The Joss Naylor Challenge is for those who are over 50 years old. The route leaves Pooley Bridge to traverse 30 summits over a distance of 48 miles and climbing 17,000 feet (77km, 5182m) with only two road crossings. The inaugural run from Pooley Bridge to Wasdale was made by Joss Naylor in 1990, at the age of 54. Contenders have to complete the course in a predetermined time which depends on their age. All contenders have to donate a minimum of £100 to a charity of their choice and those who are successful are awarded with a commemorative tankard at the annual dinner. The following is a list of those who have completed the challenge under the Club name
| Name | JNLC number | Age group | Date |
| Leo Pollard | 031 | M65 | 14-08-1999 |
| Chris Farrell | 052 | M60 | 09-07-2005 |
| Dave Makin | 131 | M50 | 21-04-2012 |
| Tash Fellowes | 218 | W50 | 09-09-2017 |
| Rob Green | 230 | M55 | 15-09-2018 |
| Chris Lloyd | M55 | 08-06-2019 |