My Britain: Oswestry

The history of Shropshire's old market town of Oswestry dates back to its origins as an Iron Age hill fort some 3,000 years ago. Known as the town where England meets Wales, it's perfectly nestled just five miles from the border between both countries, offering the opportunity to explore the cultures of both sides of the border.

Surrounded by historic castles, spectacular industrial heritage and pretty countryside, it also encompasses the Unesco World Heritage site of Pontcysyllte Aqueduct and is known for its heritage steam railways. We spoke to residents of this characterful town for a flavour of life in Oswestry. 

Sophie Dillon, 49, is the business owner of Old School House

Sophie Dillon owns Old School House, a cafe, restaurant and bar

Though I was born in Oswestry, I was itching to live a city life from the age of 18, and I did just that, living in Liverpool, Manchester, London, Melbourne and Perth. At some point, I yearned for my home town and to be near my family again. 

Oswestry is so pretty, we have beautiful walks and cycle routes, and it’s got a big attitude for a little town! There are some great independent businesses here, and they are growing. Being an Oswestry resident brings a lovely support network of friendly locals who enthusiastically support small businesses in the town. There are lots of activity groups who run, cycle, play tennis, knit, and even just drink coffee together.

My business, Old School House cafe, restaurant and bar, resides in the second oldest grammar school in the country, Oswestry School, established in 1407 by David Holbache. It oozes character and charm with its beamed walls and ceilings, wonky timber floors, and stunning south-facing walled courtyard. In its time, it has been a school, a toy museum, four residential cottages, and home to a tourist information centre. I took it over in 2021 and opened a fully licensed café/restaurant/bar, offering contemporary food menus (day and evening), craft ales, a lovely wine list, award-winning coffee, homemade cakes, locally-produced gelato and much more! We grow our own fruit and vegetables on-site, all of which gets used in the restaurant, and we are a registered Sustainably Run Restaurant, of which we are very proud.

The hill fort with its spectacular views

Oswestry is my home town, I had a strong connection to the Old School House building as I went to Oswestry School myself. There are plenty of discerning residents in the town who I was confident would appreciate the quality and quirkiness that the Old School House brings.

I have a few favourite spots in Oswestry. Pont Duncan, where the road goes over the river at Morda, is one. I have so many childhood memories of summer days, picnics, bike rides, and rope swings over the river. Also up on the Hillfort, where the views are really spectacular.

Rob, 61, Melissa, 60, and Hannah Lucks, 34, are owners of Chilton House B&B

Rob, Melissa and Hannah

Rob: My parents bought a hotel in 1979 while I was studying hotel management at college. I came back from college to help out at weekends and on holidays and stayed on.

Melissa: I came to work here and stayed in the hotel, met Rob and then we got married!

Rob: We worked with the parents for over 20 years but when Pops was ready to retire, we were ready to do our own thing and opened a restaurant in the town centre. After that we wanted to take a step back a bit and decided to transform our home into a B&B. Our daughter Hannah was born here. She has a very unusual syndrome and being so close to the Robert Jones and Agnes Hunt Orthopaedic Hospital meant that, in her early years, she had access to specialist care and support at this world famous hospital. Oswestry is such a safe, friendly and bustling town. There is so much happening for such a small place. Oswestry is one of those places that people come to by accident but once they arrive, they don’t want to ever leave.

Chilton House was our home before we turned it into a B&B. It’s a large Victorian house, a few minutes' walk from the centre of town. There are lots of original features and we wanted to celebrate that but add some quirky décor too. There are just three rooms for guests and each is completely different. It’s the fantastically interesting people we meet that make running a B&B in Oswestry special. Once they get to know the town, people usually want to return. They arrive as guests but always return as friends.

On a sunny day, there is nowhere better than our large garden and we love entertaining guests out there. It’s so peaceful even though we are so close to the town centre and it's a real sun spot.

A smiling market trader © John Hayward / Alamy Stock Photo

Oswestry is one of those places that whenever you walk into town you usually meet someone you know and they have time to stop and chat. It may be the second largest town in Shropshire but it has that small town feel. Oswestry is a real market town that has lots of independent shops and the market is a great attraction. The pub scene is really good too. There used to be over 100 pubs which is a lot for a small town! There aren’t so many now but what we do have is an eclectic mix of independently owned, traditional pubs. Having a local brewery and distillery on the edge of town means there are pubs that specialise in real beer but others do pub grub and there is a really vibrant music scene building again now the pandemic is ending. 

Rob Williams, 42, is the chairman of Cambrian Heritage Railways

Rob Williams has been involved with Cambrian Heritage Railway since 1996

I can’t think of any reason to leave Oswestry. It’s a small town and, when you are there, you usually recognise someone—friends or family. It’s a Welsh town in England and has the best of both cultures. I love that it is not only a market town but also a railway town. Our history has been shaped by both those things.

For me, being an Oswestry resident is very much being a part of the culture of the town. My interest in the heritage railway goes back to my teens and I enjoy that the railway history has created the modern town. 

The Oswestry spirit has been forged by the border connection. It has been confrontational in the past but now it celebrates the mix of the two lands. We’re good at getting things done, like the railway re-opening. It has taken a long time but there was always the determination and perseverance to make it happen.

I am chairman of Cambrian Heritage Railway and have been involved since 1996. The railway was once the biggest independent railway in Wales and yet its headquarters were in Oswestry in Shropshire, England. The railway changed the face of Oswestry when it was built, doubling the size of the town. 

It has been a privilege to be part of the group of volunteers that have re-opened the first one and three quarter mile track to run trains since 1966. In 1860, they said that no other town in England benefited from the arrival of trains as much as Oswestry. We are hoping that the re-opening of the railway will emulate that and bring a new generation of visitors to the town and that they will want to see more and stay longer. 

We now have not only a regular train service at weekends but also a fascinating museum of railway heritage, the original booking office and waiting room at Oswestry and the new station down at Weston Wharf. Every ticket is a day rover so visitors can come and go all day if they want to. The railway is a real community asset and we want locals and visitors alike to enjoy it.

I am a great people watcher and there are so many spots in the town centre that I enjoy. Festival Square, with the Borderland Farmer statue, is one and the town centre park with its beautiful flower displays is another. 

For more information head to visitshropshire.co.uk