Supported multi-day challenge events on the UK's most beautiful national trails · 2027 dates now open
★★★★★ 5.0 on Google · info@endurotrek.co.uk
HOME / CHALLENGES / CLEVELAND WAY
ADVENTURE 2027
CLEVELAND WAY
Purple heather, big skies, then the sea: 109 miles from Helmsley to Filey in four unforgettable days: a supported challenge event with checkpoints, support staff along the route and camp each night.
North Yorkshire
4 days · 3 nights
Camping included
Enjoy · Endeavour · Endure
DATES
6–9 May
2027, Thu–Sun
DISTANCE
109 miles
24–31 miles a day
DURATION
4 days
3 nights camping
START
Helmsley
Castlegate, YO62 5AB
FINISH
Filey
Sun 9 May
YOUR LEVEL
3 options
Enjoy to Endure
— OVERVIEW
Moor to sea
Purple heather, big skies, then the sea. In four days you'll journey along the whole Cleveland Way National Trail. You start in the market town of Helmsley and cross the open tops of the North York Moors. Then you reach the coast and follow the cliff path through Staithes, Whitby and Scarborough to the finish at Filey.
It's 109 miles of wild moorland, fishing villages and sea views, with checkpoints and support staff along the way and evenings at camp. You'll feel proud of this one for a long time.
North York Moors
Filey
2027 · 6–9 MAY
Cleveland Way
109 miles · 4 days · 3 nights
Pay deposit
Full balance due 12 weeks before the event
£75
Pay in 3 interest-free with PayPal
Choose PayPal at checkout
Pay in full
All done in one go
£429
✓ 3 nights' camping, tent provided
✓ Hot breakfast & packed lunch daily
✓ Checkpoints & medical support
✓ Baggage transfers
★★★★★ 5.0 on Google
Questions or a group booking?
info@endurotrek.co.uk
Subject to PayPal's approval. UK residents aged 18+. Pay in 3 is an unregulated credit agreement. Missing a payment could affect your ability to borrow in future.
— ROUTE & ITINERARY
Four days, 109 miles
DAY 1
Start: Helmsley
Leave Helmsley and head up onto the western edge of the North York Moors, passing Osmotherley.
26
MILES
DAY 2
Day 2: Cleveland Hills
The big day. You cross the high moorland escarpment, with huge views, and drop down to the sea.
31
MILES
DAY 3
Day 3: Moors to coast
Cliff tops, via Staithes and Whitby.
28
MILES
DAY 4
Finish: Filey
The last coastal miles, via Scarborough, to the finish at Filey.
24
MILES
— WHAT'S INCLUDED
We handle the logistics. You enjoy the journey.
✓
Expertly coordinated challenge
Support staff throughout the 109 miles, so you can focus on the views
✓
3 nights' camping
Well-equipped campsites with hot showers and fresh towels each day
✓
Hot breakfast & packed lunch
Every trekking day
✓
Official checkpoints
Complimentary drinks and snacks at key points
✓
Dedicated medical support
Professional assistance throughout the challenge
✓
Baggage transfers
Your kit taken to each stop – for Enjoy and Endeavour
✓
Personalised finishers keepsake
A personalised keepsake of your adventure
✓
Upgrade your stay
Shepherd's hut where available*
NEW FOR 2027
✓ 2-person tents provided: just bring your sleeping bag
✓ Sleeping mats for extra comfort
*Upgrade costs vary depending on booking and challenge.
— YOUR LEVEL
Same route. Your adventure.
Enjoy
AT YOUR OWN PACE
We move your main bag. A brilliant first adventure.
Carry: day essentials
Endeavour
A STEP FURTHER
Carry more of your own kit for a real sense of self-sufficiency.
Carry: 10kg+ plus food & water
Endure
THE FULL EXPEDITION
For experienced trekkers: everything you need on your back.
Carry: 15kg+ plus food & water
— FUNDRAISING
Walk the moors for a cause you love
1
Book your place
Pay your registration fee and look out for your confirmation email.
2
Pick your charity
We'll notify them, and they'll contact you to support your fundraising.
3
Start fundraising
Set up a page on JustGiving or GoFundMe and share it.
Charity places: pay a £75 registration fee with a fundraising target of £799, pay a £225 registration fee with a lower fundraising target of £499, or pay the full event price (this varies by event) and raise whatever you can. Raise at least 50% of your target 4 weeks before the event start date. *subject to change
OUR CHARITY PARTNERS
— TRAINING & KIT
Arrive ready to enjoy it
— FAQS
Good questions
Where does the challenge start and finish?
We start at 07:30 on Thursday 6 May 2027 in Helmsley (Castlegate, YO62 5AB) and finish in Filey on Sunday 9 May.
How does paying in instalments work?
Choose PayPal at checkout and select Pay in 3. PayPal splits the cost into 3 interest-free monthly payments, and your place is confirmed straight away. Subject to PayPal's approval, UK residents aged 18+.
Which challenge level should I choose?
Choose Enjoy if it's your first multi-day adventure: we move your main bag and you carry just your day essentials. Choose Endeavour to carry 10kg+ plus food and water (baggage transfer is available on Endeavour too), or Endure to carry 15kg+ for the full expedition. Everyone walks the same route and shares the same camp.
Is the deposit refundable?
Registration fees and deposits are non-refundable. See our Terms.
How do I pay?
Choose what suits you: secure your place with a £75 deposit, pay £429 in full, or pay in 3 interest-free with PayPal.
Is it a guided walk?
No. It's a supported challenge event. You walk the trail at your own pace, with checkpoints offering drinks and snacks and support staff throughout the route.
Do I need to bring a tent?
No. New for 2027, 2-person tents and sleeping mats are provided. Just bring your sleeping bag.
Can I fundraise?
Yes. Choose a charity after booking, or walk for one of our charity partners. Charity places: pay a £75 registration fee with a £799 fundraising target, pay a £225 registration fee with a lower fundraising target of £499, or pay the full event price (this varies by event) and raise whatever you can. Please raise at least 50% of your target 4 weeks before the event start date. *subject to change
