The Cotswolds region is not only picturesque and perfect for cycling but is also full of history, offering you an unforgettable bike holiday. And intertwined within these historic trails are the famous characters that help to bring it to life.


Legendary orator, great statesman, empire builder and artist

In 1874 Winston Churchill was born into a very aristocratic family at Blenheim Palace – his grandfather’s stately home near Woodstock.

Probably most famous as one of Britain’s greatest wartime leaders, Churchill was Prime minister twice. Firstly, during the Second World War from 1940-45 and then again from 1951-55. His powerful speeches were inspirational during the war, with his immortal words ‘We shall fight them on the beaches’ said shortly before the Battle of Britain.

Churchill was a prolific writer, producing two biographies, three memoirs and a novel as well as a four-volume A History of the English Speaking Peoples. In 1953 Churchill won the Nobel Prize for Literature. Also an avid painter, Churchill used art to help combat depression and enjoyed painting impressionist landscapes.

He also had many links to the United States, not least through his American mother. Churchill was the first person to be made an honorary US citizen. In 1995 he became one of only a handful of non-Americans to have had an US Navy ship named after him.

Visit Winston Churchill’s ancestral home on your own Pedal England tour


The internationally renowned playwright who, through comedy and tragedy, has done more than anybody else to demonstrate the beauty and versatility of the English language.

Born in 1564 in Stratford-upon-Avon, Shakespeare’s father was a maker of gloves and his early life was relatively humble. At the age of 18 he married Anne Hathaway and they went on to have three children.

William Shakespeare wrote 38 plays and 154 sonnets. Perhaps his most famous are his tragedies, including Romeo and Juliet, Macbeth and Hamlet. In 1599, Shakespeare’s group of players The King’s Men worked together to build their own theatre, The Globe, on the banks of the river Thames.

In 1616 Shakespeare died and was buried at the Holy Trinity Church in his hometown of Stratford. His life and works have since been commemorated all over the world by statues and memorials.

Learn more about Stratford-Upon-Avon and how to join us on a Pedal England tour


The quiet creator, famous for her wry and wonderfully romantic characters

Born in 1775 in the rural village of Steventon, Hampshire, Austen was one of eight – six brothers and one sister.  Even as a child she was a keen writer and from an early age would produce and perform witty plays for family and friends.

She went to school in Oxford and lived in Bath as a young adult. But it wasn’t until the early 1800s, when Jane’s family moved to the village of Chawton that she started writing seriously. Her most famous work Pride and Prejudice was first published in 1813, she then went on to write other great works including Emma and Mansfield Park. In 1816 The author fell ill and died a year later. She continued to write during her illness and Persuasion and Northanger Abbey were published posthumously by her brother and sister.

Find out more about Bath.


Two special monarchs celebrated at Windsor

King Henry VIII is a formidable character in British history. Born in 1547, he went on to make sweeping changes to the country, most notably separating the Church of England from the Roman Catholic Church.

It was Henry VIII who ushered in the theory of The Divine Right of Kings which was used by future Kings and Queens as an excuse to have free reign over their subjects, as they believed it was their divine right to do so.

He is as famous for his changes to British life as he is for his personal life, Henry VIII was a gregarious, attractive and intelligent king who during his reign, had six wives. Two of which he had beheaded for not producing him a male heir to the throne.

Fast forward half a millennia and Queen Elizabeth II has a special place in many Briton’s hearts, unmatched by past Kings and Queens. She was born in 1926 and has been on the throne for 62 years, making her the longest serving monarch in history. Since taking the throne at the age of 26, she has witnessed sweeping changes of the country, seeing it go from a vast empire to an island nation.

As the holder of the British Crown, she is also the Head of State in the UK and for 15 other countries around the world. Queen Elizabeth is widely known for her dedication to her royal duties and still maintains a large number of royal engagements and commitments.

A tour of Windsor gives you the opportunity to see the grave of the great King Henry VIII, one of the Queen’s favourite homes – Windsor Castle – and soak up all the royal heritage the town has to offer.

Visit Windsor on your Pedal England tour.


From impressive roads to elegant bathing –  the empire that left its mark

In AD 43 the Romans conquered the southern part of Britain and incorporated it into the Roman Empire. Their presence would forever leave its mark on the landscape, architecture and even language of this country.

The Romans were excellent road builders and constructed military roads from clay and chalk, with these normally laid dead straight across the landscape. The Fosse and Ickneid Ways are two such roads which are still going strong and being used by walkers and cyclists today.

In approximately AD 60 the Romans built the public bathing house in Bath. A popular pastime with the Romans, this ornate spa and pump room has been enjoyed by the public for nearly 2000 years.

If you or your family love the idea of getting up close to all the heritage this region can offer and want to spend more time on cultural activities and less in the saddle, we can make that happen. Our range of packages for different ages and abilities means you can experience all the history of the area whatever your requirements.

Find the perfect tour for you

Winston Churchill, William Shakespeare, Jane Austen, Henry VIII and our ancestral architects the Romans; their inspirational achievements have helped create the country you see today. Exploring this region of England gives you a unique insight into the lives and times of the people who made this country great.