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© 2026 Celtic Trails Walking Holidays. A company registered in England and Wales under number 07736096. All rights reserved. Registered address 5 Ashweir Court, Tintern, Wales, NP16 6SE United Kingdom.

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Walking Holidays
About Us
Back to walkCleveland Way
ItineraryCLV2
Vibrant purple heather blooms on a scenic walking trail in Celtic Trails, exploring picturesque landscapes and coastal views.

CLV2 · Cleveland Way · England

Helmsley to Filey

Difficulty
Moderate, Moderate to Challenging
Distance
109.4 miles
Walking
9 Days
Bed & Breakfast
10 Nights
Grade
Classic
Dog Friendly
No

Book Now

From £1370 per person
Book

Overview

  1. Day
    1
    Arrival Day
    1. HelmsleyHelmsley
  2. Day
    2
    Helmsley to Sutton Bank
    10 mi · 16.1 km
    1. Helmsley to Sutton Bankplus 2.6 miles down to accommodation
    2. KilburnKilburn
  3. Day
    3
    Sutton Bank to Osmotherley
    11.25 mi · 18.1 km
    1. Sutton Bank to Osmotherleyplus 2.6 miles back up to the path
    2. OsmotherleyOsmotherley
  4. Day
    4
    Osmotherley to Clay Bank Top
    11 mi · 17.7 km
    1. Osmotherley to Clay Bank Top
    2. transfer
    3. Kirkby-in-ClevelandKirkby-in-Cleveland
  5. Day
    5
    Clay Bank Top to Roseberry Topping
    13.75 mi · 22.1 km
    1. transfer
    2. Clay Bank Top to Roseberry Toppingplus 0.5 miles to your accommodation
    3. Newton under RoseberryNewton under Roseberry
  6. Day
    6
    Roseberry Topping to Saltburn by Sea
    10.5 mi · 16.9 km
    1. Roseberry Topping to Saltburn by Seaplus 0.5 miles back up to the path
    2. Saltburn by SeaSaltburn by Sea
  7. Day
    7
    Saltburn by Sea to Runswick Bay
    12.2 mi · 19.6 km
    1. Saltburn by Sea to Runswick Bay
    2. Runswick BayRunswick Bay
  8. Day
    8
    Runswick Bay to Robin Hood's Bay
    15.2 mi · 24.5 km
    1. Runswick Bay to Robin Hood's Bay
    2. Robin Hood’s BayRobin Hood’s Bay
  9. Day
    9
    Robin Hood's Bay to Scarborough
    15 mi · 24.1 km
    1. Robin Hood's Bay to Scarborough
    2. ScarboroughScarborough
  10. Day
    10
    Scarborough to Filey
    10.5 mi · 16.9 km
    1. Scarborough to Filey
    2. transfer
    3. ScarboroughScarborough
  11. Day
    11
    Departure Day
    Travel day
Overnight locations and transfer arrangements may differ slightly from those shown, depending on availability.

What's Included

  • Good standard accommodation at a mixture of guesthouses, farmhouses, local inns and B&Bs with en-suite or private facilities wherever possible
  • Breakfast
  • Luggage transfers
  • Personal transfer between accommodation and path that form a part of our standard package
  • Route planning
  • Walk pack including Trail Guide and mapping, itinerary, accommodation directions and route notes, lunch and dinner information, restaurant recommendations and holiday planning details

Extras

Rest days/additional nights:

  • Prices from £150 per room per night
  • Recommended location: Helmsley.

Upgrade options:

  • Speak to our team to discuss upgrade options for this itinerary

Supplements:

  • Weekend supplements may apply in: Saltburn-by-the-Sea
  • Short notice bookings and Bank Holidays may incur additional charges

Walk Pack postage:

  • to UK: included in price
  • to Europe: £25 per pack
  • to Rest of World: £30 per pack

Extra Walk Packs:

  • Please see here for full details and supplements

From Pricing

Plan your trip

1 Jan 2026 – 31 Dec 2026

£1,370pp

Per person, based on two people sharing

Solo traveller
£2,050
Single occupancy
£1,930
Rest days£150per room, per day
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