Churchill Trail Revealed For Isle Of Wight %7C Group Travel News %7C Ventor%2C Isle of Wight

The Isle of Wight has launched a new Churchill Trail to help guide visitors around the area also known as Winston’s Island.

The trail gives visitors an insight into Winston Churchill’s time  on the island, as well as his ancestors and descendants’ links with the island.

The trail begins at Cowes, which is where Winston’s parents first met and became engaged.

The story goes that in 1873, Lord Randolph Churchill was rowed to the Cowes Week guardship HMS Ariadne and spotted American Jennie Jermone dancing. He fell in love instantly, and by the third day had proposed during a walk in the garden at the rented Rosetta Cottage.

The trail then goes on to Osborne House where Winston once swam with Queen Victoria’s grandsons, and concludes at Carisbrooke, where Winston’s relation, Earl Spencer, was held prisoner in the castle.

Other stops include Ventor, where Winston spent four holidays with his brother and nanny, Yarmouth, where his descendant John Churchill was made MP, and Compton Beach, where he built sandcastles on the dinosaur sands.

Churchill spent many holidays in Ventor and, when asked during World War Two about his first memories, replied; “I love Ventor.”

The Churchill Trail was inspired by research that has also featured in a recent book by Anthony Churchill, which highlights the links between the family and the island. 

The trail was created to highlight the Churchill family’s varied connections with the Isle of Wight, from the 17th century through to the present day.

The route can be followed by car, bike, or foot and includes 12 different locations around the island.

The Churchill Trail is now available at and is also available at The Isle of Wight Visitor Information Centre and tourist information points around the island.