11 UK Towns With Unforgettable Main Streets
In Wells, 15th-century water channels still run alongside the pavement of the High Street. In Stratford-upon-Avon, one Tudor row has served as a prison, a Shakespeare family home, and an inn. In both towns, the oldest building sits a short walk from the nearest coffee shop. Here are eleven UK High Streets where that mix of old landmarks and everyday shops is worth the trip.
Kirkwall
Off the North coast of Scotland lies the Orkney Islands, a minor archipelago of seventy islands. Kirkwall is the largest town in the archipelago, situated right in the middle of Mainland, its largest island, and home to what was deemed Scotland's "Most Beautiful High Street" in a public poll.
Kirkwall's main shopping route is centered on Bridge Street, Albert Street, Broad Street, and Victoria Street, beginning in the northeast of the town center, only a few blocks from the bay, and winding down to the historic St Magnus Cathedral, an immense sandstone landmark with roots in the 12th century. Along these streets, countless restaurants and shops open their doors year-round to visitors. If you find yourself there on a sweltering day where even the breeze from the bay can't cool you down, consider stopping in to Sinclaire's Sweets for a nice ice cream break!
Stratford-upon-Avon
Any literature lover will immediately recognize Shakespeare's hometown, and any traveler searching for the best small town stretches in England will be sure to remember the name of Stratford-upon-Avon. Like most towns in the UK, the main stretch of Stratford-upon-Avon is called "High Street," the British equivalent of America's "Main Street."
The High Street of this 800-year-old town is lined on both sides with authentic Tudor buildings, now mostly filled with cafés, though some were once a prison, a home to Shakespeare's daughter, and a house tied to John Harvard, Harvard University's first major benefactor. Visitors can also stop near the corner of High Street and Sheep Street, where the Garrick Inn and Tudor World add more Tudor-era character to the town-center walk. This compact historic stretch might even inspire you to write your own plays.
Whitby
Whitby is an ancient seaport whose historic headland is best documented from the 7th-century abbey onward. Begin with your feet at the top of the Abbey hill, looking over the town and the port. This great ruined structure is one of the Whitby sights that helped inspire Bram Stoker’s Dracula. From there, walk down the 199 steps and emerge onto Church Street, one of Whitby’s historic old-town streets.
Near the lower part of town, the Captain Cook Memorial Museum offers another stop tied to Whitby’s seafaring history. The cobblestone streets will take you through alleys, by homes, around buildings that have stood since the 15th century. As you snake your way through the narrow historic streets, you may find yourself at the end of the road, facing Whitby's Whale Bone Arch, which traps the whole town in a picture-ready frame. Be sure to get a picture beside the Whalebone Arch and the nearby bronze Captain Cook statue, which commemorates Cook separately.
Knaresborough
Knaresborough is a small town and civil parish in North Yorkshire, about a forty-minute train ride from Leeds. With no confirmed date of founding, sources for the town as a trading market date back to 1100 CE. That same trading spirit continues to flourish in this medieval town.
A trip down its unique main street includes views of the Knaresborough Viaduct, an impressive bridge for passenger trains which spans the Nidd Gorge, and time along the beautiful waterfront of the River Nidd itself. The real appeal of Knaresborough's High Street, though, is its thousand-year-old market spirit, centered around the historic Market Cross and within easy reach of Knaresborough Castle.
Bibury
For those familiar with UK passports, Bibury's Arlington Row, built in the 14th century as a wool store and later converted into cottages, might look familiar. Along Arlington Row runs the river Coln, which helps to keep the village's iconic greenery evergreen.
A trip down Bibury's main road is unforgettable because it feels like stepping into an older version of the Cotswolds. Nearby, visitors can also stop at Bibury Trout Farm, one of the village’s best-known attractions, or step inside St Mary’s Church, a Saxon church close to the village center.
Stamford
No street in the UK offers quite the same atmosphere as Stamford's compact High Street, where Georgian stone buildings frame the central walk. Reminiscent of a little Vienna and running parallel to the Welland River, Stamford's main drag, built from local limestone and framed by many 17th- and 18th-century buildings, is home to great spots such as Café Black and St Paul's Church on the eastern end.
That mix of stone buildings, cafés, churches, and arts spaces makes Stamford one of the more atmospheric stops on the list. While there, consider visiting the beautiful Stamford Arts Center, which sits only one block south.
Robin Hood's Bay
Just south of Whitby along the Yorkshire coast is a town built on an ancient parish with a history involving prehistoric man, Roman soldiers, Norwegian Vikings, and Saxons. Robin Hood's Bay is named after one of England's most famous folk heroes, and though the name's meaning has never been agreed upon, it is possible the town earned the title after being associated with heavy piracy and theft. In modern times, it is a quiet village which houses one of the UK's most amazing High Streets.
Starting at the sea where the stone foundations of the old parish part to let the waves crash on the sandy beach, it winds up King Street and New Road, passing through colorful stone and brick homes, getting steeper and narrower as it reaches the clifftop where the regional road begins. Along the way, visitors can browse small independent shops, look back toward the sea, or return to the beach, where rock pools and fossils add another reason to linger at the water’s edge.
Wells
Reminiscent of a small-town version of Canterbury, Wells in Somerset also boasts a formidable High Street, lined with Tudor buildings and medieval walls, all leading up to the awe-inspiring Wells Cathedral. This small city, which served as a filming location for the 2007 film Hot Fuzz, is also home to Vicars’ Close, described by Wells Cathedral as the oldest street in Europe still serving its original purpose, just two blocks from High Street.
Alongside High Street itself, besides the view of the imposing cathedral in the distance, you can stop at any of the small boutiques that fill the surrounding buildings. The King's Head Pub and Parsons Bakery add easy food stops along the central walk. While you enjoy the authentic medieval ambiance of the town, look to the side of the stone streets, where you'll see 15th-century water channels running parallel. When you're done, the cathedral and nearby gardens make an easy final stop.
Carrickfergus
The only entry from Northern Ireland is Carrickfergus in County Antrim, just 30 minutes north of Belfast. With a great Norman Castle guarding the sea on the town's south side, High Street breaks off from the castle and the quay, traveling north and wrapping around in a square. The town-center walk can also include Carrickfergus Museum on Antrim Street and the Flame Gasworks Museum in the Irish Quarter West, both of which deepen the town’s maritime and industrial history.
Carrickfergus (pronounced Karr-ik-Fur-gus) offers a smaller, quieter look at Northern Ireland’s coastal history. Pubs such as the Central Bar, Georgian brick buildings, tight alleys, and historic churches give the town center a compact but memorable coastal feel.
Ludlow
Another market town and civil parish, this time in Shropshire, Ludlow is an impressive planned medieval town which wraps around the River Teme. Like many medieval-era villages, Ludlow boasts an impressive castle on one end of its main street with a sprawling market in the square in front of it. On the other end of High Street, the town center opens into a network of narrow alleyways that disperse in every direction.
Walk through the Ludlow town walls, which began construction in 1233, crossing paths with countless Georgian and Tudor buildings and taking in the architectural history before stopping for a picture at St Laurence's Church or for a meal at the Blue Boar right in front of the castle walls.
Crickhowell
Our final stop is a town in Wales with only 2,100 people. Nestled into the green hills of Powys, near Abergavenny and its railway station, Crickhowell is a market town named for the nearby Iron Age hillfort of Crug Hywel.
Crickhowell sits between the River Usk and Table Mountain and features an award-winning High Street, where one can visit bookstores such as Book-ish or eat at restaurants like The Courtroom Cafe, all while enjoying the Georgian facades that take you back to the pastoral past of the British Isles. The Dragon Inn, a coaching inn on High Street, adds another historic stop for food or a drink along the same central stretch.
Why These UK High Streets Stay With Travelers
Across the UK, historic high streets still shape the way many small towns, villages, and compact cities are experienced. Haworth, Rye, and Totnes are also worth considering, but these eleven streets offer a strong starting point for travelers drawn to historic town centers. Whether through the limestone streets of Stamford or the history-filled center of Stratford-upon-Avon, these High Streets are more than paths for cars to drive on; they are places where local history still shapes the walk. So, next time you're in the UK, these roads offer a clear place to start.
