The Bailey Head is a Multi-award-winning pub.
Society of Independent Brewers (SIBA)
- Society of Independent Brewers (SIBA) UK’s Best Independent Craft Beer Pub/Bar – Rural: Winner 2020, Highly Commended: 2024 Finalist: 2023, 2022, 2021, 2018.
Campaign for Real Ale (CAMRA)
- Shrewsbury & West Shropshire CAMRA Pub of the Year: Winner 2024, 2023, 2018; Runner up 2022, 2020, 2019, 2017
- Shrewsbury & West Shropshire CAMRA Market Towns Pub of the Year: Winner 2024, 2023, 2022, 2020, 2019, 2018, 2017
- Shrewsbury & West Shropshire CAMRA Cider Pub of the Year: Winner 2024
- Shropshire CAMRA Pub of the Year: Runner up 2023, 2018
- Marches CAMRA (Shropshire and Herefordshire): Third place 2018
- CAMRA Good Beer Guide: 2024, 2023, 2022, 2021, 2020, 2019, 2018
TripAdvisor
Travellers’ Choice: 2022, 2020
Certificate of Excellence: 2019, 2018, 2017
Oswestry Pub Scene
Best Pub, Best Atmosphere, Friendliest Staff 2021
Best Landlord/Landlady 2023
Oswestry In Bloom
Public Houses and Hotels: Gold and Winner 2023, Silver 2022
Town Centre Commercial Premises: Gold 2023
Oswestry Life Magazine
Local Hero Awards: 2020 Winner Customer Service/Diversification
Dogbuddy/Rover
West Midlands Most Dog Friendly Pub: Winner 2017