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The best things to do in Helmsley holiday cottages

The best things to do in Helmsley

Julie 29 January 2024

With cobbled streets that are filled with honey-hued buildings and a stream running along the back of the market square, Helmsley is a handsome North York Moors town that makes an ideal base for a short break or longer holiday.

From adventures in an ancient castle to wandering around a walled garden, there are lots of things to do in Helmsley with plenty of pretty countryside to explore in all directions. Take a look at some of our favourite Helmsley activities and start planning your next getaway to the North York Moors National Park


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Have a dog-friendly day out at Helmsley Castle

Helmsley Castle with sheep grazing in the foreground

Visiting the remains of Helmsley Castle, perched high on a hill above the town, is one of the best dog-friendly things to do in Helmsley with huge grounds that are just right for adventures with four-legged friends. Information boards are dotted around the ruined remains to show how the various rooms of Helmsley Castle once looked, with a free audio tour to help you explore the extensive site.

Don’t miss

  • Bronzed archers in the grounds are ready for battle to remind you of Helmsley Castle’s past as an important medieval fortress. Today they stand guard over visitors picnicking in the grounds.
  • Head inside the original medieval castle walls to find a separate building that was once a grand Tudor mansion and now houses a fascinating museum with various artefacts and hands-on exhibits.
  • There is a shop and visitor centre at the entrance to Helmsley Castle where you can pick up souvenirs, guide books and various lovely English Heritage gifts including biscuits and blankets.

Wander around Helmsley Walled Garden

Flower-lined pathway at Helmsley Walled Garden

Just down the hill from Helmsley Castle is the historic and dog-friendly Helmsley Walled Garden, a serene space that dates back to the 18th century when it grew produce for the nearby Dunscombe Estate. More recently Helmsley Walled Garden was featured in The Secret Garden film and has an emphasis on therapeutic horticulture to improve visitor’s mental wellbeing.   

Don’t miss

  • Wander through the various sections of Helmsley Walled Garden which include colourful borders filled with irises, peonies and vibrant flowers and serene spaces such as The White Garden and The Garden of Contemplation.
  • Grab food to feed the friendly chickens that wander freely around the wildlife-rich pond before heading to an orchard that contains more than 100 varieties of apple tree.
  • Head to The Vinehouse Cafe where dogs will be made very welcome as you tuck into homemade cake and dishes made from produce that’s grown in the gardens. The cafe also comes with wonderful views of Helmsley Castle.

Splash around at the Helmsley Open Air Swimming Pool

Woman swimming underwater with goggles and cap

Helmsley has its own outdoor swimming pool which is open seasonally for anyone who fancies an al fresco dip. Helmsley Open Air Swimming Pool is 25 metres long so perfect both for serious swimmers and family fun. It’s typically heated so the water will be lovely and warm but you can also try cold water swimming in a ‘Cool Pool Swim’ session in September.    

Don’t miss  

  • Fun sessions are perfect for families with inflatables and toys available in the pool for kids to play with. Open sessions are great if you are looking for a proper swim and lane-only swims are available on Thursday evenings in the summer. 
  • There’s a snack bar where you can get refreshments following your swim with picnic tables that look out over the surrounding North York Moors countryside and a nearby play area with a zip wire for little ones.
  • Sessions including yoga and aquafit are also available at Helmsley Open Air Swimming Pool, as well as special opportunities to take a magical twilight swim during summer solstice or under the full moon.    

Sit down to a peaceful picnic at Rievaulx Abbey

Rievaulx Abbey on a clear summer's day

A few miles from Helmsley are the beautiful remains of Rievaulx Abbey, a Cistercian monastery dating back to 1130 that is hidden in a deep valley near the River Wye and was once one of England’s great abbeys. 

We think a visit to Rievaulx Abbey is a wonderfully romantic thing to do, especially as you can stroll hand in hand through the gorgeous grounds before settling down for a peaceful picnic for two with goodies from the nearby Auntie Anne’s Castlegate Bakery in Helmsley.

Don’t miss

  • Getting your sketchbook or easel out to draw or paint Rievaulx Abbey, the site was a popular subject for artists during the Romantic Period in the early 19th century. 
  • Visiting the on-site museum where you’ll find precious objects such as gold coins and elaborate carvings. There’s also lots of information on the history of Rievaulx Abbey and changing exhibitions throughout the year.
  • Follow in the footsteps of medieval monks by taking a scenic 3-mile walk through peaceful woodland and rural fields from Helmsley Castle to Rievaulx Abbey. 

Visit a pair of National Trust sites

Nunnington Hall with flower filled gardens in the foreground

Just up the hill from Rievaulx Abbey is Rievaulx Terrace, a landscaped pleasure garden with woodland walks, abbey views and plenty of space for kids and four-legged friends to run around and let off steam. Take a short drive from here to Nunnington Hall, a Yorkshire manor house on the banks of the River Rye, for a family-friendly day out in the North York Moors.

Don’t miss

  • Seeking out a pair of stunning 18th-century temples at Rievaulx Abbey then head into the woods to build a den in the wild play area. You can enter inside the Ionic Temple to see ceiling frescoes, painted by Italian artist Giuseppe Mattia Borgnis. 
  • Heading to the attic of Nunnington Hall to discover one of the world’s finest collections of miniature rooms. There are also various exhibitions throughout the year and the chance for kids to dress up in period costume.
  • The gorgeous gardens at Nunnington Hall are fully organic and include spring meadows, vibrant flower borders, secret spaces and a collection of colourful peacocks.   

Tuck into a tasty meal at a Helmsley tea room or restaurant

Exterior of Mannion and Co in Helmsley

Whether you fancy a casual lunch with friends or tucking into a tasting menu during a date night, Helmsley has got you covered. There are plenty of places to eat in and around the North York Moors market town from charming tea rooms to fine dining restaurants.

Don’t miss

  • Located just outside of Helmsley in the small village of Scawton, The Hare serves a nine-course tasting menu in the characterful surrounds of a 12th-century inn complete with wooden beams and exposed brickwork.
  • Just across from Helmsley Castle is Mannion & Co, a daytime eatery where you can get brunch options such as eggs benedict with charcuterie platters for lunch and champagne by the glass to wash it all down.
  • There are lots of tea rooms dotted around Helmsley including The Cocoa Tree which is dog friendly and the Feather Trail Cafe where you can get delicious homemade cakes and scones.  

Take a Hawk Hike at the Duncombe Park Estate

Hawk sitting on a handler's glove

Duncombe Park, which is privately owned by the Duncombe family, is a grand stately home on the edge of Helmsley that’s surrounded by around 450 acres of parkland and gardens. Although the house itself is typically closed to the public, there are regular events in the grounds along with woodland walks and a large nature reserve.

Don’t miss

  • The National Centre for Bird of Prey is based at Duncombe Park and open every day from early February to early November. There are regular flying demonstrations with the different species of birds and hawk, owl and raptor experiences also available.
  • You can wander around follies, sculptures, flower beds and a scented ‘Secret Garden’ (Duncombe Park featured as Misselthwaite Manor in the 2020 film) when the formal gardens are opened to the public between April and August each year.
  • The Duncombe Park Steam Rally is a popular Yorkshire event which takes place each July in the grounds with vintage cars, steam engines and a fun fair with weekend camping available.

Follow the Cleveland Way to Sutton Bank

Signpost for Cleveland Way with wooden gate and country path

The Cleveland Way is one of England’s original National Trails and the long-distance footpath runs all the way from Helmsley in the North York Moors to Filey on the Yorkshire Coast. The first part of the route starts at Helmsley Castle, where a stone sculpture with an acorn marks the start of the trail, and takes you to the Sutton Bank National Park Centre.

Don’t miss

  • The view from Sutton Bank over the Vale of York and the glacial Gormire Lake is spectacular. In fact it’s so good it was named ‘England’s Finest View' by famed Yorkshire vet James Herriot.
  • Sutton Bank National Park Centre is a Dark Sky Discovery Site with a Star Hub where you can enjoy special stargazing experiences throughout the year. The Milky Way can regularly be seen and the Northern Lights have been spotted from Sutton Bank.
  • There’s a cafe, information centre and play area at Sutton Bank so lots to keep the whole family happy. It’s also worth taking a slight detour to The Kilburn White Horse, a 97-metre figure that was cut into the hillside during the 19th century.       

Hit the Helmsley shops

Street in Helmsley with shops and tea rooms

Helmsley is a bustling market town that’s filled with independent food stores, classic country stores and family-run shops that are full of quirky gifts. If you fancy spending time shopping in Helmsley, you’ll find upmarket chains such as Fairfax & Favor along with ladies' boutiques like Pennita where you’ll want to take your time browsing the lovely things on offer.

Don’t miss

  • Hunters of Helmsley is a delicatessen that sells artisan food and drinks from a range of local suppliers with pies, pasties and cakes for a delicious Yorkshire picnic. There’s also the Helmsley Traditional Sweet Shop with old-fashioned jars of humbugs and bonbons.  
  • Browns is an independent family-owned department store with branches in York and Helmsley that’s worth visiting while Holme Lea Interiors has lots of cushions, throws and accessories for creating a country cottage look.
  • The Saltbox Gallery has a constantly changing collection of contemporary art, sculpture and ceramics for sale. Agnus & Co and Patridge & Teal are both Helmsley gift shops selling scarves, soaps, candles, jewellery and homeware. 

Sup a pint at a Helmsley pub

Sign for Summat's brewing at Helmsley Brewing Co

There are lots of Helmsley pubs to call in for refreshments, whether you fancy supping on a pint of real ale with a four-legged friend by your side or getting some cocktails with the girls. The Helmsley Brewing Company produces handcrafted ales and bitters in the town with names such as Howardian Gold and Yorkshire Legend and there are plenty of classic country inns where you can wash down a hearty lunch with a drink or two. 

Don’t miss

  • The brew tap at Helmsley Brewing Company called Summat’s Brewing is where you can sample their fresh draught and bottled beers. Head upstairs to Angel’s Share, a speakeasy-style bar with lots of cocktails to try. 
  • The Feathers and The Royal Oak are both dog-friendly Helmsley pubs located on the marketplace with open fires, cosy bars and home-cooked food on the menu.
  • The Black Swan at Helmsley dates back to the 15th century and part of the original black-and-white timbered Tudor exterior still remains. Head inside for classic British pub food, a well-stocked wine cellar and signature serves of gin.    

Bid at the Yorkshire Auction House in Kirkbymoorside

Auctioneer with gavel raised

Around 6 miles from Helmsley is Kirkbymoorside, a Ryedale market town on the southern edge of the North York Moors that’s filled with antique shops, art galleries and workshops. You can also bid on anything from toys to militaria at Ryedale Auctioneers, which is helmed by Angus Ashworth and featured on The Yorkshire Auction House TV series.

Don’t miss

  • Towler’s Chemists in Kirkbymoorside which was originally a 19th-century coaching inn called The Green Dragon and still retains a licence to sell alcohol. There’s a well-stocked wine cellar at the shop and experts on hand to help you choose your tipple.
  • Ryedale Open Studios is run each September in conjunction with the Vault Art Centre in Kirkbymoorside and is the chance to see various local artists and makers at work.
  • Teeing off at Kirkbymoorside Golf Club where you can play a round of golf surrounded by beautiful North Yorkshire countryside. Visitors are welcome at the club and there’s an on-site restaurant serving everything from cakes and light bites to a Sunday carvery.  

Browse the stalls at a Yorkshire market

Selection of baked goods on stall at Malton market

Helmsley market has a rich history dating back to 1191 and every Friday you can browse a selection of stalls around the cobbled town square and medieval market cross. There’s always a bustling atmosphere on market day in Helmsley with everything from fresh Yorkshire meat and vegetables to homemade jewellery and crafts available to buy from the various local traders. 

Don’t miss

  • There’s also an artisan food market which takes place in Helmsley Town Hall on the third Friday of every month where you can buy Yorkshire meat directly from the farmers along with artisan cheese and chocolates.
  • Just down the road from Helmsley is the pretty village of Hovingham where there’s a market on the first Saturday of each month. You’ll find more than 60 stalls in and around the village hall at this market run by local volunteers.
  • Other shopping events held in and around Helmsley include regular craft fairs at  Helmsley Arts Centre and a Wednesday market in Kirkbymoorside. A little further away in Malton is the Malton Monthly Food Market on the second Saturday of each month.   

Plan your Helmsley getaway

Aerial view over Helmsley with Castle in the foreground

If you have been inspired to visit Helmsley and try some of these things for yourself, you’ll find a range of holiday cottages in and around the North York Moors town.

Whether you’re looking for a dog-friendly getaway to the countryside or somewhere for the family close to the centre of town, browse our range of Helmsley cottages to find your perfect base for adventures. 



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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