and where Captain Cook did his apprenticeship. Continue walking to Runswick Bay, a nice red-roofed village sitting against Jurassic slate cliffs that are great for fossil hunting. You'll stay 2 nights in Whitby, and you'll need to arrange your own transport from Runswick Bay to Whitby (bus or cab).
- Meals
- Breakfast
Included Activities
- Walk along coastal cliffs to Rock Cliff viewpoint
- Visit Staithes fishing village
- Visit Runswick Bay
Optional Activities
- Travel to Whitby by bus (at own expense)
- Arrange return cab transfer to Whitby (at own expense)
Landmarks Boulby Cliff Staithes Runswick Bay - Day 8
Whitby
This is a shorter walking day, so you have time to explore Whitby properly. You'll walk along cliffs from Runswick, pass through Sandsend, then walk above the beach into Whitby. This red-roofed town got wealthy from fishing, whaling, mining and shipbuilding between 1750 and 1850. The abbey ruins are worth visiting and there's a lot of Dracula history to find around town. The fish and chips here are supposed to be really good.
- Meals
- Breakfast
Included Activities
- Walk along coastal cliffs to Sandsend
- Walk into Whitby town
Optional Activities
- Visit Whitby Abbey ruins
- Follow Dracula Trail in town
- Enjoy fish and chips meal
Landmarks Whitby Abbey Whitby - Day 9
Whitby to Robin Hood Bay
The shortest walking day means you can have a leisurely breakfast and start later. Climb out of Whitby Bay using 199 steps to reach the old abbey ruins and St. Mary's church, which has an unusual boat deck construction inside. Follow the coastal cliffs which can have good birdlife depending on the season. Later you'll rejoin the Coast-to-Coast Trail for the final stretch into Robin Hood Bay, a small village that drops steeply down to the sea. The Bay Hotel has a terrace overlooking the sea which is perfect for relaxing with a drink.
- Meals
- Breakfast
Included Activities
- Climb 199 steps to abbey ruins and St. Mary's church
- Walk coastal cliffs to Robin Hood Bay
- Complete the Coast-to-Coast Trail
Optional Activities
- Visit Bay Hotel terrace
Landmarks Whitby Abbey St. Mary's Church Robin Hood Bay 
- Day 10
Robin Hood Bay to Scarborough
This is a longer walk taking you to Scarborough, the biggest settlement on the route. You'll pass through the abandoned resort of Ravenscar where you can still see Victorian street layouts. At nearly 200 meters above sea level, you get what might be the most beautiful view of the Yorkshire coast. The walk follows cliffs that gradually descend into Scarborough with its two sandy coves, castle ruins on a headland, and chances to swim or get ice cream. Scarborough has been a popular English seaside resort since the 1600s when people came for the spring water.
- Meals
- Breakfast
Included Activities
- Walk through Ravenscar abandoned resort
- Walk along coastal cliffs to Scarborough
Optional Activities
- Swimming
- Visit Scarborough castle ruins
- Enjoy ice cream and seaside activities
Landmarks Ravenscar Scarborough Castle 
- Day 11
Scarborough to Filey
The final section winds behind Cayton Sands and continues along the cliffs to Filey Brigg, a chalky shingle headland and nature reserve. When the tide is low you can cross the sands to finish at Filey, but if the tide is high you'll retrace your steps to reach this pleasant fishing and recreation spot.
- Meals
- Breakfast
Included Activities
- Walk along Cayton Sands
- Walk along cliffs to Filey Brigg
- Complete walk at Filey
Optional Activities
- Cross sands at low tide to Filey Brigg
Landmarks Filey Brigg Filey 
- Day 12
Filey
You'll depart from Filey after breakfast.
- Meals
- Breakfast
