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The best things to do in Pickering holiday cottages

The best things to do in Pickering

Emily Cunningham 16 July 2024

As well as being a convenient jumping-off spot to explore all the delights of the North York Moors National Park, Pickering is also a brilliant go-to destination in its own right. You can discover the town’s history – both ancient and modern – at the castle and local museums, sample the delicious food at a lively selection of eateries and linger in the local shops.

Travelling further afield outside Pickering has never been so much fun, either by the glorious heritage railway or under your own steam on one of the many trails. The kids will have a ball at the nearby water park and amusement park too. There’s so much to discover in Pickering you’ll never want to leave.  

Choose from a superb selection of North York Moors holiday cottages around Pickering and start planning your next memorable getaway with loved ones to this charming and historic market town.


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Pickering Castle

View of Pickering Castle through a gap in the surrounding hedge

Picture yourself as a 12th-century Norman architect eyeing the steep cliff in Pickering: ‘Perfect spot for a castle,’ you’d think, ‘that would deter marauders.’ This magnificent ruin on the edge of Pickering has witnessed numerous wars over the centuries, and even suffered from having key materials nabbed from its walls to build Scarborough Castle, but the remains are still impressive. Originally a motte and bailey structure, it was rebuilt in stone and over the years has been used as a hunting lodge, stud farm, royal holiday home, a prison and a courthouse.

Follow the footpaths around Pickering Castle to see how effective the setting would have been to protect the castle, then make your way to the top to be rewarded with a superb vista of the North Yorkshire Moors.

Good to know

  • Location: Castlegate, Pickering YO18 7AX
  • Opening times: 10am–5pm every day in summer, check website for details
  • Entry fee: Adults £10.50, children £5.50 (15% discount if bought online in advance)
  • Parking: There’s a free car park at Pickering Castle
  • Stay nearby: Isabella Cottage | sleeps 3

Pickering walks

A visit to Pickering gives you spectacular scenery on your doorstep and what better way to explore it than lacing up your walking boots and setting off on foot? 

Levisham to Pickering

NYMR steam train heading through moorland between Levisham and Pickering

We love combining a walk with a jaunt on the steam train to Levisham – it’s so cheering to have the train puffing past as you amble eight miles home, mercifully nearly all downhill, following the railway tracks before joining the path by the side of Pickering Beck (stream) for the last stretch. 

Good to know

  • Starting point: Levisham Station , Pickering YO18 7NN
  • Distance: 8 miles
  • Difficulty: Easy
  • Stay nearby: Standfield Hall Cottage | sleeps 4 

Castle Howard circular

Close up of the Great Lake at Castle Howard with the stately home in the background

The beautiful grounds of Castle Howard provide the location for a wonderful circular walk through Yorkshire’s Howardian Hills. It’s also an opportunity to glimpse this stunning castle for free. You’ll pass through the charming village of Coneysthorpe before being greeted by the photo-friendly view of the castle across the Great Lake. A meander through meadows and woodland, spotting the castle’s follies and temples as you go, takes you back to the car park where you began.

Good to know

  • Starting point: Castle Howard car park, York YO60 7DA  
  • Distance: 5 miles
  • Difficulty: Easy
  • Stay nearby: Cherry Tree Lodge - Welburn | sleeps 4 

The Hole of Horcum

Green fields sloping down to the Hole of Horcum in the North York Moors

Yorkshire is crammed full of myths and legends about its landscape, and the Hole of Horcum is one such example. This incredible geographical feature – a bowl-shaped valley – is also known as ‘the devil’s punchbowl’ and was thought to be created by Wade the Giant grabbing a handful of earth to throw at his wife. A lovely 5-mile stomp gives you views of Newtondale, Skelton Tower and the Vale of Pickering.

Good to know:

  • Starting point: Saltergate car park, Pickering YO18 7NR
  • Distance: 5 miles
  • Difficulty: Moderate
  • Stay nearby: Lock Cottage | sleeps 6

Pickering Shopping

View down Pickering high street with a selection of shops and cafes

Among the quirky selection of independent shops there are signs of Pickering’s farming heritage, with gun shops and gentlemen’s outfitters next to more conventional stores to browse in. It’s easy to while away many an hour in The Pickering Book Tree, a charming bookshop offering a personalised service from its bookworm staff. There are lots of author events throughout the year too so keep an eye on the calendar when you visit.

One of the pleasures of going on holiday is sampling the local produce, and where better to source it than a farm shop? Just outside Pickering, Cedarbarn Farm Shop sells fresh vegetables and meat from its own farm as well as a wealth of other goodies from nearby producers. There’s also an exceptional café and dog field you can book to give your pooch a walk.

A sweet treat makes a great present to remember Pickering by, so head to Birdgate Chocolatiers in the town centre for dreamy chocolates. The Yorkshire Moors Baa, a bar filled with heather honey ganache and ‘droppings’ (raisins), makes a memorable gift. 

Don’t miss

  • Browsing the stalls at Pickering market which is held in the town every Monday
  • Visiting the Hidden Market and finding everything from jewellery to furniture within the quirky indoor market
  • Weighing out exactly what you need with zero waste and excess packaging at The Old Weigh

Pickering pubs

Red wine being poured into glasses

A short stroll from Pickering town centre, The Sun Inn is a rustic delight. There’s an enormous beer garden, local ales including Hair of the Dog by the Pennine Brewing Company and family-friendly activities. What you won’t find are TVs, fruit machines or Wi-Fi – it’s a chance to remember life before screens. 

A pair of swans inhabit Pickering, both jockeying for position of best pub grub in town – The White Swan in the market place offers gorgeous meals for a special night out – check out the impressive cheese board of British cheeses. Meanwhile The Black Swan on Birdgate is famous for its Sunday roasts, with succulent beef reared in the county. Which to choose? Why not go to both if you’re staying for a few days? 

Our favourites


Pickering restaurants

Traditional buildings in the centre of Pickering in front of the town church

Attention to detail is key to dining in Pickering: the husband-and-wife team of the small but perfectly formed Willowgate Bistro work hard to provide the perfect restaurant experience, with carefully cooked meals, vegetarian and gluten-free menus (instead of just the odd veggie or GF option) and early sittings for families with children.

For a step back in time, make the trip to nearby Middleton Post Office and Tea Parlour. (You won’t be distracted by stamps and passport applications as the tea parlour is behind the post office.) Tuck into a glorious afternoon tea consisting of sandwiches cut from locally made bread and homemade cakes, all served on vintage china. 

For a stonking fish-and-chip supper, swing by Cappleman’s, there’s a small dining area along with the traditional takeaway service, perfect for rainy days (and dog-friendly too). As well as top-notch cod, why not try the succulent Whitby scampi, black pudding fritters and mushy pea bombs?

Our favourites


Beck Isle Museum

Blacksmiths at work at Beck Isle MuseumImage credit: Beck Isle Museum

An elegant Grade II-listed mansion is the home of Beck Isle Museum, which boasts an impressive display of local artefacts that illustrate the social history of Ryedale. The warren of interconnected rooms showcase different aspects of 18th- and 19th-century life, including a tailors, hairdressers and pharmacy. Check out the vintage ‘Rocket Type’ washing machine and self-propelling chair, a forerunner to the modern wheelchair.

Dogs on a lead are welcome throughout, and while there isn’t a café, you’re encouraged to borrow one of their picnic blankets for lunch by the beck (stream) in the grounds of the house.

Good to know

  • Location: Bridge Street, Pickering YO18 8DU
  • Opening times: Monday–Thursday and Saturday from 10am–4pm (25 March2 November)
  • Entry fee: Adults, £8, children, £4, under-fives, free 
  • Parking: Free but parking is limited outside the museum
  • Stay nearby: Pantile Cottage | sleeps 3 + 2 dogs

North Yorkshire Moors Railway

Close up of an NYMR steam train travelling through the moors

An uplifting day trip and wonderful way to explore 24 miles of the beautiful Yorkshire Moors is via the North Yorkshire Moors Railway (NYMR), on board one of its steam or heritage diesel trains. Happily, if you’re visiting Pickering, this station is one of the most picturesque, with 1930s décor throughout and a traditional tearoom housed in a beautiful Victorian building. 

Each of the six stations on the line has its own charm, in particular Goathland, which was used in both the first Harry Potter film and episodes of Heartbeat. Levisham is home to the NYMR’s artist in residence while Grosmont Station is where the locomotives are maintained and restored. Step through the George Stephenson tunnel to the shed shop for a glimpse of steam engineers hard at work.

Good to know

  • Location: Pickering Station, 12 Park St, Pickering YO18 7AJ
  • Opening times: See the website for timetables
  • Ticket prices: To travel one stop from Pickering to Levisham, adults £13.50, under-15s go free   
  • Parking: £5 all day
  • Stay nearby: Railway Cottage | sleeps 11

Flamingo Land

Close up of a red and yellow rollercoaster

Combining an amusement park with a zoo means that Flamingo Land really has something to offer the whole family. The nine white-knuckle rides include the intriguingly named ‘Sik’ rollercoaster that has 10 inversions while the seven gentler rides are perfect for younger children.

As the park covers a lot of ground, you’ll be grateful for the three types of transport that travel between attractions – the land train, people-mover and monorail. They’re lots of fun in their own right and the monorail gives a great view of the baboon enclosure and cheeky meerkats from your elevated position above the treetops.

The zoo is a great opportunity to see exotic beasts up close, including lions, tigers and hippos. There are also more obscure creatures such as gila monsters and tenrecs to satisfy the naturalists among you.

Good to know

  • Location: Off the A169, Kirby Misperton, Malton YO17 6UX
  • Opening times: 10am–5pm on weekdays and 10am–6pm on weekends
  • Entry fee: Visit the website for details
  • Parking: Free parking
  • Stay nearby: Dove Cottage | sleeps 4 + 2 dogs

Eden Camp Modern History Museum

Watch tower, tank, spitfire and 1940s mannequins at the front of Eden Camp MuseumImage credit: Eden Camp Modern History Museum

Bringing history alive in vivid sight, sound and smell, Eden Camp Modern History Museum is a recreation of what it was like living through World War 2. A former prisoner of war camp has been transformed into 22 themed huts staffed by costumed guides, each with a family-friendly activity to get involved with. Over the summer holidays there are special workshops to try, including building a peg plane, making tack biscuits and creating a tank out of egg boxes.  

To immerse themselves in the wartime experience, kids will love the Eden Camp Ration Pack in the café, plus the Prisoner of War Exercise Compound is a fabulous adventure playground. No need to leave your dog at home – they’re welcome throughout and there’s even a pup-friendly section of the café.

Good to know

  • Location: Off the A169/A64 junction, Malton YO17 6RT
  • Opening times: 10am–5pm every day until 2 November
  • Entry fee: Adults £15, children aged five–16 £13, under–fives are free
  • Parking: Free parking
  • Stay nearby: Waterlily Lodge | sleeps 4 + 2 dogs

North Yorkshire Water Park

Couple in a kayak on the water

Whether it’s on, in or by the water, North Yorkshire Water Park offers every sort of splashy fun imaginable. Older children and the young at heart will love the aquapark, a floating inflatable obstacle course, and there’s a mini version perfect for youngsters. You can also try your hand at paddleboarding, wakeboarding and kayaking under the expert guidance of trained instructors. Keep warm in the water in a wetsuit, available to hire for £5.

If you’d prefer to stay dry, whizz over the lake on the 250-metre-long zipline or check out the Adventure Wood Activity area, with axe-throwing, archery, low ropes and bush craft. Don’t forget to round off the day at the café, which sells hearty burgers, pizzas and nachos.

Good to know

  • Location: Long Causeway Rd, Wykeham, Scarborough YO13 9RA
  • Opening times: 8am–8pm from May to September
  • Entry fee: See the website for details
  • Parking: Free parking
  • Stay nearby: Church Beck House  | sleeps 8

Map of things to do in Pickering

Find the best places to go and things to do around Pickering with this handy map. 

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Stay at a holiday cottage in Pickering

Hot tub in the garden at Blacksmiths Cottage near Pickering

Blacksmiths Cottage | Sleeps 2 + 1 dog

Pickering is so well-placed to explore all that North Yorkshire has to offer. You can choose from a romantic cottage in the heart of the town if you want the shops and eateries close to home, or ‘head for the hills’ for a dog-friendly Pickering retreat with acres of countryside on your doorstep.   

Choose from a superb selection of North York Moors holiday cottages around Pickering and start planning your next memorable getaway with loved ones.


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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