Named after the late Vermont State Senator, Edward Janeway, who also served on Stratton Mountain’s board of directors, the Janeway Cup is awarded to the fastest man and woman over the age of 40. This race has been a long-time favorite on the New England Masters circuit, dating back to at least 1970. A quick glance at the past winners of this perpetual trophy reads like a Who’s Who of masters ski racing.
| Year | Men | Women |
| 1999 | Bob Hill | Nadine Price |
| 2000 | Pepi Neubauer | Nadine Price |
| 2001 | Pepi Neubauer | Margaret Vaughn |
| 2002 | Doug Tucker | Lisa Densmore |
| 2003 | Scott Hardy | Sally White |
| 2004 | Patrick McNamara | Sally White |
| 2005 | ||
| 2006 | Scott Hardy | Nadine Price |
| 2007 | Scott Hardy | Nadine Price |
| 2008 | Bob Hill | Carolyn Beckedorff |
| 2009 | Bob Hill | Carolyn Beckedorff |
| 2010 | Patrick McNamara | Carolyn Beckedorff |
| 2011 | Patrick McNamara | Lisa Densmore |
| 2012 | Pepi Neubauer | Nadine Price |
| 2013 | Terence Fogarty | Cinthia Audet |
| 2014 | Patrick McNamara | Cinthia Audet |
| 2015 | Brian Irwin | Cinthia Audet |
| 2016 | Patrick McNamara | Polly Schmid |
| 2017 | Patrick McNamara | Sharon Way |
| 2019 | Mark George | Polly Schmid |
| 2020 | Mark Sertle | Polly Schmid |
| 2022 | Patrick McNamara | Kerry Finch |
| 2023 | Stephane Ricard | Kerry Finch |