Oswestry offers a wide selection of independent restaurants showcasing high‑quality local produce. The town is also known for its historic pub culture. The Bailey Head, winner of the 2025 CAMRA Pub of the Year award, sits at the heart of the town, and several traditional pubs can still be found along the high street.

The local live music scene continues to grow, with regular performances and opportunities to enjoy locally brewed drinks. Oswestry is home to the award‑winning Henstone and Stonehouse brewery and distillery. The brewery is now connected to the town centre by the heritage railway—providing a unique journey to Weston Wharf for food and refreshments.

Fans of international flavours will also find a choice of Chinese and Indian restaurants throughout the town.