Ten things to do in Helmsley holiday cottages

Ten things to do in Helmsley

Julie Smith 08 March 2021

As the only market town that’s fully within the boundaries of the North York Moors National Park, Helmsley makes an ideal base for exploring this beautiful part of the UK. Not only is Helmsley surrounded by the heather-clad moorland that the North York Moors are famous for but it’s also just a short drive away from the National Park’s glorious heritage coastline.

With a 900-year-old castle to explore, a beautiful walled garden to walk around and a range of excellent shops and eateries to call into, there are lots of reasons to pay a visit to this North York Moors market town. We have compiled ten of our favourite things to do in Helmsley, hopefully giving you lots of inspiration for your next short break or holiday to Yorkshire. 

Skip to:

👉 Helmsley Castle

👉 Rievaulx Terrace

👉 Afternoon tea

👉 Helmsley shopping

👉 Helmsley Walled Garden

👉 Cleveland Way walks

👉 Helmsley food and drinks

👉 Helmsley Open Air Pool

👉 Duncombe Park

👉 Dog-friendly Helmsley pubs

1. Explore Helmsley Castle

Helmsley things to do

The remains of this 900-year-old fortress keep watch over Helmsley from an elevated spot above the market town. 

A museum tells the story of Helmsley Castle’s history and there are large gardens and dog-friendly grounds to explore with picnic areas where you can sit and make the most of wonderful views over the town. You can wander around the extensive ruins with several intact rooms and an array of informative displays to explore.

Entrance to the English Heritage site is through a lovely gift shop where you can get everything from strawberry wine and mead to souvenirs of your visit.

2. Admire the view from Rievaulx Terrace

Rievaulx Terrace

A scenic 3-mile walk from Helmsley Castle are the extensive ruins of Rievaulx Abbey, another English Heritage site that was once one of the country’s most eminent Cistercian monasteries. The pretty ruins are perfect for a family game of hide and seek but the best way to take in the true scale of them is from the National Trust’s Rievaulx Terrace which looks out over the site.

The 18th-century landscaped gardens of Rievaulx Terrace sit alongside natural woodland and include temples with intricately painted ceilings, wildflower meadows and lush green lawns where you can spread out a rug in the summer months.

Along with the spectacular views, other highlights of Rievaulx Terrace include giant outdoor Jenga and chess sets, a sculpture trail to follow and a natural play area with wooden carvings, cloud viewers and stepping stones.

3. Tuck into a traditional afternoon tea 

Things to do in Helmsley

Like many market towns and villages in the North York Moors, Helmsley has a selection of charming tea rooms where you can enjoy home-made cakes and dainty sandwiches washed down with a cup of Yorkshire tea. 

One of my favourite places for afternoon tea in Helmsley is the Black Swan, a wonderfully characterful building that dates back to the 15th century. During the summer months, you can take afternoon tea in the Black Swan’s pretty walled garden while, in the winter, the cosy tea room with various nooks and crannies is warmed by an open fire. The afternoon tea is served on a tiered silver tea stand and can be washed down with a choice of 27 different teas and an additional glass of bubbly for an extra-special treat.

Other great choices for afternoon tea in Helmsley are:

  • The Cocoa Tree
  • Mannion and Co
  • Castlegate Tearoom

4. Mooch around the market square

Helmsley market squareImage credit: Jack Cousin


Helmsley has a long history as a market town; it was first granted the status by Robert de Ros in the 12th century. The market originally took place in Helmsley’s ancient churchyard but was moved, along with the original market cross, to the town square in 1467. Helmsley was granted market town status in the 12th century and a market is typically held in Helmsley’s historic square each Friday. 

In addition to the main Helmsley market, there are several other monthly events:

  • Regular Friday craft fairs take place in the Old Town Hall with stalls selling knitted baby clothes, handmade cards and a range of locally crafted giftware.
  • Monthly food markets celebrate the best North York Moors producers with locally reared meats, a range of Yorkshire cheeses, and artisan gins and chocolates.
  • A short drive from Helmsley is the small village of Hovingham where there is a market on the first Saturday of every month with over 60 stalls of local produce.

The cobbled streets and courtyards around the market square are also home to a range of independent shops:

  • Twig and Twine is a florist that also sells vintage pieces and items for your home alongside the beautiful fresh flowers.
  • Browns is a family-owned department store where you can pick up premium skincare and beauty products, and the latest ladies fashions.
  • Tucked away in a quiet courtyard with a giant wooden bear outside, The Ginger Bear is the place to go for gorgeous gifts, especially if you are looking for something quirky or a little bit different.
  • Visit the Crafty Pair on the high street in Helmsley for homemade needle-felted pieces and range of craft supplies. There are also regular workshops where you can learn the various needlework techniques.
  • Buy classic British sweets straight from the jar at Helmsley Traditional Sweet Shop.
  • Pick up handcrafted hats for a special occasion at Amanda Field Couture Millinery or designer watches and quality pieces at Libby Butler Jewellers.

Helmsley is one of the most dog-friendly places around and well behaved four-legged friends are very welcome in most of the market town’s independent shops. 

5. See some beautiful blooms at Helmsley Walled Garden

Things to do Helmsley

This wonderful walled garden at the foot of Helmsley Castle dates back to the 18th century when it was used to grow fruit and vegetables for the nearby Duncombe Estate. After being carefully brought back to life during the 1990s, it is now one of Yorkshire’s most glorious gardens - even featuring in the 2020 adaptation of The Secret Garden.

The dog-friendly Helmsley Walled Garden is divided into a number of different borders and plant collections which range from bright and colourful floral displays to peaceful horticultural spaces. Highlights of the garden include:

  • The hot border which flowers from early June with a collection of vibrant purple, red and orange blooms.
  • The tranquil white garden, containing a number of different shapes and sizes of flower which are all in the same colour palette of green and white and are surrounded by pretty wildflower meadows.
  • The long border, featuring springtime blossoms and fruit trees growing alongside a footpath which will take you through the garden.

After spending time enjoying the Helmsley Walled Garden, we recommend heading to the on-site cafe which is set in one of the original Victorian vine houses with an outdoor courtyard for al fresco dining. The Vine House Cafe is fully licensed too so you can enjoy a fabulous gin cocktail to wash down your tasty lunch.  

6. Walk along the Cleveland Way 

Things to do in Helmsley

The Cleveland Way is one of the UK’s National Trails and walking along this waymarked route is a perfect way to explore the North York Moors countryside that surrounds the market town of Helmsley. 

The route covers 109 miles in total and the starting point for walking the Cleveland Way is an acorn sculpture in the Helmsley Castle Car Park. The first 3 miles of the walk will take you to nearby Rievaulx Abbey where you can either circle back to Helmsley or carry on to Sutton Bank which is an additional 4 miles each way.

The view from Sutton Bank, which looks out over the tranquil Gormire Lake, was described by James Herriot as the finest view in England so it’s well worth lingering here and soaking in the mesmerising North York Moors scenery. The Cleveland Way will eventually take you across to the coastline and to towns and villages like Whitby, Staithes, Robin Hood's Bay and finally Filey but that’s probably for another day...

Other great Helmsley walks to try include:

  • A 6.5-mile circular walk which follows the meandering path of a gently babbling brook. 
  • A 4-mile circular walk around Helmsley which takes you along the banks of the River Rye and across peaceful farmland with far-reaching views of the countryside.
  • Through the Beck Dale woodland on the edge of Helmsley.
  • An 8-mile circular walk which takes in both the Riccal Dale and Monk Holme woods following bridleways and footbridges with several climbs to tackle along the way. 

7. Enjoy some tasty local food and drink

Things to do in Helmsley

There’s no shortage of food options to enjoy during a short break or holiday to Helmsley, with a wide array of eateries around the market town covering everything from bistro dining to delis where you can pick up some top-notch local food and drink.

  • There are a couple of classic fish and shops, Deep Blue and Laucia Fisheries, where you can get freshly fried cod or haddock to eat in or take away.  
  • For something a little fancier, the Star Inn at Harome serves Michelin-starred food in a characterful thatched 14th-century inn at the edge of the town.
  • The Hare at Scawton is another great fine-dining option on the edge of Helmsley. The restaurant holds three AA rosettes and serves a regularly changing tasting menu.
  • If you are in the mood for al fresco dining, you can pick up a range of fresh supplies at Hunters of Helmsley for an idyllic summer picnic by the stream that runs along the side of the cobbled town.
  • For fine wines and locally produced drinks, head to Helmsley Wines or the Helmsley Brewing Company.
  • If you’re holidaying with a four-legged friend, La Trattoria is a dog-friendly Italian restaurant serving freshly made pizza, pasta and antipasti.

8. Go for a swim or relax in the spa

Things to do in Helmsley

Helmsley is the only place in Yorkshire that has a heated public outdoor pool so you can enjoy swimming in the open air during your short break or holiday. There are family-friendly sessions at Helmsley Open Air Pool where you can have fun splashing around with the kids, and adult-only swims when you can get some proper exercise within the marked lanes of this 25-metre pool. 

Also in Helmsley is the wonderful Verbena Spa which is part of the town’s Feversham Arms Hotel. Facilities at the spa include a heated outdoor pool and jacuzzi within the spa’s pretty courtyard area and a relaxing aromatherapy room that is specially infused with essential oils. 

The unique Heat Experience at the spa features a journey through the spa’s various relaxation spaces which, on top of the aromatherapy room, include a saunarium, steam room and monsoon shower. Treatments available include massages, facials, body wraps and manicures so you can leave the spa looking and feeling your very best. 

9. Visit the historic Duncombe Park

Duncombe ParkImage credit: Berwickswan


One of Yorkshire’s grandest country estates, Duncombe Park is surrounded by around 450 acres of gardens and woodland on the outskirts of Helmsley. The 18th-century stately home was used as Misselthwaite Manor in the 2020 adaptation of The Secret Garden and you can explore the gorgeous grounds and gardens to discover a Father Time sundial and tunnel of trees that were both featured in the film.

  • Entrance to the extensive parkland that surrounds Duncombe Park costs just £1 and there are wildflower meadows, woodland walks, riverside strolls and waymarked nature trails to follow.   
  • The formal gardens which include terraces with wonderful valley views, temples and a fragrant secret garden are open to the public for eight weeks each summer. 
  • Also housed at Duncombe Park is the National Centre for Birds of Prey visitor attraction where you can walk with hawks, get up close to owls and watch falcons swoop directly into your gloved hand. The National Centre for Birds of Prey a great day out for visitors of all ages with three separate flying areas where you can watch different demonstrations throughout the day. 

10. Take your dog to the pub

Things to do in Helmsley

There is a good selection of dog-friendly North York Moors pubs where you can spend time catching up with friends and family with four-legged friends relaxing by your side. A visit to the pub is a great way to round off the day after enjoying a scenic walk in the North York Moors countryside. Here are some of our favourite dog-friendly Helmsley pubs:

Summats Brewing

This small pub is part of the Helmsley Brewing Company and you can sample a range of beers brewed on-site that includes the Yorkshire Legend bitter and the Helmsley Honey golden ale. Dogs are even welcome to join you on a tour of the brewery and there is a lovely beer garden to relax in.

The Feathers

With an extensive wine list, hand-crafted cocktails, daily afternoon tea options and a selection of seasonal dishes on the food menu there are lots of reasons to visit The Feathers in Helmsley. The bar area has lots of character thanks to exposed wooden beams and dogs can happily sit by your feet as you enjoy a drink (or two).

The Royal Oak

Dogs and their owners will be given a warm welcome at The Royal Oak, a traditional pub that’s right in the heart of Helmsley. Enjoy hearty food and a good selection of beers in the comfortable bar which is kept nice and cosy by a roaring open fire.

Plan your Helmsley getaway

Things to do in Helmsley

If you have been inspired to visit Helmsley and the surrounding North York Moors National Park, you’ll find a selection of gorgeous holiday homes that make perfect bases for exploring. Alternatively browse our full range of Yorkshire cottages and start planning your next UK getaway to this wonderful part of the world.


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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