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Pickering War Weekend

Unfortunately, we can confirm that the Pickering Wartime Weekend event has been cancelled for 2020. 

However, we are looking forward to it returning next year. Read on to find out more about this fantastic event, and if you're looking for accommodation for Pickering War Weekend 2021, you can find a selection of self-catering properties at High Oaks Grange.


Over three days each October, the town of Pickering heads back to the 1940s and allows guests to experience the railway in war time.

During the event families can hop onboard steam and heritage diesel trains and relive the amazing spirit and camaraderie of World War II, whilst enjoying various war-themed entertainment and vehicle displays at stations along the iconic North Yorkshire Moors Railway line.

Each year stations along the route of the railway are transformed to create a variety of different scenarios. Past performances have included a wartime street, ‘The Sidings’, at Pickering, Home Guard demonstrations at Goathland and RAF themed Grosmont.

Other attractions in Pickering include singing, dancing, workshops, and fashion shows, in addition to living history showcases, period vehicle exhibitions and re-enactments. Many people will dress up in period costume and get involved, others prefer just to see the sights. Whilst being a fun weekend, memories of those fallen aren’t too far from thoughts as wreath laying ceremonies take place in Pickering and Grosmont.

If you're visiting Pickering for the War Weekend, where better to stay than High Oaks Grange? Our Gold Award winning self-catering properties are based just a mile from Pickering, and with a selection of luxury cottages, lodges, and glamping pods to choose from, you're sure to find the right accommodation for you.

Click here to check availability and book your stay.



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