Stratford to Oxford Walk

This independent linear walking holiday takes in some England's finest historic sights! Starting in the achingly creaky halftimbered town of Shakespeare's famous Stratford Upon Avon, you flirt the northern fringe of the Cotswold Hills to arrive in Chipping Norton, an attractive 15th century wool town, where you’ll spend the night. From here, it's off through bluebell-filled woods to diminutive Woodstock village where Churchill's birthplace, Blenheim Palace is now a UNESCO-listed heritage site, and one of the loveliest country houses in England. Your final stretch takes you to Oxford's legendary dreaming spires where no visitor can fail to be inspired by the botanical gardens, Bodleian library and dozens of world-famous historic colleges.

Freedom and flexibility have been built into every stage of this holiday, meaning you can add in extra nights en route, or shorten the trip to suit busy diaries. On most days, the walks can be shortened by using local taxis (we arrange for a small supplement) and we've left all meals flexible as there are so many options at every stage of your route. You also have the choice between friendly, great value B&Bs or more luxuriously appointed hotels.

Detailed Itinerary:

Day 1 - Arrive in Stratford
The Royal Shakespeare Company is the most famous theatre company in the world - why not take in a show? You spend two nights here.

Day 2 - Discover Stratford 5km/3mi/2hr
Visit Shakespeare's birthplace, Holy Trinity Church where he is buried, and wander the curio shops that line Stratford's narrow streets. This afternoon, enjoy a 'warm up' circular walk along both banks of the River Avon - you can spot mute swans and the flash of blue kingfishers hunting for lunch under weeping willows, as colourful narrow boats chug past.

Day 3 - Shipston On Stour to Chipping Norton 14km/9mi/5hr
After a short 15 minute transfer (included) to Shipston on Stour - once an important sheep market town - you follow the Stour riverbank before ascending to rustling Whichford Wood for panoramic views to the distant Cotswolds. Enjoy lunch in Long Compton before visiting the Bronze Age Rollright Stones - an eerie stone circle by the tombs of The Whispering Knights. On arrival in Chipping Norton - 'Chippy' to the locals - visit St Mary's church, one of the richest and most ornate in Oxfordshire, located next to the remains of an ancient Norman castle!

Day 4 - Chipping Norton to Woodstock 25km/16mi/7.5hr or 17km/10mi/6hr
Follow the River Glyme to abandoned ruins of villages at Chalford, whose residents were evicted 500 years ago by Oriel College, Oxford. Criss-cross the Glyme valley before passing C18 Ditchley Park (used for wartime conferences by Churchill). You end the day walking through the pristine 2000-acre Blenheim Estate where Winston Churchill spent his childhood. We recommend you add an extra night to explore the spectacular Baroque palace fully, or visit tomorrow morning. Dine out tonight in one of Woodstock's enticing boutique restaurants.

Day 5 - Woodstock to Oxford 17km/10mi/6hr or 13km/8mi/4hr
Enjoy views of wooded Wytham Hill and the Vale of the White Horse as you leave Woodstock and pass through Bladen, last resting place of many of the Churchill family. After lunch in Yarnton, you meet the Oxford Canal, and follow narrow boats alongside the tow path into the city. Drink in the atmosphere of Oxford this evening as college students spin past on bicycles, and church bells chime across the spires.

Day 6 - Depart Oxford
Return by rail to Stratford to pick up your car (90 mins pay locally), or stay on for extra night(s) in the city.

Is this trip for you?
The walking can be either 2 boot or 1 boot - the 1 boot walk means taking taxi transfers on the morning of each walk which incurs a supplement (See Headwater’s Boot Rating System). The terrain is country paths and tracks. This will appeal to anyone with a love of varied country walking in England. Pubs, picnic spots, pretty villages, and elements of history and culture are all here.