Oswestry Landmarks Round

GPX files and a route map available here!

You’ll set off from the welcoming Beech Tree Café in the centre of Oswestry (look for the OLM Logo on the wall), the perfect place to fuel up before heading to the medieval ruins of Oswestry Castle, once a fortress at the heart of power struggles between England and Wales. Then it’s on to Oswestry Train Station, a charming reminder of the town’s railway past, before climbing to the ancient Iron Age hillfort, offering panoramic views and a glimpse into life over 2,000 years ago.

From there, you’ll pass the graceful Brogontyn Hall, a stately home with deep roots in local history, before striding out across the open expanses of Oswestry Racecourse, now a peaceful stretch of the Offa’s Dyke Path.

At around mile eight, you’ll reach the Kettle House Café at the Old Mill – the perfect halfway haven. With 24-hour toilets, an honesty café offering hot and cold drinks, cake, feminine hygiene products, and even camping or B&B options, it’s a unique place to pause, recharge, and soak up the friendly atmosphere before pushing on.

The route then leads to Trefonen, a former mining village with its own warm welcome. Here, you can grab supplies at the local post office or enjoy hot food and well-kept ales at The Barley Mow – an ideal mid-route pit stop before tackling the climb to the Moelydd trig point, where sweeping views across the Shropshire and Welsh hills await.

On the return, you’ll pass Oswald’s Well, steeped in legend, before entering the heart of the town through Cae Glas Park, where the statue of poet Wilfred Owen stands in quiet reflection. Finally, it’s back to the Beech Tree Café for that well-earned drink and slice of cake.