Helmsley
- Places
- 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.

Discover Helmsley on our map

Businesses in Helmsley
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…
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…
The Black Swan Helmsley
The Black Swan Hotel at Helmsley is a historic inn, turned boutique hotel.… The Black Swan Hotel at Helmsley is a historic inn, turned boutique hotel. Right in the heart of one of the North York Moors’ prettiest towns, the…
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.
Sunset Cottages
Granary conversion forming 4 cottages & two flats on a quiet, secluded… Granary conversion forming 4 cottages & two flats on a quiet, secluded working farm. Set amidst the Howardian Hills with splendid views. Central for…
Rievaulx Moor Easy Access Walk
From the Forestry Commission car park on the B1257 north of Helmsley the… From the Forestry Commission car park on the B1257 north of Helmsley the route arcs around the northern edge of Rievaulx moor.
Howardian Hills
Designated a National Landscape, the Howardian Hills cover 77 square miles… Designated a National Landscape, the Howardian Hills cover 77 square miles of woods, farmland and historic parkland.
Ampleforth Abbey Tea Room
Situated in the beautiful grounds of Ampleforth Abbey, and a short walk… Situated in the beautiful grounds of Ampleforth Abbey, and a short walk from the Abbey Church, the lovely oak-panelled tea toom is furnished with…