Lady Anne's Way Self Guided Walking Holiday

Holidays from 6 to 9 Days Walking, 100 miles, From £575 per person

Pendragon Casle

This self-guided walking holiday is along Lady Anne's Way, a 100 mile trail leading from Skipton in North Yorkshire to Penrith in Cumbria. The walk was devised to follow some of the routes Lady Anne Clifford took while travelling between her castles, and also to walk through the beautiful scenery of the Yorkshire Dales and Eden Valley. The route is one of great beauty, outstanding scenery and historical interest.

Starting from the magnificent Skipton Castle, the route heads to the River Wharfe and onto Grassington. From here the trail continues along Wharfedale before crossing the moor to Hawes in Wensleydale. Along the ‘High Way’ and into Mallerstang you pass the ruins of Pendragon Castle on route to Kirkby Stephen in the Eden Valley. From Kirkby Stephen you follow the direction of the River Eden to first the ruins of Brough Castle, and then north east to Appleby Castle. The route then continues to the extensive ruins of Brougham Castle, and the end of the trail in Penrith.

Each night on the trail you stay in a different location in prebooked selected accommodation, with breakfast provided. Your luggage is collected daily and moved to your next accommodation.

Book with Northwestwalks and you can be confident of a personal, professional and well organised service. You can be assured we select quality walker friendly accommodation and provide a reliable daily luggage transfer service, plus a holiday pack which includes route information, accommodation details, route map, guidebook and the reassurance we can always be contacted should you need assistance.

You can start your holiday on any date of your choice between April and October.
You can include rest days from £60ppn if required.
To book your holiday choose an itinerary that meets your requirements, then click Book Your Holiday

7 Nights/6 Days Walking
Lady Anne's Way self guided itinerary

  • 7 nights accommodation including breakfast

  • Baggage transfer along the route

  • 6 days walking

  • Total distance 100 miles

  • Average daily distance 17 miles

  • Shortest day 13 miles

  • Longest day 20 miles

  • Cost £575/person
    (single supplement* £210/person)

Click here to view Itinerary

10 Nights/9 Days Walking
Lady Anne's Way self guided itinerary

  • 10 nights accommodation including breakfast

  • Baggage transfer along the route

  • 9 days walking

  • Total distance 100 miles

  • Average daily distance 11 miles

  • Shortest day 6 miles

  • Longest day 15 miles

  • Cost £810/person
    (single supplement* £300/person)

Click here to view Itinerary

Holiday price - Our holiday prices are based on two people sharing a room.

*Single supplement - There are very few single rooms along the route and therefore the accommodation owners generally allocate a double or twin room for single occupancy. We can accommodate one single occupancy per booking for the average supplement of £30 per night. If you require additional single occupancy rooms, they will be charged at the extra cost incurred. This can be up to full double/twin room rate.

If you want to follow an itinerary that is not listed please contact us with your requirements.

Pendragon Casle

Tour availability
This walking holiday is available from April to October. You can book your holiday to start on any date of your choice.

Start of route
Skipton, North Yorkshire.

End of route
Penrith, Cumbria.

Direction of walk
South to North

Grade of walk

Generally this is a moderate route though some strenuous hill walking is encountered in the Yorkshire Dales.

The terrain varies from riverside paths, farmland, country lanes and lowland moors.

The route is not waymarked but it follows recognised footpaths. We recommend you are able to navigate with Ordnance Survey maps and a compass. A GPS is also a good backup device.

Holidays include

  • Carefully selected walker friendly accommodation.

  • Breakfast each day.

  • Luggage transfer between overnight accommodation.

  • Route information and itinerary.

  • Detailed instructions to find your accommodation.

  • Guidebook and Ordnance Survey maps.

  • Emergency contact

Not included in the price of your holiday
Evening meals, packed lunches, drinks and snacks, travel insurance, travel to Skipton and from Penrith, souvenirs, laundry services, etc.

Accommodation is provided in carefully selected walker friendly B&Bs, Guest Houses, small Hotels and Inns. We aim to book rooms with ensuite or private facilities every night, however in a few villages ensuite accommodation is limited and we may have to book rooms with shared facilities for one or two nights of your holiday.

Accommodation directions
We provide detailed instructions to find you accommodation.

Breakfast is included.
Packed lunches can be readily purchased from your overnight accommodation or local shop.
Evening meals can be purchased in local village pubs or overnight accommodation when a pub is not available.

Luggage transfer
For the duration of the holiday your luggage is transferred from accommodation to accommodation by a luggage transfer agent. Luggage allowance is 1 bag/person weighing not more than 20kg (44lbs).

Guidebooks and Maps
A guidebook and Ordnance Survey maps are included.

Emergency contact
We can be contacted 24 hours a day if required.

The weather in Northern England is varied. You should be prepared for all possibilities as weather, particularly in the hills, can change quickly. Weather statistics are available from the Met Office at

Good outdoor clothing and waterproofs are essential, please see equipmement list for further details.

Comfortable walking boots which provide good grip on multiple terrain and ankle support are recommended.

Please see equipmement list for further details

Some accommodation owners provide a laundry service for a small fee.

Burnsall Bridge

Lady Anne's Way is a 100 mile trail leading from Skipton in North Yorkshire to Penrith in Cumbria. The walk was devised to follow some of the routes Lady Anne Clifford took while travelling between her castles, and also to walk through the beautiful scenery of the Yorkshire Dales and Eden Valley. The route is one of great beauty, outstanding scenery and historical interest. The following is to provide further information about the route. Please note that all distances and heights are approximate and along with all the other information are provided as an aid to describe the route.

Skipton (height above sea level 140m) to Grassington (200m).
Lady Anne Clifford was born at Skipton Castle, now one of the best preserved medieval castles in England and fittingly the route begins at her birthplace. Skipton is known as the gateway to the Dales and has lots to offer, with cobbled streets and alleyways to explore, with plenty of shops and cafes to visit. Skipton castle is also worth a visit. After leaving Skipton, the first village on route is Embsay, famous for its steam railway. You continue across farmland and enter the Yorkshire Dales National Park. The next 50 miles of the Lady Anne’s Way are within the Yorkshire Dales, there is such variety to be discovered, lonely fells, idyllic riverside graze land, leafy woods, farmland and pretty villages with an interesting industrial past. The path climbs onto moorland and crosses Halton Edge (290m) before descending to the ruins of Barden Tower where Lady Anne often stayed throughout her life. The route then follows the banks of the River Wharfe to the picturesque, unspoilt village of Burnsall (150m). The route leaves the river to cross fields to Hebden and then Grassington. Grassington is a small, thriving town. It attracts many visitors with its cobbled streets and attractive buildings and once prospered from the lead- mining industry.

Grassington (200m) to Buckden (220m).
From Grassington you walk uphill to Capplestone Gate (512m) on Conistone Moor with vast views of Wharfedale, Bastow wood and Lea green. After the uphill trek it’s a gradual walk downhill to delightful Kettlewell (210m) which has a few shops and pubs. The route continues through fields to Starbotton, before following the River Wharfe to Buckden.

Buckden (220m) to Hawes (240m).
From Buckden the path climbs to the top of Stake Moss (558m) to a route once used by the Romans, and Lady Anne herself to visit her castles in the Eden Valley. The path is easy to follow and descends gradually to join a bridleway and a clear track to Cubeck and from there to Worton (200m). From Worton it’s on to Nappa Hall, a well preserved medieval building, where Lady Anne stayed one night. Other famous visitors include James 1, Sir Walter Raleigh and Mary Queen of Scots. Then it’s onward to Askrigg with shops, cafés restaurants. The painter Turner stayed at the King’s Arms and in the market place there is a commemorative seat for the travels he undertook in the 19th century, it is known as the Turner trail seat. Also, Crinkley House in Askrigg (230m) was frequently used in the television series ‘All Creatures great & small’. From Askrigg the walk takes you along Wensleydale valley. It is worth visiting Mill Gill falls, a few yards off route the waterfalls are a sight to see. Then it’s onward across fields to Hawes, a busy market town in Upper Wensleydale with lots of visitor attractions, cafes and shops.

Hawes (240m) to Kirkby Stephen (180m).
From Hawes there is a walk through fields to Appersett viaduct. You follow the River Ure to the ‘Highway’, where the path climbs to take this ancient high route over the fells from Wensleydale to Mallerstang valley. The Highway (highest point 500m) was used by the Romans. In the 18th century it was a packhorse route for goods from Wensleydale to Kendal and was also used by Lady Anne on her way to Pendragon Castle. There are superb views all around as a reward. While on the Highway there are deserted buildings to see, one being High Hall. The next point is to Hell Gill Bridge; look over the right side at its steep sided ravine. It is believed a highwayman on horseback jumped this gully to escape capture. The bridge also denotes the border between Cumbria and Yorkshire. The Highway descends, at the valley bottom, there is a sculpture called ‘Water cut’ by Mary Bourne and is known as the Eden Benchmarks. It is one of ten commissioned by East Cumbria Countryside Project. The route follows the river to Outhgill (250m) and Pendragon Castle. Locally it is believed the castle was built by Uther Pendragon, father of Arthur of the round table. Lady Anne restored the castle in 1660 and was a useful stopping point for her on the way to her castles in the Eden Valley. From the castle the route continues to Nateby village from where it’s a short walk to the market town of Kirkby Stephen.

Kirkby Stephen (180m) to Appleby-in-Westmorland (150m).
This section offers wonderful scenery and is steep with historical interest, with the ruins of Brough Castle, Ormside ‘Cross’ and church, ending in Appleby with its magnificent castle and churches. The path follows the river downstream, to your right there are views of Nine Standards Rigg in the skyline, then across fields to the outskirts of Winton village. Shortly after Winton you leave the valley of Mallerstang to begin your journey through the lovely Eden Valley. Passing the hamlet of Kaber, walk along Belah River with views to the red cliffs of Belah Scar. The next village is Brough Sowerby then to Church Brough (180m), where you can wander off route to visit the castle remains. Lady Anne’s Way takes you through the centre of Church Brough then through some fields to follow a good path, contouring Langrigg Hill to Flitholme. There is the option to visit Warcop village or continue along Lady Annes Way to Warcop Old Bridge. The track takes you along bridleways, hedge lined paths, riverbanks, and farmland to Little Ormside and Great Ormside. The church of St James in Great Ormside is rich in history and worth visiting if time allows. There is easy walking alongside the River Eden to Appleby. The castle restored by Lady Anne is now privately owned and is therefore not open to the public. However there is still plenty to see in Appleby and wherever you go there are references to Lady Anne. The church of St Lawrence holds the elaborate tomb of Lady Anne and her mother Margaret Countess of Cumberland. Appleby is extremely busy in early June with travellers and horse traders, it holds the biggest horse fair of its kind in the world.

Appleby-in-Westmorland (150m) to Penrith (140m).
This section is a low level route with splendid views, delightful villages and ancient ruins of Brougham Hall and Brougham Castle, just before reaching Penrith and the end of the trail. On leaving Appleby you continue through fields to the delightful village of Long Marton (130m). The church here was built in the 12th century on the site of an earlier wooden structure. Leaving the village it’s onward to Kirkby Thore, where there is the hall of medieval origin and a site of a Roman Fort. From here the path follows the River Eden to Ousenstand Bridge (100m) then continues to Crossrigg Hall, built in 1864 to a Jacobean design and retains some of its original features. It’s then Cliburn with its church standing in a prominent position above the River Leith. After Cliburn there is a section of road walking with a good grass verge if you prefer, with Whinfell Forest to your right. Then it is onwards to Pembroke House and then Brougham Hall. The ruins of Brougham hall are undergoing restoration. In the stables and carriage houses there is a craft fair and a café. From Brougham Hall your next landmark is Brougham castle. The castle is an extensive ruin and was built by Robert de Vipont one of Lady Anne’s ancestors. Lady Anne spent a lot of time here, her father was born here and both she and her mother died here. From the castle it’s a short walk to Penrith. In the centre of town is the market square, with a monument and clock tower marking the end of Lady Anne’s Way.


By train
Train timetables can be viewed and tickets purchased online at
Prices can vary greatly and reduced price ‘Advanced tickets’ are sometimes available and can be purchased from approximately 12 weeks prior to departure.
To Skipton
The train station in Skipton is a short walk from your accommodation.
From Penrith
The train station in Penrith is a short walk from your accommodation.

By bus Bus timetables are available to view online at

By Air The most convenient major International airport with rail links is Manchester Airport.

Please remember to
1. Keep the weight of your day pack and walking/hiking equipment to a comfortable weight for you to carry

2. Keep your suitcase/luggage under the maximum transfer weight (Maximum: 18kg (40lbs)).

The following checklist is an aid to help you with your packing
Walking/Hiking boots (worn in before your holiday)
Technical walking socks e.g. liner and thick outer socks
Trekking trousers (not jeans/denim)
Waterproof over trousers
Baselayer T-shirts and/or casual shirts
Fleece or warm jumper
Waterproof jacket
Spare warm layer (to carry in your rucksack)
Warm gloves
Warm hat
Rucksack (25 to 35 litres) and waterproof cover
Rucksack liner e.g. large plastic bag
Water bottles 1 litre (x2)
Basic First Aid Kit and personal medication
Insect repellent
Torch / flashlight

Spare Laces
Thermos flask for hot drinks
Antibacterial hand wash/wipes
Camera, film, batteries
Trekking poles

Customer reviews

Hello NWW, Just wanted to say how much we enjoyed the walk, weather best ever….Many thanks again for a successful and enjoyable walk. Ruth and Linda, UK, Lady Anne's Way Self-Guided, 2015

To contact Northwestwalks
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