Whitby
Walking Events Calendar near Whitby 2026-2027
Monthly updates for Whitby
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Whitby for 2026-2027! We've gathered 22 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
August 2026
Guided and supported crossing of the North York Moors between Ravenscar and Osmotherley, across open moorland to the coast. The route is just under 39 miles and groups are supported with checkpoints, water, snacks and blister plasters, with a max..
Guided and supported crossing of the North Yorks Moors from Osmotherley to Ravenscar, route is just under 39 miles. Groups get minibus transfer, water, snacks and blister plasters; walkers typically take 15 to 18 hours.
December 2026
Walkers can follow festive off road trails at Normanby Hall Country Park & Gardens on 5k or 10k routes with muddy spots and deer; a family 3k is untimed with wave starts.
January 2027
Circular 17.5 miles route starting and finishing at Robin Hoods Bay via Ravenscar and Hayburn Wyke, with food and water checkpoints and an 8 hour limit.
April 2027
The event offers a 10km walk on the Official Samaritans Way starting at Guisborough Rugby Club, Belmangate, Guisborough TS14 7BB. The trail can be muddy and is fully marshalled with stocked checkpoints, medical cover and food and drink at the fin..
Out and back trail of 10 km (7.4 miles) from Skinningrove along Cleveland Way cliffs with 890 ft climb, Saltburn checkpoint with water and snacks; walkers aged 15+ welcome.
The route is a walkable 14.35 miles from Redcar to Staithes along coastal cliffs and sand, with mud and rocks, two marshalled aid stations and a 5 hour cut off.
Walkers can follow the 26.57 mile coastal trail from Redcar to Whitby across cliffs, sand and mud, with four aid stations, marshaled checkpoints and a 10 hour cut off.
Guided and supported crossing from Osmotherley to Ravenscar across North York Moors covering just under 39 miles. Two guides, checkpoints and support provide water, sugar snacks and blister plasters; groups max 14, typical 15 to 18 hours.
May 2027
Guided and supported W to E crossing from Osmotherley to Ravenscar across North Yorks Moors moorland, covering just under 39 miles. Groups cap 14 walkers with two guides, minibus transfer to the far end and checkpoints with water, unlimited sugar..
Guided E W crossing from Ravenscar on the North Sea coast to Osmotherley across the North Yorks Moors, covering just under 39 miles. Groups limited to 14 with two guides; support includes water, sugar based snacks and blister plasters, typical ti..
June 2027
Walkers follow a circular 50 miles course from Grouse Hill, Fylingdales via the Cleveland Way along coastal cliffs through Robin Hoods Bay and Whitby, then inland across moor, woods and villages. Parking, four checkpoints, drop bags, water and a..
Guided, supported crossing of the North York Moors from Osmotherley to Ravenscar covering just under 39 miles of moorland and coast. Small groups with a maximum of 14 walkers are split by pace, with back up, checkpoints and supplied water, snacks..
Walkers tackle a 20 miles night trail from Goathland Village Hall across tracks, moorland and forestry, with GPX, trackers and refreshments at checkpoints.
July 2027
The event is a guided, supported crossing from Osmotherley to Ravenscar across the North York Moors, covering just under 39 miles. Small guided groups (max 14) travel by minibus to the opposite end and receive water, sugar snacks and blister plas..
Guided and supported crossing from Osmotherley to Ravenscar across North Yorks Moors moorland. The route is just under 39 miles, typically 15 to 18 hours, with two guides, minibus transfer, checkpoints, water, snacks and blister plasters.