In 1985 the club organised a charity ride to Gloucester’s twin town of Gouda in response to the visit by Gouda riders the year before. The Club was presented with a Church Warden’s clay pipe made by a master craftsman. It was mounted and is now the trophy awarded for the best overseas ride, as judged by vote at the AGM.
| Year | Winner | Location of ride |
|---|---|---|
| 2023 | Simon & Theresa Pollington | The Netherlands |
| 2022 | Alastair Goldie | Tuscany |
| 2021 | Not awarded | |
| 2020 | Not awarded | |
| 2019 | Alastair Goldie | Cyprus |
| 2018 | Pete & Sue Lloyd (tandem) | Holland |
| 2017 | Adrian Pearce | Haute Alpes |
| 2016 | Paul Bridges & John Flint | Spain |
| 2015 | Pete Lloyd et al | |
| 2014 | Graham Denny | Menali to Leh |
| 2013 | Graham Denny | |
| 2012 | Martyn & Ann Willliams (tandem) | Holland |
| 2011 | Gary & Julie Ridgeway (tandem) | Holland |
| 2010 | Derek Dowdeswell | Normandy Beaches |
| 2010 | Derek Dowdeswell | |
| 2009 | Ed Spurway | Pyrenees end to end |
| 2008 | Graham Denny | Rwanda |
| 2003 | Dave Lesser & Theo Brookes | |
| 2002 | Alastair Goldie & Matthew Utting | |
| 2001 | Nigel & Debbie Light | |
| 2000 | Theo Brookes | |
| 1998 | Alastair Goldie | |
| 1997 | Alastair Goldie | |
| 1996 | Alastair Goldie | |
| 1995 | Toby Wooldridge | |
| 1994 | Martin Thompson | |
| 1993 | Toby Wooldridge | |
| 1992 | Mike Davies | |
| 1991 | D. & K. Rowlatt | |
| 1990 | A. Robbins | |
| 1989 | R. Langley | |
| 1988 | C. Marley & P.Crocker | |
| 1987 | G. Carter | |
| 1986 | S. Adams |