The 10 Prettiest Towns in North Yorkshire

As one of the most beautiful regions in the UK, it comes as no surprise that there is an abundance of pretty towns to visit in North Yorkshire. After all, the area is world-renowned for its pristine and unspoilt natural scenery.

The stunning landscapes, much of which fall within the North York Moors, feature a captivating mix of ancient woodlands and rugged coastlines, peppered with charming towns and villages. With so many picturesque spots to visit in the area, it can be difficult to know where to begin when planning a trip.

To ease the planning process and help you plan the perfect trip, we have shared the 10 prettiest towns in North Yorkshire. 

North Yorkshire Scenic Towns

Thornton-le-Dale

Thornton-le-Dale is undeniably one of the prettiest towns in North Yorkshire and is even often celebrated as the most picturesque village in all of Yorkshire. Located about 12 miles from Scarborough, this quaint little village is a paradise of thatched cottages, immaculate gardens, and a quaint stream that runs through it.

The town’s main square is home to the famous Chocolate Factory, where you can indulge in locally-made truffles and a variety of chocolate delights. Don’t miss the breathtaking Grade II listed church during your visit to this quaint North Yorkshire village.

Perched dramatically on a hill, the 14th-century church offers dazzling views over the village. Thornton-le-Dale is also surrounded by enchanting woodland, adding to its picturesque scenery.

You can follow an accessible trail that takes you around the village, past fascinating tree carvings and ponds teeming with wildlife. You’ll come across plenty of picturesque 17th-century almshouses during your time in Thornton-le-Dale. They create the postcard-perfect backdrop for your visit.

Aysgarth

Aysgarth is one of the best towns to visit in North Yorkshire. The magnificent little village lies in Upper Wensleydale in the Yorkshire Dales. It is home to sprawling green hills and several stunning waterfalls, making it a wonderful place to explore while holidaying in England.

The waterfalls are a major highlight, especially Aysgarth Falls which is famed for its dramatic three-step cascades that plunge into the River Ure. The site lies just a stone’s throw away from the town and is a must-visit during your stay. 

Aysgarth also has a gorgeous church that has a fascinating history, having survived a ransacking by Henry VII’s men in 1537. The town itself is small, with under 200 inhabitants but there are still lots of amenities to enjoy in this beautiful part of Yorkshire, including public houses and tearooms. 

When you fancy a walk, you can visit the nearby wooded valley which bursts into bloom with wildflowers in the spring and summer. Bolton Castle is also a popular place to visit when staying in Aysgarth. Lying just four miles to the north, the awe-inspiring 14th-century structure traces back to the 14th century.

Kettlewell

Kettlewell is one of the most beautiful North Yorkshire towns to visit. It features a blend of charming 17th and 18th-century houses, which lie clustered along a valley in the Yorkshire Dales. Kettlewell is one of the best towns to visit in North Yorkshire for hikers as it has a wealth of wonderful trails to choose from.

The routes include everything from gentle, picturesque strolls to more challenging hikes like the ascent of Coverhead Pass. Kettlewell is also a great place to visit for cyclists who can explore the quiet country lanes that offer glorious views over the surrounding countryside.

When you work up an appetite, check out the town’s local pubs. Here you enjoy a hearty meal at one of the town’s local pubs, where you can savour traditional home-cooked dishes and sample local Yorkshire ales. For a lighter option, visit one of the town’s cosy tearooms for warm coffee, tea, and freshly baked pastries.

Historic North Yorkshire Towns

Hutton-Le-Hole

Hutton-Le-Hole is certainly one of the prettiest towns in North Yorkshire. Hidden away in a hollow in the Tabular Mountains in the North York Moors National Park, this historic little haven serves up the dreamiest countryside scenery. 

A little river called Hutton Beck winds through the town before merging with the enchanting Fairy Call Beck.  These idyllic waterways wind through Hutton-le-Hole’s lush green pastures, where sheep graze and picnickers relax on either side.

The town’s Main Street is quaint and peaceful, with a few choice shops, restaurants, cafes and accommodation options. One of the best places to visit during your time in this pretty North Yorkshire town is The Ryedale Folk Museum. 

This open-air museum spans a 6-acre site and includes over 20 heritage buildings. Visitors can explore traditional blacksmith workshops, thatched manor homes, and mediaeval cottages, uncovering the fascinating history of those who lived in the area many years ago.

​​Osmotherley

If you’re looking for pretty towns in North Yorkshire, you can’t go wrong with Osmotherley. This picturesque destination is ideally placed just between the Cleveland Hills to the north and the Hambleton Hills to the south, on the edge of the North York Moors.

The village is backdropped by thick, enchanting woodlands, rolling hills and pristine reservoirs. With such glorious natural scenery on offer, it comes as no surprise that the village is popular amongst hikers and outdoor enthusiasts.

Beyond its breathtaking landscapes, Osmotherley is also excellent for history buffs. The village is home to the 12th-century St. Peter’s Church and historic almshouses. Additionally, there are several charming pubs and restaurants, some dating back to the 16th century.

If you time your visit to this small North Yorkshire town right, you can even experience the annual Osmotherley Show, a traditional agricultural event that has been held since 1791.

Market Towns in North Yorkshire

Middleham

If you’re on the lookout for picturesque market towns in North Yorkshire, Middleham is a wonderful option. It is located in Wensleydale Valley. Despite its size, this little town is home to an abundance of exciting visitor attractions. 

Middleham boasts a historic castle dating back to the 12th century, which is sometimes hailed as the  ‘Windsor of the North’. It was the childhood home of King Richard III and has an impressive great tower, or keep, which stands 15 metres high, 24 metres wide, and 32 metres deep, making it one of the largest keeps in the country.

The castle also houses an incredible replica of the Middleham Jewel, a remarkable 15th-century pendant adorned with a large sapphire.

The town features two bustling market squares, lined with lively pubs, quaint antique shops, and impressive historic buildings, all set against the magnificent backdrop of the Yorkshire Dales countryside.

Middleham is also renowned for its horse racing heritage as it is home to several racing stables. If you’re lucky, you may be able to see the racehorses in action as they can sometimes be seen striding through the market square.

Helmsley

Helmsley is one of the best market towns in North Yorkshire as it is the only one that lies within North York Moors National Park. As you would expect from its location, it is blessed with heavenly surrounding natural scenery. 

The town is situated on the banks of the River Rye and has a fantastic range of walks on its doorstep. They’ll take you by idyllic little streams, beautiful woodlands and even dramatic abbey ruins. Helmsley is also home to the remains of the 12th-century Helmsley Castle. The striking landmark boasts a 100-foot-high tower, bronze archers and mediaeval remains. 

You may also wish to pay a visit to Hemsley’s Walled Garden to stroll by stunning flowers, water fountains and greenspaces before enjoying some homemade cake at the cafe. 

You’ll find the streets of Helmsley to be buzzing with atmosphere, thanks to its superb selection of restaurants, tea rooms, marvellous pubs and independent boutiques. In fact, this picturesque little town even boasts a Michelin-starred restaurant for those fancying a spot of fine dining during their getaway.

North Yorkshire Coastal Towns

Robin Hood’s Bay

Robin Hood’s Bay is a spectacular fishing village in North Yorkshire. The picturesque town clings dramatically to a cliff overlooking the North Sea. Its terracotta-topped houses cascade down the rugged coastline, melting into the waters beyond.

The town itself comprises a maze of cobblestone passages lined with charming little cottages. Robin Hood’s Bay has a fascinating history, having once been brimming with smugglers who were bringing in contraband such as tobacco and gin using boats hidden away in the harbour. 

They then snuck the items into the town through underground alleyways. You can learn all about the colourful local history at Robin Hood’s Bay Museum.

The town streets are lined with guest houses, fish and chip shops and tea rooms. At high tide, you can meander along the clifftop path for sublime vistas over the ocean. At low tide, a plethora of rock pools come into view and make for exciting areas to explore. 

Staithes

Staithes is one of the nicest seaside towns in North Yorkshire. The wonderful fishing village lies tucked away into an inlet along the coastline,  just 10 miles north of Whitby. It sits on the beautiful Staithes Beck, which flows into the North Sea.

The town’s peaceful, sheltered harbour is a dramatic sight, set alongside plunging cliffs and divine 18th-century cottages.  Enjoy the magnificent coastal views as you stroll along the shoreline, where fossils are commonly found.

Explore Staithes by wandering along its cobblestone alleyways and narrow ginnels, including Dog Loup, one of the narrowest streets in England. The town is also renowned for its history; the famous explorer Captain Cook worked here as an apprentice before embarking on his sea voyages.

While investigating Staithes, you’ll come across an array of craft shops, boutiques and galleries that make excellent places to pick up a memento of your time here. The town also has lots of cosy traditional pubs and restaurants where you can enjoy some tasty food and drinks by a roaring fire.

Sandsend

Sandsend is one of the best seaside towns in North Yorkshire. Here you’ll find a delightful coastal promenade with a three-mile sandy beach lined with peaceful, shallow waters. When the tide is out, lots of rock pools appear beneath the retreating waters and the marine wildlife can be seen strutting their stuff. 

The fishing village also has a plethora of great dining options to choose from when you fancy a bite. Many restaurants serve delicious, fresh seafood or traditional Yorkshire dishes made with local ingredients, including roast meats and seasonal vegetables.

Mulgrave Castle is a wonderful place to visit during your time in this tranquil North Yorkshire town. Hidden away in the stunning North York Moors, you’ll find a magnificent mediaeval fortress and uncover the castle’s fascinating heritage. 

Along with coastal walks along Sandsend Beach, you can also go surfing along Runswick Bay and learn about the coastal environment at the Yorkshire Beach School. With so much to see and do in this coastal town in North Yorkshire, Sandsend offers a fantastic escape for foodies, seaside and history lovers alike. 

Summary 

There are so many pretty towns in North Yorkshire to visit. From quaint villages tucked away amidst the rolling hills to vibrant market towns with castles and walled gardens, it’s hard to top the beauty on offer in this picturesque corner of the North of England.

Dreaming of visiting the prettiest towns in North Yorkshire? Take a look at our wonderful selection of lodges in the heavenly woodlands of Angrove Country Park and our luxurious resort in the village of Aysgarth.