These Towns In The UK Have The Best Main Streets
The United Kingdom (UK) is known for so many things, from its stunning scenery to its millennia-old historic sites and from its warm and welcoming people to its fascinating cultural traditions. Connecting everything in this small island nation is a network of historic roads, some dating back 2,000 years to Roman times, around which entire communities evolved. Today, these small towns are home to charming Main Streets (or “High Streets,” as they’re known here) that boast centuries-old architectural treasures just begging to be explored.
Across England, Scotland, Wales, and Northern Ireland, the best of these charming High Streets offer no-end of fun. Whether you enjoy hunting for treasures in old antique shops, exploring local landmarks and historic sites, or hanging out with the locals in a great old pub, these UK towns have some of the best Main Streets you’ll ever see.
Helmsley, North Yorkshire
Helmsley is a picturesque market town in North Yorkshire near the bigger city of York, just 25 miles to the south. One of the prettiest High Streets in Northeast England, it marks the start of the Cleveland Way, a National Trail stretching 109 miles across the scenic North York Moors and along some of the county’s most spectacular coastline. High Street highlights include the Helmsley Arts Centre which regularly hosts plays, concerts, and film screenings. Annual events like the Helmsley Folk Weekend in late summer draw musicians from across the region to perform in various venues across town, including the Arts Centre and other High Street venues.
Just a few steps away from the main drag you’ll find yourself facing the impressive Helmsley Castle, built in the 12th century and later partially transformed into a comfortable Tudor mansion in the 1500s. A short stroll away, the Helmsley Walled Garden, originally constructed in 1759 to supply fruit and vegetables to nearby Duncombe Park, offers gardening workshops along with the chance to explore the heritage orchards and gardens.
St. Andrews, Scotland
Located on the east coast of Scotland and a 90-minute train ride northeast of Edinburgh, St. Andrews is famous as the home of The Old Course, the world’s oldest golf course. This university town also boasts a historically rich High Street that’s lined with centuries-old stone buildings that serve as a quaint backdrop as you make your way to nearby attractions like the ruins of St. Andrews Cathedral and the adjacent St. Andrews Castle, the latter offering superb views over the North Sea.
The British Golf Museum is also just a short walk away for those curious about the sport’s origins, while the University of St. Andrews campus, founded in 1413, is fun to explore on foot from the High Street. Another St. Andrews’ attraction is The Byre Theatre, a modern performance venue on Abbey Street with a regular schedule of plays and concerts. Visiting in shoulder season? Consider timing your arrival to coincide with the annual St. Andrew’s Day celebrations on November 30, when bagpipers take to the streets and free cultural events are hosted around town and along the high street.
Chipping Campden, Cotswolds
Ask anyone in the UK where you’ll find the most quintessentially English towns, odds are they’ll say in the Cotswolds. Situated in Gloucestershire, Chipping Campden is 100 miles west of London and boasts a High Street with well-preserved limestone buildings dating back to the 14th century. One of the most distinctive is Market Hall, built in 1627 and still standing at the center of the High Street. Nearby, historic Grevel House is recognized as one of the earliest “great houses” in Chipping Campden, dating to around 1380.
Also along the High Street, the Court Barn Museum details the work of the Arts and Crafts movement that thrived in this region during the late 19th and early 20th centuries. A fun time to visit is during the Cotswold Olimpick Games, held on the May Bank Holiday since the early 1600s and which in 2025 celebrates its 413th anniversary. Highlights of this quirky event include sack races, wrestling, and the notorious “shin-kicking” contest (something you’ll want to watch rather than participate in).
Conwy, Wales
Set against the scenic backdrop of the Conwy estuary in North Wales, this walled market town is easy to get to from Liverpool, a journey of around 55 miles. Though perhaps best known for the UNESCO-listed Conwy Castle, the High Street itself is a historical treasure that resonates with medieval charm. Shoppers are spoiled for choice here, with retailers such as Baravelli’s chocolate shop, an award-winning artisan chocolatier; the Royal Cambrian Academy, showcasing Welsh art; and excellent tea rooms such as the Conwy Pantry (take a few Welsh cakes home with you!).
One of the most photographed spots in town is The Smallest House in Great Britain. Tucked along the Quay near High Street, this bright red, 3.05 by 1.8 meter (10 feet by 6 feet) tiny home is said to have been lived in until 1900. The Conwy Food Festival in October is a great time to visit High Street Conwy, especially if you have a hankering for fresh seafood and locally brewed ales. Speaking of beer, spring and autumn see travelers turning up for the Conwy Real Ale Trail, which includes participating pubs across the town.
Enniskillen, Northern Ireland
Located 65 miles southwest of Belfast, Northern Ireland’s capital, Enniskillen’s High Street stretches through the heart of the town and provides easy walking access to attractions such as Enniskillen Castle. Built by the Maguire chieftains in the 16th century, this impressive castle complex houses the Fermanagh County Museum and the Inniskillings Museum, both of which explore local heritage. Just a little farther along, St. Macartin’s Cathedral is worth seeing for its striking spire and regimental flags. For those looking to shop, The Buttermarket displays locally produced souvenirs including ceramics, textiles, and artwork.
A highlight of the town’s cultural calendar is the Enniskillen Drama Festival, typically held in March at the Ardhowen Theatre and featuring amateur dramatic productions from across Ireland. Another crowd-pleaser is the Fermanagh Live Arts Festival in early October, showcasing live music and workshops in and around Enniskillen’s High Street.
Rye, East Sussex
A personal favorite (I lived near here in my youth), the town of Rye is one of the prettiest places to visit in Southeast England. Once a major port serving the English Channel, boaters and fisher folk can still offer access to the sea via the River Rother. Rye is well-known for its medieval and Tudor architecture, including the Ypres Tower, built in the 13th century as part of the town’s original fortifications. It still offers commanding views over the town’s rooftops and surrounding marshlands (you can learn more about it at the nearby Rye Castle Museum). Just a short walk away lies St. Mary’s Church, notable for its unique clock mechanism dating back to the 16th century.
Along the High Street, you’ll encounter specialty shops like Grammar School Records, popular for its rare vinyl and CD recordings, and tea shops like Fletchers House, built in 1579 and serving yummy cream teas (ask for a patio seat). The town’s especially lively during the Rye Arts Festival in September which features performances, exhibitions, and literary talks. Another great time to visit is during the Rye Bonfire, a traditional boat burning and torchlit parade. It’s also known as the Great Rye Fawkes Pageant after the infamous rebel who tried burning down the country’s parliament buildings in 1605.
Totnes, Devon
Situated on the River Dart in Southwest England, Totnes is just 25 miles from the historic naval port of Plymouth and makes for a great day trip from its larger neighbor. Steeped in history, its High Street is perched on a hill, offering visitors a chance to meander through a collection of independent shops, galleries, and eateries as they make their way to the town’s Norman fortress. Now maintained by English Heritage, Totnes Castle dates to the 11th century and provides commanding views of the town and surrounding countryside.
You’ll also want to visit the Butterwalk, a 17th-century arcade famed for its timber-framed buildings and distinctive overhangs. Other shopping opportunities can be enjoyed at Totnes Market, held on Fridays and Saturdays in the Civic Hall Square. The High Street is also the scene of community events like the Totnes Christmas Market and Late-Night Shopping on Tuesdays throughout December.
The Final Word
From Scotland’s storied university town of St. Andrews to the Welsh fortress community of Conwy, these seven destinations demonstrate that the UK’s best Main Streets (aka, “High Streets”), are so much more than simply thoroughfares. Each town’s High Street brims with distinctive shops, historical buildings, and cultural gatherings that help keep old traditions and heritage alive. So if you’re planning a trip to the UK, be sure to include at least one or two of these beautiful downtowns on your travel itinerary.
