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Shakespeare's Way Highlights  The Natural Adventure Company 3

Shakespeare’s Way Highlights: Stratford-upon-Avon to Oxford


The Shakespeare’s Way is a 240 km long-distance walk from Stratford-upon-Avon to the Globe Theatre in London, which the great playwright partially owned and where his plays were performed. On this 6-days walking adventure, you will follow the route that the Bard of Avon may have taken when he left his birthplace between 1585 and 1588. Walk the best sections of the route between Stratford-upon-Avon and Oxford, passing through some charming little towns and notable landmarks, including the Rollright Stones, Chipping Norton and Woodstock.

Click to view map


Day 1: Arrival Stratford-upon-Avon

Arrive in Stratford-upon-Avon, the birthplace and gravesite of William Shakespeare. Set in the beautiful rural Warwickshire countryside on the River Avon banks, it is a beautiful town and home to one of the world’s great theatrical ensembles, the Royal Shakespeare Company.

Day 2: Stratford – Shipston-on-Stour | 17 mi / 27.2 km

Enjoy your hearty breakfast and cross the River Avon and the River Stour to leave Stratford. Follow the river banks for the first part of the trail, across farmland and thatched cottages, watermills and village churches. The path then brings you to Shipston-on-Stour’s market town, known in Shakespeare’s time as Sheepstown.

Day 3: Shipston-on-Stour – Chipping Norton | 14 mi / 22.4 km

Today, you pass close to the Rollright Stones, an ancient site located on the Oxfordshire/Warwickshire border. The complex consists of three main elements, the King’s Men stone circle, King Stone, and the Whispering Knights. Arrive at Chipping Norton, once a centre of the wool industry and trade, retains many elegant buildings from that era and has evolved into a thriving and vibrant local economic and cultural centre. Overnight Chipping Norton.

  • Walking for the day: 14 mi / 22.4 km
  • Accommodation: Kings Arms B&B*** in Chipping Norton

Day 4: Chipping Norton – Woodstock | 16 mi / 25.6 km

Walk to Woodstock. Follow the Glyme valley through Ditchley Park and past Blenheim Palace to Woodstock’s picturesque town, which originated as a settlement within the Royal Forest of Wychwood. Blenheim Palace was built between 1705 and 1724, as a gift to John Churchill, the 1st Duke of Marlborough in appreciation of his defeat of the French and Bavarians at the Battle of Blenheim. A UNESCO world heritage site, the architect was Sir John Vanbrugh and the landscaped gardens were designed by Capability Brown. Overnight Woodstock.

  • Walking for the day: 16 mi / 25.6 km
  • Accommodation: Punchbowl Inn*** in Woodstock

Day 5: Woodstock – Oxford | 11 mi / 17.6 km

Let the days start with a visit to Bladon, where Sir Winston Churchill is buried in St. Mary’s churchyard. Cut across the country to the Oxford Canal before following the River Thames into Oxford, the home to the oldest university in the English-speaking world. Oxford unquestionably ranks among England’s most beautiful cities with its honey-coloured colleges arrayed in splendour beside the river. 

Day 6: Departure

Extra night available upon request.

What to Expect


Accommodation is in nice 3-star hotels, B&Bs, guesthouses and inns, in double or twin private en-suite rooms. We have carefully hand-picked all places and regularly monitor their quality. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Click to view our default hotels for this trip

*Hotels are subject to availability. In case a hotel is fully booked for your desired dates, we will replace it with a property of equal standard. We will provide full accommodation details upon booking confirmation.


Accommodation is on a bed & breakfast basis. Picnic lunches are optional at an extra charge and can be ordered locally. You can have dinner at your hotel or at nearby restaurants.

Difficulty & terrain

Variable but easy to moderate – nothing strenuous if you can walk the distances concerned (read more about difficulty grades). We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime.

When to go

This trip is available from mid-April to mid-September. Accommodation will be difficult to obtain on UK bank holidays unless booked well in advance.

The flexibility of self guided holidays means that there are no fixed dates, and you can start your trip on any date during the season.

All 2022 departures are now fully booked, we do accept requests for 2023.

Getting there

Up-to-date travel advice on the United Kingdom is available here (Canadian citizens) and here (US citizens).

Click to view travel options and route planner

By plane

Our recommended airport for this tour is Birmingham.

By train or bus
  • Stratford-upon-Avon is easily reached by train from London Marylebone to Leamington Spa with Chiltern Railways (approx. 1 h 15 min), following by bus (40 min. with Stagecoach Midlands). The train journey from Birmingham Airport to Leamington Spa station takes 25 minutes.
  • From Oxford, you can take the train to Birmingham Airport (approx. 1 hour with CrossCountry); or to London Paddington (approx. 50 min. with Great Western Railway).



  • 5 overnights with private bathrooms as detailed in the itinerary
  • 5 breakfasts
  • Luggage transfer when changing hotels (one piece of luggage per person, max 20 kg)
  • Detailed route notes and maps (1 set per booking)
  • 24/7 phone assistance by our local office/representative


  • Airfare and connecting land transfers
  • Lunches, dinners, drinks and snacks
  • Travel insurance (required – get a quote online)
  • Personal expenses
  • Any items not specifically mentioned as included in the programme

Options, extras & supplements

  • Single room supplement for members of a group – upon request only
  • This holiday is available for solo travellers upon request only; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)