Insider's guide to Pickering

Ed Roberts 17 February 2020

Welcome to Pickering, the gateway to the North York Moors. This quaint town is a popular holiday destination for everybody that loves the great outdoors with all the activities you could ever think of getting up to on a jaunt to this part of North Yorkshire. From walking on the moors, exploring ancient castles, to cycling through forests, Pickering offers all those who come here a brilliant time. Why not stay in a self-catering holiday cottage in Pickering and discover for yourself how the locals live?


Our insider’s guide to Pickering helps you find the best places to eat and drink, learn about the town’s past and take in the most awesome beauty spots around the town.


We have fantastic holiday cottages all across the North York Moors National Park. Read our guide to discover even more places to go across the area...

The streets of Pickering

Pickering streets

If you were to go on a stroll with somebody who was born and bred in Pickering, what would they draw your attention to? Unlike a visitor, they’ve been around long enough to hear the stories, notice the mainstay details and small points of interest that the guidebooks may leave out. So, what can you find in and out of Pickering’s quirky town centre and beyond?

Take the 2-mile town walk which weaves its way past, down and around the town’s many curious edifices and outposts. Pick the Pickering Walking Trail up at the town library and you can see all the best-loved historic buildings in one fell swoop like Pickering Castle, Pickering’s three water mills, the GT Andrews designed railway station, Castle Gate, High Hall, Beach Hall, The Meeting House of Friends, The Old Cattle Market, the Market Cross, Kirk Theatre and the Beck Isle Museum. Pickering is a market town and you can pick up local fare and wares each Monday! To quote a local, the walk "takes as long as it takes." Why rush?

Conquer the castle

Pickering Castle

Pickering Castle is the town’s ancient focal point and it has a suitably interesting yet potted history. The castle ruins are at the centre of Pickering and can be seen across town as it dominates a prime hilly position.  Managed by English Heritage for a small entrance fee, you can walk around the heavily decimated walls of the 13th-century fortress. The stone castle was built for Henry II to replace a wooden motte-and-bailey fort founded by William the Conqueror. There is an on-site exhibition extolling the story of the castle’s varying fates and usages over hundreds of years. 

All aboard the North York Moors Railway 

Pickering train

One of the North of England’s most famous steam railways, the North York Moor Railway (NYMR) is an exciting prospect for those that love nothing better than stepping back in time and climbing aboard a good old-fashioned locomotive. The terminus is at Pickering so it’s an easy day out if you are staying in town; family film fans ‘keep ‘em peeled’ for Goathland Station which was used as a movie location in Harry Potter and the Philosopher’s Stone. Pickering Station has a distinctive roof structure that is actually quite magnificent. Train and architecture buffs will have seen the name GT Andrews at many Victorian stations up and down the country, Pickering’s station is a fine example of his style. Catch a train to the fascinating Cawthorn Roman Camps

Be a tree at Dalby Forest 

Dalby Forest

The locals would describe the area Dalby Forest occupies as a ‘rigg and dale’ landscape – which means a blend of ridges, plateaus and valleys. Of course, all these natural elements are embellished by the verdure and lushness of the deep forest. Explore the endless avenues and byways of the area and learn more about this beguiling park at the visitor centre. Go on a tour with rangers and check out the management’s programme of children’s and nature conservation events. You could also hire a Segway to traverse the forest with, that way you can see just as much as you may do on a bicycle or a horse. Channel your inner orangutan and swing around the treetops at the Go Ape if you have energy to burn! 

Eat like a local

Where can you get a good feed in Pickering? Well, the town doesn’t have a shortage of choice, whether you are partial to a tasty Sunday roast in a pub, the best bag of fish and chips around, or something a little more exotic like an Italian or Chinese, there’s something worth the punt.

Willowgate Bistro 


For a lovely meal out head over to the Willowgate Bistro. They regularly change up their menus and source their ingredients from named local suppliers, so you know that you are helping Pickering and North Yorkshire’s businesses to endure. Gluten-free and vegetarian and children’s menus are available too.

The Middleton Arms

Middleton Arms

This quaint pub specialises in warm welcomes, good ales and wines, and an impressive menu that would make many other gastropub owners envious.  Daily specials bolster the fine choices available; vegans and veggies are also well-considered by the chefs.

Cappleman’s Fish & Chip Restaurant


Get thee to this chippy tout suite. Fishy delights and heavenly chips await at the classic Yorkshire diner. It’s a local favourite, so don’t miss out on one of the best fish suppers to be had in the North Yorkshire area!  Also, look out for what pies and burgers are available on their creative menu.

Do the North York Moors National Park

Castle Howard

Covering a staggering 554 square miles, the North York Moors National Park (est. 1952) is huge, encompassing the Howardian Hills Area of Outstanding Natural Beauty (AONB) and Pickering is comfortably located so you’d be within driving distance of all the major points of interest. Coastal villages like Robin Hood’s Bay and Staithes (where you can go whale spotting) gild the craggy coast and are havens for wild sea birds, so twitchers take note. The park is also home to more than one Dark Skies Discovery Sites. To guard against light pollution, stargazers will definitely enjoy taking their telescope out to view the firmament in full splendour. Walk the Cleveland Way or a section of Wainwright's Coast to Coast.

Hit the empty spaces and waterways and book nature safaris or wild expeditions. At Sutton Bank National Park Centre you can see a life-changing view of the escarpment and huge valley below. Hire a bike and go! Before returning to Pickering also consider day trips to lovely Helmsley Castle, Rievaulx Abbey, Castle Howard and the gorgeous seaside town of Scarborough.

Live like a local

Stay at one of our holiday cottages in Pickering:

Railway Cottage  | Sleeps 11

Railway Cottage

Are you planning a family celebration or planning a walking holiday with friends? Then this period townhouse in the heart of Pickering is an exceptionally apt choice.  Built in 1793, many of its original features are still in situ enhancing this fab property’s allure.

We have holiday accommodation throughout Pickering and the surrounding area. Whether you have escaped the world for a romantic break or have brought the whole family to town to explore Pickering and the North York Moors National Park, we have properties large and small for you to choose from. 

View more Pickering cottages

Disclaimer: Whilst every effort has been made to ensure the accuracy of the information at the time of writing, please ensure you check carefully before making any decisions based on the contents within this article.

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