Woods in the Chiltern Hills Ridgeway Walk. sunlight through beach trees


87 miles Moderate

A National Trail following the prehistoric route from Overton Hill in Wiltshire to Ivinghoe Beacon in Buckinghamshire. The Ridgeway forms part of the Greater Ridgeway linking the Dorset Coast to The Wash. It has been used as a path for at least 5,000 years. One interesting fact is that it passes through the grounds of Chequers Court, the UK Prime Minister's country retreat at the foot of the Chiltern Hills.


The highest point on the Ridgeway path is only 860 ft high at Uffington Castle, an Iron Age hillfort in Oxfordshire. It crosses both the Berkshire Downs and the Chiltern Hills and so there are a few steep sections, but on the whole the terrain is moderate. The path is well signposted with the National Trails’ acorn symbol.

The Ridge Way, National Trail, featured walk Walks With Williams
Enjoy a walking holiday across the historic Ridgeway National Trail


  • Day 1   Overton Hill to Ogbourne St George – 9 miles
  • Day 2   Ogbourne St George to Bishopstone – 9 miles
  • Day 3   Bishopstone to Letcombe Regis – 10 miles
  • Day 4   Letcombe Regis to Streatley/Goring – 15 miles
  • Day 5   Streatley/Goring to Watlington – 15 miles
  • Day 6   Watlington to Princes Risborough – 11 miles
  • Day 7   Princes Risborough to Wiggington – 13 miles
  • Day 8   Wiggington to Ivinghoe Beacon – 5 miles

The most popular direction to do this walk is from South to North, but if you would prefer to go from North to South then this can be easily arranged. Both ends of the walk are near mainline train stations in Swindon (for Overton Hill) and Tring (for Ivinghoe Beacon).


The price for this custom Chiltern Ridgeway walking holiday package is from £895 per person (based upon 2 people sharing). This includes:

  • Personalised itinerary for walking The Ridgeway on a self-guided basis over 8 days
  • 9 nights’ bed & breakfast accommodation on a double or twin room basis (this includes B&B for the night before you start and the day you finish)
  • Taxis for drop-off/pick-up where the B&B is not within easy walking distance of the Path
  • Baggage transfer for one bag per person between each night’s B&B
  • Advice on travel arrangements to and from the start and finish points
  • Ordnance Survey Explorer maps which can be downloaded onto the OS App
  • Harvey Waterproof Map for The Ridgeway
  • Kit checklist – covering boots & socks, clothes & waterproofs, and other useful kit
  • Helpline – you can call us at any time

Solo traveller, then price is £1190. This is because most B&Bs do not have single rooms and so will charge almost as much for one person as for two.

Key Information:

  • Time of Year: The Ridgeway hiking holiday can be done at any time of year, although if you choose to go between November and March then you will have to contend with the UK’s winter weather conditions and shorter daylight hours. Therefore, we would suggest that the best time to go is between April and October
  • Terrain: The terrain around the Ridgeway area of Buckinghamshire is moderate. For much of its length, the path is relatively level with a few steep climbs and descents. The walking surfaces
  • Way marking: The Chiltern Ridgeway walking route is well signposted with the National Trails’ acorn symbol.
  • Bed & Breakfast: We always aim to book good quality B&B accommodation as near as possible to the path. Despite the fact that The Ridgeway is a popular long-distance walk, there are not a huge number of B&Bs actually on the path itself or within easy walking distance. This means that sometimes the only option is to book B&Bs that are away from the path and arrange pick-up/drop-offs by taxi.
  • Refreshments: Compared with some other routes, The Ridgeway walking holiday route is actually quite good for places en route where you can get a cup of coffee (and maybe even a bacon butty or cake!) while not having to deviate from the path.

Whether these will be open depends upon the time of year, day of week and time you happen to be passing.


Booking the Chiltern Ridgeway walking holiday is easy. Start by filling out the enquiry form, and we’ll plan a bespoke route for you, before sending you a quote with all the details of your trip. Then, simply make your booking and enjoy your self-guided walking holiday in the English countryside!

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