Helmsley
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- Helmsley
One of North Yorkshire’s most popular market towns (officially - it won the Great British High Street Award’s best market town category), Helmsley is somewhere everyone should visit at least once in their lifetime. Although if you go once, you are likely to go back time and time again - a visit to this picturesque town, which has so much going on, feels like a breath of fresh air.
The market town is a perfect destination for those who love the great outdoors with a wealth of walking and cycling routes through the North York Moors National Park on its doorstep. The Discovery Trail showcases local history on an easy loop, while cyclists can enjoy routes like the Helmsley to Rievaulx Abbey ride and the challenging North York Moors Cycleway, passing through heather landscapes and hidden valleys on quieter roads. One of the highlights is the Cleveland Way, a renowned national trail that starts right in Helmsley. If you fancy taking a dip to cool off, the town’s open-air pool is a refreshing option in the summer months.
If you prefer a more leisurely pace, take a trip back in time at the town’s castle, admire the stunning blooms and floral arches at the walled garden, marvel at spectacular birds of prey displays at the nearby estate, or wander stunning National Trust sites just outside of town. Take a stroll around the town and browse the town’s many independent shops and boutiques, savour a bite to eat in the welcoming cafés and bakeries, delicious delis and welcoming pubs and restaurants. When it’s time to rest after a day exploring, choose from a range of quality accommodation from spa hotels to cosy cottages.

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Businesses in Helmsley
Studford Luxury Lodges
Tucked away in a quiet corner of the North York Moors National Park, just… Tucked away in a quiet corner of the North York Moors National Park, just four miles from the market town of Helmsley, these luxurious designer tree…
Holly-Garth Holiday Cottage
Holly-Garth is a superbly equipped 4 star holiday cottage near the centre… Holly-Garth is a superbly equipped 4 star holiday cottage near the centre of the pretty town of Helmsley, on the edge of the North York Moors. We…
The Black Swan Helmsley Restaurant
Great food is at the heart of great hospitality and our restaurant –… Great food is at the heart of great hospitality and our restaurant – overlooking the walled garden – is at the heart of the hotel.
Helmsley Walled Garden
This tranquil and historic five acre garden is beautifully laid out in… This tranquil and historic five acre garden is beautifully laid out in small intimate garden spaces to explore. Enjoy the cool of the foliage border,…
Cliff Cottages - Frankel Cottage
The location and surrounding views are breathtaking during all seasons.… The location and surrounding views are breathtaking during all seasons. It’s a very peaceful place despite being so close to the centre of town.
Black Swan at Oldstead
The Black Swan at Oldstead is a restaurant with rooms created by the Banks… The Black Swan at Oldstead is a restaurant with rooms created by the Banks family who have lived and farmed around Oldstead for centuries.
The Pheasant Hotel Restaurant
16 bedroomed award-winning country hotel 16 bedroomed award-winning country hotel
Ampleforth Abbey
Set in acres of beautiful scenery, Ampleforth Abbey is home to the largest… Set in acres of beautiful scenery, Ampleforth Abbey is home to the largest Benedictine community of monks in the UK. We extend a warm welcome to…