These 13 Beautiful Medieval Cities and Towns in the UK Feel Like a Fairytale

One of the United Kingdom’s biggest draws is its rich history. This small yet fascinating nation comprising England, Scotland, Wales, and Northern Ireland has played host to Ancient Rome, the Celts, the Vikings, historic Kings and Queens, and more. Today, much of the nation’s history can be explored through its medieval towns and cities.

From York and Chester to Rye and Conwy, the United Kingdom is jam-packed with medieval delights begging to be discovered. To learn more, we’ve compiled a list of 12 beautiful medieval cities and towns in the UK.

The towns and cities we’ve selected are famed for their medieval architecture, unique charm, and many things to see. As someone who lives in the United Kingdom, they’re also some of my favorite places to visit.

Table of Contents

York

Let’s start this list with York, arguably the United Kingdom’s most iconic medieval city. This historic city is renowned for its breathtaking architecture, charming atmosphere, and rich history. With its Roman and Viking roots, York offers travelers an eclectic mix of history and culture. Better yet, the Shambles is widely regarded as the world’s best-preserved medieval street.

This quaint street, which inspired Diagon Alley in J.K Rowling’s Harry Potter novels, was mentioned in the Domesday Book of William the Conqueror in 1086. Many of the beautiful buildings in the Shambles date back to the 14th and 15th centuries. Other notable attractions in the city include the York Minster, the York City Wall, the JORVIK Center, and Clifford’s Tower.

Chester

Another mesmerizing medieval English city is Chester, a 2,000-year-old Roman fort surrounded by approximately 2 miles (3.2 kilometers) of towering defensive walls. Steeped in history, this gorgeous city is home to many examples of medieval and Roman architecture, including a Roman amphitheater that dates back to the 1st century B.C.

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When you’re not setting foot inside the Chester Roman Amphitheatre or walking along the city walls, get lost exploring the city’s beautiful cobblestone streets. You’ll never tire of admiring Chester’s well-preserved Tudor-style half-timber buildings. One major highlight is the Rows, a two-tiered shopping walkway dating back to the 13th century. You don’t want to miss the Chester Roman Gardens.

Edinburgh

While Edinburgh, Scotland’s vibrant capital city, is famous for the annual Edinburgh Fringe Festival, it also features a magical medieval Old Town bursting at the seams with stories to tell. As you cross the bridge from the New Town to the Old Town, you’ll be transported hundreds and thousands of years into the past.

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You’ll spend most of your time in the Old Town looking up at the imposing 900-year-old Edinburgh Castle, walking along the 12th-century Royal Mile in search of medieval delights, and exploring the city’s underground dungeons. We don’t know about you, but that sounds pretty spectacular. Must-see attractions include St Margaret’s Chapel, John Knox House, St Giles’ Cathedral, and Holyrood Abbey.

Crail

If you travel north from Edinburgh along the east coast of Scotland, you’ll come to a small medieval harbor town in Fife County called Crail. This picturesque harbor town is small but packs a punch with its rich history. For starters, the town, home to less than 2,000 people, is over 900 years old.

The town was granted its first Royal Charter in 1310 by King Robert the Bruce. As a result, it’s one of Scotland’s oldest Royal Burghs. The town hasn’t much to do, but its beautiful scenery, tranquil atmosphere, and gorgeous medieval houses are a joy to experience. Unsurprisingly, this is an excellent place to visit if you seek an escape from the daily grind.

Rye

12 Beautiful Medieval Cities and Towns in the UK Rye — © Rolf / Adobe Stock

The United Kingdom’s medieval towns also have much to offer, especially if you want to escape the hustle and bustle of the big cities. Rye, a charming English town in East Sussex, is one of the United Kingdom’s most impressive medieval towns. Reminiscent of something from our favorite fairy tales, Rye is a beautiful town with a charm that feels untouched by time.

Furthermore, it’s only a short drive from Camber Sands, one of England’s best beaches. During your trip to the hilltop town, you’ll fall in love with Rye’s postcard-perfect medieval architecture, scenic views, and narrow cobblestone streets. Significant points of interest in the town include Mermaid Street, Mermaid Inn, Rye Castle Museum, Rye Heritage Centre, and Lamb House.

Conwy

If you want to explore medieval Wales while also enjoying the nation’s impressive countryside, you must visit Conwy, a medieval walled market town in Conwy County Borough, North Wales. Easily one of Europe’s most magnificent medieval fortresses, Conwy has a vibrant harbor, a marvelous 12th-century castle, tall city walls, and quaint houses.

Interestingly, the town is also home to the Smallest House in Great Britain, a harborfront property measuring just 6 feet (1.8 meters) wide and 10.1 feet (3.07 meters) high. Things only get better, with Conwy only a short distance from the rugged mountains of Eyri (Snowdonia), the sunny seaside town of Llandudno, and the picturesque island of Anglesey.

Ludlow

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The following medieval destination on our list is Ludlow, a lovely market town in Shropshire loved for its medieval architecture, cozy pubs, and lush scenery. The 11th-century Ludlow Castle dominates the town. It offers a fascinating insight into English history and incredible landscape views. It’s also one of the first stone castles to be built in England.

Meanwhile, the town itself features a beautiful mix of Tudor-style half-timbered houses and Georgian buildings, giving Ludlow a distinctive appearance. Once you’ve explored the narrow streets in the town, head into the Shropshire countryside and enjoy leisurely walks in the hills. Afterward, walk back into Ludlow for some classic English pub grub in one of Ludlow’s many traditional pubs.

Carrickfergus

Across the water in Northern Ireland, you’ll find a picturesque medieval town called Carrickfergus. Located in County Antrim, this colorful town sits on the north shore of Belfast Lough, approximately 11 miles (17.7 kilometers) from the capital, Belfast. Carrickfergus is a gorgeous coastal town with lush scenery, vibrant houses, and authentic Irish charm. However, its crowning glory is the 12th-century Carrickfergus Castle.

Dominating the waterfront, this mind-blowing castle is a sight to behold. Furthermore, it played a pivotal role in various historic events. Built by John de Courcy in 1177, the castle was besieged by the Scots, Irish, English, and French. Today, it remains one of the best-preserved medieval structures in Ireland. Other must-see attractions include Carrickfergus Marina and Carrickfergus Museum & Civic Centre.

Norwich

Admittedly, Norwich isn’t one of the most famous cities in the United Kingdom, but that doesn’t mean you shouldn’t visit, especially if you love medieval history. Despite being one of the lesser-visited cities in England, Norwich claims to be one of the United Kingdom’s most complete medieval cities.

With meticulously preserved medieval architecture, beautiful cobblestone streets, ancient buildings, and a fascinating medieval castle to explore, it’s hard to disagree. Across the city, you’ll find magnificent medieval attractions, such as Norwich Castle, Elm Hill, Norwich Cathedral, Timber Hill, and Tombland. Other significant medieval buildings worth visiting include Stranger’s Hall, Dragon Hall, and the Guildhall. As such, you’ll struggle to see it all in one trip.

Stratford-Upon-Avon

Stratford-Upon-Avon is a breathtaking medieval market town in England’s West Midlands, specifically Warwickshire, with a history that dates back to the 7th century A.D. You may recognize this quaint town because of its association with William Shakespeare, a world-famous English writer. Shakespeare was born and buried in Stratford-Upon-Avon.

Visitors can still watch William Shakespeare’s plays at the Royal Shakespeare Theatre and visit the half-timbered Tudor-style homes he once called home. As you would expect, the town also features many charming medieval streets with shops and cafes. Besides its rich history, Stratford-Upon-Avon is well known for its outdoor activities, such as hiking, kayaking, and paddleboarding, which occur on or alongside the River Avon.

Oxford

The penultimate medieval destination on our list is Oxford, a 12th-century city in Southern England best known for its world-famous university. While Oxford is most famous for its 11th-century or earlier university, it’s also recognized as one of the United Kingdom’s most beautiful medieval cities. You’ll find grand establishments, luxurious houses, and mind-blowing medieval structures at every corner of the city.

With this in mind, it’s hardly a surprise that Wordsworth, J. R. R. Tolkien, and Richard Dawkins, along with princes, Nobel Prize winners, and famous artists, have all called the city home. Significant points of interest in Oxford include Oxford Castle & Prison, Pitt Rivers Museum, Oxford Botanic Garden, and Oxford University Museum of Natural History.

London

While most people associate London with towering skyscrapers, bright lights, lively food markets, and iconic attractions like the London Eye, it was once a medieval town. In fact, it was during the medieval period that London became the capital of England. Today, many of the city’s fascinating medieval landmarks remain.

Some of London’s most notable medieval attractions include the 11th-century Tower of London, the 11th-century Westminster Abbey, the 11th-century Westminster Hall, and the 14th-century Jewel Tower. However, one of my favorite ways to learn about London’s history is in London Dungeons. This entertaining attraction takes visitors on a journey through 1,000 years of London history and Medieval Britain while also putting you through some pretty scary activities along the way.

Cardiff

The final city on our list is Cardiff, the capital of Wales. Cardiff is a lively city known for its modern architecture, beautiful waterfront, and picturesque harbor. However, history buffs love the city most for its rich history, which dates back to the medieval period. Before Cardiff was a modern city, it was a medieval town.

The remnants of the city’s medieval past can be seen in its many castles, of which there are over 20. The city’s most iconic castle, Cardiff Castle, was originally built in the 11th century by Norman invaders. It sits atop a 3rd-century Roman Fort. Other must-see medieval attractions include Castell Coch, St. Fagans National Museum of History, and Llandaff Cathedral.