Valentines on Win Hill Guided Walk

This Valentine’s Day walk will definitely warm the hearts of those wanting to get outside and beat the winter blues. Win Hill is one of the Peak District’s finest summits, high above the the Hope Valley.   If you are looking for great panoramas of the Peak District’s high edges, plateaus reservoirs and valleys, this the walk for you!  The walk starts and finishes near Hope and Castleton Villages, from the award-winning Bike & Boot Peak District Hotel.  Parking, a great hike, hospitality, and accommodation if you need it, are all available in one location – so perfect if you are visiting the area.

  • Distance: 7 miles/11.5km.
  • Ascent: 1211ft/369m of ascent.
  • Difficulty: Moderate. Easy to Moderate Pace
  • Great For: New and experienced hill walkers who are happy with ascents/descents on rocky paths.
  • Dogs:  Obedient dogs on leads are welcome.  See ‘Description’ section below.
  • Approx Timings: 0945 – 1500. Final confirmation when you book.
  • Start/Finish: Bike & Boot Peak District Hotel, Hope Valley, Peak District, S33 0AL
  • Location Map >

£45.00

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Description

Valentines on Win Hill Guided Walk

The Route: Our walk ascends through lanes and woodland, climbing onto high moorland before we ascend steeply on a rocky path to a distinctive summit – Win Hill Pike, standing proud above the valley (height: 1516ft/462m). This summit provides a true sense of space and position, high above the valleys and reservoir below. On clear days, panoramic vistas stretch towards Kinder Scout, the Derwent Edges, Mam Tor’s Great Ridge and the neighbouring summit of Lose Hill, with Ladybower Reservoir far below . A lovely descent gradually takes us down to the village of Hope – with views over moorland and valley all the way. There are toilets and a café in Hope too! Walking along lanes and through valley pastures, we eventually join the main road for a short walk along the pavement back to the hotel.

Bringing Your Dog?  Dogs are welcome on this route.  Please note, there are short road or lane sections, and there may be occasional stiles to cross along the route. Owners must take full responsibility for their pet, working within the conditions and requirements set down by the guide before the walk commences.   This includes:

  • Ensuring your dog is well-behaved and fully under your control at all times.
  • Ensuring your dog is on a lead (we are walking in areas with protected wildlife and livestock). We also cannot wait if your dog runs off.
  • You are responsible for clearing up dog waste on paths or pavements.
  • You are confident that your dog is properly equipped (water, treats, coat etc) for the walk and weather, and is able to manage the distance terrain and ascents/descents on the walk you have chosen.

 

Our recommended accommodation, Bike & Boot Peak District Leisure Hotel >,  where we park and start this walk, welcomes dogs.

Want to ask a question about this walk?  Please Contact Us >

Additional information

Walk Date

Sunday 14 February 2026

What’s included?

Included
  • Qualified Mountain Leader or Hill and Moorland Leader with Outdoor First Aid Qualifications.
  • Guiding throughout the day with briefing advice and support to ensure your safety.
  • Narrative on local points of interest, wildlife, geology, history and culture.
  • Optional photography of your day which can be shared with you.
  • The option of a free, return lift from a station or bus stop to the start of your walk to encourage sustainable travel. We can only arrange this if we have spare space in our vehicle and the pick-up point is reasonably close to your walk. Ask us when you book.
Not Included:
  • Parking or transport costs associated with your walk.
  • Essential walking kit or food.
  • Navigation equipment and maps for Navigation Courses (we will help if we have spares).

What to Bring

Here’s an Essential Kit Kist for all our walks >

Bringing Your Dog?  Dogs are welcome on this route.  Please note, there are short road or lane sections, and there may be occasional stiles to cross along the route. Owners must take full responsibility for their pet, working within the conditions and requirements set down by the guide before the walk commences.   This includes:

  • Ensuring your dog is well-behaved and fully under your control at all times.
  • Ensuring your dog is on a lead (we are walking in areas with protected wildlife and livestock). We also cannot wait if your dog runs off.
  • You are responsible for clearing up dog waste on paths or pavements.
  • You are confident that your dog is properly equipped (water, treats, coat etc) for the walk and weather, and is able to manage the distance terrain and ascents/descents on the walk you have chosen.

Meeting and Parking

We meet at Bike & Boot Peak District Hotel > Hope Road, Hope Valley, Peak District, S33 0AL.

  • We meet outside the rear entrance in the car park.
  •  The Hotel has toilets, a restaurant, café and accommodation.  Dogs are welcome.
  • To receive a 10 – 15%  Bike and Boot Discount* enter the promo code PEAKWALK when you book on line: Bike & Boot Booking > .
  • (*Discount may not available on Bank Holiday Weekends).

 

Please see a Google Map showing the Bike & Boot Peak District Hotel location  here>.

Coming by Bus or Train
We’re keen to support public transport use and reduce emissions. If you’re arriving reasonably nearby we’ll give you a free lift.  Just ask us when you book.

Facilities

Bike & Boot Peak District Hotel > where we meet has toilets, a restaurant, café and accommodation.  The hotel welcomes dogs.

Here are some other local villages and facilities, all within 10 minutes’ drive:   

  • Hope Station:  is less than 5 minutes’ drive or 15 minutes’ walk from Bike & Boot.  where we meet. A public bus service also connects the station and the hotel.
  • Hope:  This small village has toilets, limited shops, cafes, pubs, hotel and B & B’s. More About: Hope >
  • Castleton: This is a picturesque village below Mam Tor summit and The Great Ridge, with toilets and a Visitor Centre, cafes, restaurants, pubs, hotels, shops B and B’s and a Youth Hostel. There are also the famous Blue John Mines and caverns, and a castle.  More About Castleton >
  • Hathersage:  Hathersage is has toilets, a garage, shops, restaurants, cafes, hotels, pubs, B and B’s and a Youth Hostel. More about:  Hathersage >

 

See a map of the local area here >.

Walk Difficulty

This is a Moderate Walk. The pace will be fairly relaxed – an Easy to Moderate Pace.  Here is our walk difficulty guide >

Please Note:  There will be some steep ascents and descents on rocky paths.  It may be boggy in places if it is wet.

FAQs

We have created a separate page of the most frequently asked questions here >

Accommodation

Our Recommendation: 

  • Bike & Boot Peak District Leisure Hotel >
  • This is the hotel where we park and  start our walk.
  • We partner with Bike & Boot, an award winning leisure hotel in the Hope Valley that’s ideal for walkers! There’s a restaurant / breakfast, free hot drinks for guests, free cake at 4pm and free films three times a day. Also, a drying room for gear and free on-site parking too.
  • The hotel welcomes dogs.
  • To receive a 10 – 15%  Bike and Boot Discount* enter the promo code PEAKWALKING when you book on line: Bike & Boot Booking > .
  • (*Discount may not available on Bank Holiday Weekends).

 

Other Options:

Respect, Protect and Enjoy!

We all want to respect, protect and enjoy the fragile upland environments where we walk, so that they can be enjoyed by generations to come.  Following The Countryside Code really helps…

Respect:
  • Be considerate to those living in, working in and enjoying the countryside
  • Leave gates and property as you find them
  • Do not block access to gateways or driveways when parking
  • Be nice, say hello, share the space
  • Follow local signs and keep to marked paths unless wider access is available
Protect:
  • Take your litter home – leave no trace of your visit
  • Do not light fires and only have BBQs where signs say you can
  • Always keep dogs under control and in sight
  • Dog poo – bag it and bin it – any public waste bin will do
  • Care for nature – do not cause damage or disturbance
Enjoy:
  • Check your route and local conditions
  • Plan your adventure – know what to expect and what you can do
  • Enjoy your visit, have fun, make a memory
Want to know more?
  • Sustainability – our actions and fund raising to support the local environment, communities and economy.
  • Contact Us – ask a question or make a suggestion.