Self Guided Walking Holidays & Cycling Holidays

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Shakespeare's birthplace


  • Immerse yourself in the historic towns of Stratford-upon-Avon and Oxford
  • Walk in the famous footsteps of William Shakespeare
  • Visit the spectacular Blenheim Palace, a UNESCO World Heritage Site
  • Explore the Bronze Age Rollright Stones
  • Experience the beauty of the Cotswold Countryside

Follow in the footsteps of the bard as you walk on The Shakespeare’s Way from Stratford-upon-Avon to Oxford. William Shakespeare himself would have walked this trail between his birthplace in Stratford-upon-Avon to the City of London.

Your journey starts in Shakespeare’s birthplace, Stratford-upon-Avon, a medieval town sitting proudly on the banks of the river Avon. Immerse yourself in Shakespeare’s life and legacy by visiting the many sites linked to the famous poet and playwright.

From Stratford-upon-Avon the walk heads south along the valley of the River Stour into the beautiful rolling hills of the Oxfordshire Cotswolds. Sprinkled with quaint Cotswold towns of Chipping Norton and Woodstock the Cotswolds are a walkers paradise.

Blenheim Palace, a UNESCO World Heritage site, is another highlight of this relaxed walking holiday through the English countryside.

The University City of Oxford is where your walking holiday on Shakespeare's Way comes to an end. Also known as ‘The City of Dreaming Spires’ due to the beautiful architecture of its college buildings, Oxford is a delight. We would recommend that you spend a few extra days in this wonderful city.

Our walking holidays on the Shakespeare's Way include hand-picked overnight accommodation in high quality B&B’s, country inns, and guest houses, daily door to door baggage transfer, a comprehensive guidebook, detailed map and information pack as well as emergency support.

This is a general stage by stage guide. For all the available day by day itineraries, please see the options on the right.

Arrive in Stratford-upon-Avon

The walk starts in Stratford-upon-Avon, a town steeped in history and culture where Shakespeare was born in 1564. You may want to add an extra night at the beginning of the walk to explore the many places associated with Shakespeare such as the Royal Shakespeare Theatre, The Shakespeare Centre and take the time to visit the five houses in and around Stratford-upon-Avon connected to the famous playwright and his family. Stratford-upon-Avon is easily accessible from London in around two hours.

Stratford-upon-Avon to Shipston-on-Stour – 17 miles

Leaving Stratford-upon-Avon you cross the beautiful River Avon and the River Stour whose green and lush valley you follow for the first part of the trail. Walk through patchwork farmland with high hedgerows and pass thatched cottages, watermills and scenic churches. There are plenty of places to stop and admire the views. The path then brings you to the market town of Shipston-on-Stour. In times gone by it was known as Sheepstown and held regular livestock markets for local farmers.

Shipston-on-Stour to Chipping Norton – 14 miles 

From Shipston-on-Stour the walking is relatively easy underfoot. Leaving the River Stour behind you, the climb up from the valley is worth it for the stunning views from the top.

Make time along the way for a short detour to visit the Rollright Stones an impressive and ancient Bronze Age collection of standing stones, the Kings Men stone circle, the King Stone, and the Whispering Knights stone. 

The welcome sight of Chipping Norton soon comes into view in the distance as you walk down towards Little Rollright Church. Chipping Norton is known as the ‘gateway to the Cotswolds’ and is another bustling yet charming market town. Explore the medieval architecture or browse the many small gift shops.

Chipping Norton to Woodstock – 16 miles

Fantastic walking today! Leave Chipping Norton and follow closely what was the route of the old London Road. The trail joins the River Glyme for a short while and passes through the Glyme Valley Nature Reserve.

The walk takes you through ancient woodland carpeted with flowers and through the pretty villages of Glympton and Wooton.

As you come into the beautifully manicured Blenheim Park you will catch your first sight of Blenheim Palace and the immaculate gardens landscaped by Capability Brown. Why not add an extra night in Woodstock for a leisurely visit to Blenheim Palace and Gardens.

Woodstock to Oxford – 11 miles

Almost straight away you come across the village of Bladon where a wander through the churchyard will reveal the final resting place of  Britain’s greatest statesman Sir Winston Churchill.

Grassy tracks through broadleaf woodlands and gentle meadows bring you to the Oxford Canal with its colourful narrowboats and bustling river life.

Following the river brings you to the historic City of Oxford with its many attractions and world renowned university, a great place to end your journey and spend some time sightseeing and reflecting on your journey.

Departing Oxford

Onward travel from Oxford is easy with regular trains to London Paddington (1hr), Birmingham (1hr 30mins) and other UK destinations. There are also regular buses to London and surrounding airports.


One of the highlights of this tour is the high standard of the accommodation. We specifically choose the Inns, Guesthouses and B&B’s to ensure that you enjoy every minute of your stay.

They all offer a warm welcome to walkers, traditional hospitality and delicious local food. We always try and book your accommodation as close as possible to the line of the trail.

Occasionally, in busy summer months walkers may need to venture a mile or so off the trail as the availability of quality accommodation can become scarce.

Please note that unless you plan to stay in Stratford Upon Avon for two nights, it is best to avoid starting on a Friday/Saturday night. Most accommodation providers in the area will only allow two night stays at the weekend which makes bookings more restrictive for us.

Single Rooms

If you require single rooms we would be happy to accommodate you although there is a single room supplement payable.


A hearty breakfast is included each morning. Lunch and dinner are not included, so you are free to choose from the available options. Most accommodations are more than happy to provide a packed lunch - this can be booked on arrival. Dinner is available either at your accommodation or nearby pubs or restaurants.

Walking Direction

We can offer this itinerary in either direction but the book is published from North to South, Stratford-upon-Avon to Oxford.

Additional Nights and Extensions

Many of our clients choose to add extra nights along the walk to sample more of the wonderful walking and attractions available on the Shakespeare Way. Extra nights can be added anywhere along the walk although we would recommend Stratford-upon-Avon, Woodstock (for Blenheim Palace) or Oxford as there is plenty to keep you busy on a rest day.

Fewer Nights

If you wish to reduce the number of nights we can tailor your trip to your requirements.

Tailor Made Holidays

We are always more than happy to tailor our standard itineraries to suit. Just let us know what you would like and we will be happy to arrange a tailor made walking holiday.


This route is graded as moderate, it is mainly walking on existing pathways, bridleways and some minor roads.


The route is waymarked by post with small plastic roundels or stickers with the Shakespeare Way logo and a yellow or blue arrow. You will also have access to the Macs Adventure Smartphone App enabling you to follow the route using your phone’s GPS so using this combined with the provided route notes and maps means you should have no problems finding your way.

Solo Walkers

We welcome solo walkers on Shakespeare's Way although you should, of course, take extra care in the outdoors when walking solo. A supplement will apply to baggage transfers.


A hearty breakfast is included each morning. Lunch and dinner are not included so you are free to choose from the available options. Most accommodations are more than happy to provide a packed lunch - this can be booked on arrival. Dinner is available either at your accommodation or nearby pubs or restaurants.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.  Please ensure that you do not bring more than one bag of 20kg as if this occurs, the luggage transfer company will ask you to pay an additional fee (approx. £5.00 per day, per bag). This additional payment, should it be necessary, needs to be made locally to the driver and in cash.

It is also very important that your bag is clearly labelled (and any additional bags). If they are not labelled we cannot guarantee that they will reach you at the next accommodation.

If you are travelling from far afield and do have more than one bag it is possible to arrange for the extra luggage to be stored whilst you are on the tour for a fee of £25 per bag. These additional bags would be picked up from your accommodation at the start point of your tour and dropped off wherever you finish depending on the itinerary you are doing. Please contact us if you are interested in this option.on.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

General Information

The distance and ascent/descents are approximations of the recommended routes.  Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen.  Your information pack has a detailed equipment list which includes standard  walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Getting to Stratford-upon-Avon

By Car: We don't recommend that you drive to Stratford-upon-Avon as long term parking is expensive. There is limited unsecure on street parking in the outlying residential areas.

By Train: There are regular direct trains from London Marylebone to Stratford-upon-Avon (2 hrs 20mins) and Brimingham (1hour). Manchester is also accessible by train (3hrs).

By Coach: You can get to Stratford-upon-Avon by coach from London Victoria (3.5hrs)  and Birmingham (1hr) 

Onward Travel from Oxford

By Train:  There are regular direct trains to London Paddington (1hr 15mins), Birmingham (1hr 40mins) and Manchester (3hrs)

By Coach: The Oxford Tube coach service runs 24hrs a day 7 days a week from Oxford into central London (2hrs). There are also regular coach services to other destinations such as Birmingham (2hrs), London Heathrow Airport (1hr 40mins) and London Gatwick Airport (2.5hrs)


  • Bed and breakfast in comfortable B&B's
  • Door to door baggage transfer.
  • A detailed info pack and guidebook
  • Access to the Macs Adventure Smartphone App
  • Emergency telephone support from our office in the event of a problem


  • Lunches, dinners, snacks and drinks
  • Entrance fees (where applicable)
  • Travel Insurance
  • Transport should you need to skip a stage

We are often asked the following questions and hope that you will find the answers useful.
Please don’t hesitate to contact us for more advice or specific questions about the walk.

How fit do I need to be?

The Shakespeare's Way is an easy and accessible walk. That said there will be a number of ascents and descents - most noticeably where the path crosses river valleys.  It helps to have done some multi day walking before and regular cardio vascular exercise prior to your holiday will increase your fitness levels and therefore your enjoyment of the walk.

How do the baggage transfers work?

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 15kg per person.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as this route is very popular. Given its proximity to London and the more populated areas in the South of England the trail can get busy - especially in the summer montrhs. To ensure you have quality accommodation, on or near to the trail its best to book as soon as you know your available dates.   

What personal equipment do I need?

You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc. You can download a full equipment list from the downloads page of our website. 

When is the best time of year?

This walking holiday can be enjoyed from March to October.  Summer can be hot in the South of England and very busy especially over the school holidays.  We would advise walking in the Spring to see the wild flowers that boarder the fields you walk through.

Am I able to take my dog?

Unfortunately we are unable to accommodate walkers with dogs as many of the accommodation providers we use do not accept pets.

What happens if I can’t walk a stage?

You can use public transport or local taxis to continue to your next overnight stop. In some cases the baggage transfer service that takes your bags on to your next accommodation may be able to assist. Our office can assist with helpful advice should you need to arrange transport for yourself or anyone in your party.


Shakespeare did not walk this way!


This was my second Mac's walking tour, the first being the Ridgeway a few years ago. Overall we enjoyed ourselves but did not enjoy this walk as much because much of the walking on Shakespeare's way is through fields which having just been ploughed makes quite difficult walking terrain. On at least two occasions the trail takes hikers up one side of a substantial hill and then down the other - I feel that travellers to London in Elizabethan times would have preferred to follow streams and avoid arduous hill climbing. Furthermore the trip was marred by two items. Firstly, following the "Shakespeare's Way" book (see next paragraph) we became lost several times which on two days extended the time and distance beyond what was comfortable. Secondly the B&B accommodations, not unexpectedly, made no provision for evening meals. However in at least one village there was no really suitable location for dinner within reasonable walking distance, given that we had already walked 12 miles that day. The pre-departure information pack lacked a map. I was told this was not required as the book provided was excellent. In fact I found it out of date (at least three years since revised) and inaccurate in several places, often confusing to follow and to relate to actual physical locations. A detailed (e.g. OS) map should always be provided for hikers. Additional information regarding places to stop for lunch or interesting diversions would be appreciated. I tried to use the Mac's Adventure app and downloaded it however could not find my particular tour on it and was subsequently told that it really only applies to international tours so no help at all really. The accommodation consisted of two very fine pubs, a reasonable but not exceptional hotel in Oxford and several barely acceptable B&B's. So, all in all and average score. Mac's organisation during the trip was faultless. It is always comforting to find our luggage has arrived before us.

Wizard of Oz

Melbourne, Australia


Walk with the open guidebook in your hand


The trail from Stratford to Woodstock was occasionally difficult to follow from the guidebook. More trail markers are needed. The two-mile stretch past Rollright Church leading to Chipping Norton was especially difficult to follow. The walk from Woodstock to Oxford was quite pleasant, the best part of my 58-mile walk.

Navigator Bob

Seattle, WA, USA

Shakespeare's Way


We walked Shakespeare's Way from Stratford to Oxford. It entails beautiful countryside, pretty villages, and some historic sites (most notably, Blenheim Palace, Bladon, and the grounds of Ditchley Park). As always Macs did a fine job organizing accommodation, communicating with us, and arranging luggage transport. Our lodging was average at one site (White Bear in Shipston), above average elsewhere, and truly exceptional in a couple of cases. The walk goes through rolling countryside, with no terribly demanding hills, and lots of river views (Avon, Stour, Glyme, and Thames). The path is not as well-maintained or signposted as other long-distance walks we have done in England--there are a few points where following the path is challenging, and quite a few brambles and spots with waist-high grass or crops. At a number of points, after making a turn (following our guidebook), we said "That would have been a good place for a sign post." And at Little Rollright, the path has apparently been rerouted, but, in the absence of path markers, if a couple of young locals had not taken initiative to mention it to us, we might well have become lost (as numerous others have, according to stories we heard at a B&B). The message is this: Be sure to take a good guidebook and/or map. A number of landmarks, bridges, and gates can require a sharp eye to spot, due to overgrown grasses and brambles. Lots of solitude on this walk--in about 60 miles we did not meet a single person walking Shakespeare's Way; our only companions were the occasional locals walking a dog. A tip: If you've not seen it, book an extra day in Woodstock to spend a day at Blenheim Palace--Churchill's birthplace, with exceptional gardens and woods, and good historical stuff. And of course a day in Oxford is always good too. Another good walk with Macs.

Ken & Dave



Great holiday walking the Northen half of Shakespeare's way


Like always the organisation by Macs was faultless, great accommodation and superb luggage transfers. The walk itself is a challange, my wife and I are experienced walkers and have done many over the years. Section of this walk lack way marking and quite a few of the paths are vertually inpassable, due to time of year ( June ) rights of ways are blocked due to crops requiring walkers to walk around the edges of the fields, this is the right thing to do but the fields are massive and quite a few miles are added to the walk. Not gone off track on a walk for many years until this walk, even with the comprehensive guide book and OS maps we got it wrong a few times,again adding mileage. Having said all that we had a great time but be aware it's not a walk for novices and if this route is to be promoted then both Warwickshire and Oxfordshire need to maintain the route to a far better standard.

Lost again



Beautiful Walk through Lovely Countryside


We completed this short (5 day trek) really as preparation for a longer trek in May. It met our requirements, but it proved to be far more. We had, varied walking in lovely Middle England countryside, historic buildings, country estates, beautiful villages, thatched and period houses, etc. A real joy!

Bob & Heather

North Wales




All the accommodation was excellent. So much so it would be difficult to pick which was the best. The luggage service was excellent as well as it was waiting for us at each location when we arrived. I would definitely recommend taking an OS map of the route as some of the guide book can be a little difficult to follow.

The Walking Manc



An interesting walk in the countryside


The overall trip was wonderful. The accommodations were all well done. Can't beat the Full English Breakfast. All of the hosts were professional and engaging. The guide book was not the best. Descriptions were vague. Some directions were just not right. Granted the hike is not a popular as the Hadrian's Wall walk or the Cotswold Way but the guide book needs to be re-examined. Certain areas of the trail were not well marked. That being said, loved the trip. We are planning the next Macs Adventure.




A walk into History


As usual, very well organised tour by Macs. Great landscape, great accomodation, a walk back into history. A Map and the guide book are essential, as part of the Trail are not well marked. Very muddy in parts, due to the weather, but then, that can`t be blamed an Macs ;-)


Eimke, Northern Germany


A Great Walk


Following Shakespeare's Way from Stratford on Avon to Oxford proved an excellent way to appreciate the English countryside. Our itinerary & instructions well suited our needs. Though the prolific summer growth obscured the way markers a few times, we were able to problem solve & were successful.The weather was perfect. Our accommodations were varied, interesting and very comfortable. Hosts were also helpful, when needed. We enjoyed quintessential English scenery, villages, hamlets...& especially the locals. The country pubs too! We're very proud of our accomplishment!

The Robust Ramblers

Vancouver, Canada


Great Trip!


This trip was great. It was like a puzzle I had to solve, using the guide book. The scenery was great and there were lots of small villages to visit along the way. An extra night in Woodstock to explore Blenheim Palace was definitely worth it. A highlight of the trip!


Washington, DC


Shakespeare's Way

4.3 11


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