- 2022 – Heritage Railway Association Award for Diesel Locomotion for Drewry Railcar No 2 – Winner
- 2022 – Heritage Railway Association Award for Outstanding Visitor Attraction – Runner-up
- 2021 – Red Funnel Award for the Island’s Best Large Visitor Attraction – Winner
- 2021 – Tripadvisor Gold Award
- 2020 – Isle of Wight Radio Best In Business Awards, Best in Tourism Award – Winner
- 2019 – Heritage Railway Association, Award for Outstanding Visitor Attraction – Winner
- 2019 – Heritage Railway Association, Morgan Award for Outstanding Achievement for the restoration of Oldbury Carriage No.10 – Runner up
- 2016 – Visit England Gold Accolade
- 2016 – Heritage Railway Association, large groups annual award for Train Story
- 2015 – Tourism South East Beautiful South Awards, Large Visitor Attraction of the Year – Silver Award
- 2015 – Heritage Railway Association, Publication & Media Best Magazine Award
- 2015 – Visit England Gold. Visit England Gold Accolade
- 2013 – Southern Railways Group Denys Fletcher Award, for Wootton and Smallbrook Junction stations
- 2012 – Tourism South East – The Beautiful South Awards for Excellence – Silver Award
- 2012 – The Queens’ Award for Voluntary Service. The MBE for volunteer groups
- 2010 – Winner – The UK’s Best Heritage Project – The National Lottery Awards 2010
- 2006 – Winner – Best Publicity Leaflet (Heritage Railway Association)
- 2002 – Winner – Heritage Railway Association Carriage & Wagon Competition – for LCDR 4-wheeled carriage No. 2515
- 2002 – Joint Winner – Southern Tourist Board Excellence in England Award
- 2000 – Winner – Independent Railway of the Year Award
- 1998 – Commended – Heritage Railway Association Best Restored Coach Competition – for carriage 2343
- 1995 – Winner – Independent Railway of the Year Award
- 1989 – Winner – Independent Railway of the Year Award
- 1988 – Runner-up – Independent Railway of the Year Award
- 1986 – Premier Award Winner – The British Rail Award – Best Restored Station Competition – for Havenstreet Station (Association of Railway Preservation Societies)
- 1986 – Winner – Best Preserved Carriage – for Carriage IWR No. 46 (Association of Railway Preservation Societies)
- 1982 – Certificate of Merit – Isle of Wight Conservation Award – for the Railway Refreshments Building
