Home › Self-Guided Walking Holidays › Lady Anne’s Way Overview

Lady Anne's Way Overview

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.

Holiday Includes
  • 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 24 hours a day.
Tour Availability

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


Accommodation is provided in carefully selected walker friendly B&Bs, Guest Houses, small Hotels and Inns along the route. All rooms are ensuite or have private bathroom. 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).

Not Included

Evening meals, packed lunches, drinks and snacks, travel insurance, travel to Skipton and from Penrith, souvenirs, laundry services, etc.

More Information?

For more information or to make an enquiry, please don't hesitate to call or email us.