Day Trip to Pickering from Cliff House Holiday Cottages

Just a short drive from Cliff House Holiday Cottages, Pickering is our nearest market town and a wonderful place for a day out. With steam trains, medieval churches, a motte and bailey castle, fascinating museums and even its own independent bookshop, there’s something for everyone. Here’s our guide to the best things to do in Pickering.

Steam Trains at Pickering Station

We started our day at Pickering Station, home of the North Yorkshire Moors Railway. Watching the 09:00 steam train depart is always a highlight, with the sound of the locomotive echoing as it begins its journey across the North York Moors.

The station museum is a must-see too, with plenty of railway history and curiosities for all ages. It’s one of the top Pickering attractions for families and train enthusiasts alike.

Market Place and the Pickering Wall Paintings

From the station, we walked up through Market Place, lined with independent shops and cafés. At the top sits the Church of St Peter and St Paul, home to the famous Pickering Wall Paintings.

Believed to date from the 1450s, these medieval murals were whitewashed, rediscovered in 1852, covered over again, and finally revealed once more in 1876. Today they are regarded as some of the most important surviving medieval wall paintings in England.If you’re interested in medieval churches in North Yorkshire, this is an unmissable stop.

If you’re interested in medieval churches in North Yorkshire, this is an unmissable stop.

Exploring Pickering Castle

A short walk brings you to Pickering Castle, a classic motte and bailey castle in Yorkshire built under William the Conqueror. The remains of the keep and curtain walls give a real sense of its defensive past, while the views across the Vale of Pickering from the top are worth the climb.

Beck Isle Museum

Back in the town centre, the Beck Isle Museum is a gem. Run entirely by volunteers, this social history museum is packed with exhibits. Highlights include a reconstructed bar, a working blacksmith’s forge, an old printing press, and paintings by Rex Whistler created in 1943 for a children’s party in Pickering.

For those interested in the stories of everyday Yorkshire life, the Beck Isle is one of the best Pickering attractions.

Independent Shops and Local Pubs

No day out in Pickering would be complete without a browse through The Pickering Book Tree, the town’s welcoming independent bookshop. It’s a great place to pick up a holiday read or a gift to take home.

We rounded off our visit with a pint at The Black Swan, where the beer is brewed by the owners themselves — a fitting end to a day spent exploring. If you’re looking for traditional pubs in Pickering, this one is well worth a stop.

Planning Your Day Trip to Pickering

Pickering is the perfect base for exploring the North York Moors National Park and makes for a rewarding day trip from our holiday cottages near Pickering. With its steam trains, medieval art, Norman castle and independent shops, the town combines history and character with plenty to do for all ages.

When you stay at Cliff House Holiday Cottages, you’ll find Pickering and the wider North York Moors right on your doorstep — ready to explore at your own pace.