Pickering's 1940s Weekend is back!

A Celebration of the 1940s

This October the charming market town of Pickering will transform into a living snapshot of the 1940s for the first time in six years. For one unforgettable weekend, the streets come alive with vintage vehicles, music, dancing, and re-enactments that celebrate Britain’s wartime spirit. Last taking place in 2019, War Weekend was one of North Yorkshire’s most popular events, drawing thousands of visitors who come to experience a unique step back in time.

This year the first returning 1940s Weekend will take place from Friday 10th to Sunday 12th October 2025. Expect to see classic cars and military vehicles, street entertainment, parades, and authentic wartime displays. Many visitors love to dress up in period costume, adding to the nostalgic atmosphere that fills the town.

What to Expect

From swing music echoing through the streets to vintage market stalls selling everything from uniforms to ration books, there’s something for everyone to enjoy. The event also includes:

Live music and dancing in the town square
Re-enactments and military parades
Themed food and drink stalls
Displays at Pickering Station, run by the North Yorkshire Moors Railway

The railway itself often joins in the celebrations, with staff dressed in period uniforms and steam trains adding an authentic backdrop to the festivities.

Stay Nearby at High Oaks Grange

If you’re joining the celebrations, High Oaks Grange is the perfect base — just two miles from Pickering. After a day soaking up the sights and sounds of the 1940s, you can return to your luxury lodge, cottage, or glamping pod and relax in peaceful surroundings.

Many of our guests love to combine the War Weekend with a few extra days exploring the North York Moors, Dalby Forest, or the nearby coastal towns of Whitby and Scarborough.