Named after King Oswald of Northumbria, who died in 641 AD, Oswestry is steeped in history and his a wide selection of attractions to visit, both in the town centre and the surrounding countryside.

The remains of Offa's Dyke run just to the west of the town, and can be easily walked along the well-maintained Offa's Dyke Path. Previously the Dyke separated the ancient kingdoms of Powis and Mercia, roughly along the modern day border of Wales and England.

Attractions in or near Oswestry town centre include Castle Bank (the remains of Oswestry's old castle), St Oswald's Well and Oswestry Old Fort (one mile north of the town centre with commanding views over the countryside).

Other places to visit include the Attfield Theatre Company is a flourishing 99-seat theatre in the Guildhall in the heart of Oswestry.

Two societies have preserved the former railway line from Gobowen to Oswestry and beyond. The Cambrian Railways Trust is based in Llynclas, 5 miles south of Oswestry on the A483 to Welshpool, and operates steam services in summer; the Cambrian Railways Society operates in Oswestry station.

Oswestry's former railway station – once the headquarters of the Cambrian Railway – reopened as the Cambrian Visitor Centre in June 2006. Located near the centre of Oswestry, and open 7 days a week, the centre tells the story of the coming of the railways to the town, and also houses the Tourist Information Centre.

Experience Oswestry with Oswestry Guided and Themed Walking Tours – these guided tours are every Saturday throughout the year.

Park Hall Farm is a 130-acre working Victorian farm, with activities both inside and outside. Includes animals large and small, milking, lamb feeding, pony grooming, and cart rides. Just two miles from Oswestry, and one mile from Gobowen station.