Milton, MA
| Rank | Year | Name | Category | Time |
|---|---|---|---|---|
| 1 | 2017 | Matt Picard | M 30-39 | 4:45:00 |
| 2 | 2017 | Josh Katzman | M 30-39 | 4:45:00 |
| 3 | 2012 | Josh Katzman | M 30-39 | 4:49:00 |
| 4 | 2012 | Scott Traer | M 30-39 | 4:49:00 |
| 5 | 2013 | Josh Katzman | M 30-39 | 4:54:00 |
| 6 | 2010 | Josh Katzman | M 30-39 | 4:56:00 |
| 7 | 2019 | Matt Picard | M 30-39 | 5:04:00 |
| 8 | 2013 | Anthony Parillo | M 20-29 | 5:08:00 |
| 9 | 2009 | Josh Katzman | M 20-29 | 5:16:00 |
| 10 | 2009 | Garry Harrington | M 40-49 | 5:16:00 |
| 11 | 2013 | Jack Bailey | M 30-39 | 5:17:00 |
| 12 | 2013 | Christopher Cappellini | M 40-49 | 5:18:00 |
| 13 | 2013 | Tim Finocchio | M 30-39 | 5:19:00 |
| 14 | 2017 | Tim Finocchio | M 30-39 | 5:26:00 |
| 15 | 2019 | Kyle Bergemann | M 20-29 | 5:28:00 |
| 16 | 2012 | Christopher Cappellini | M 40-49 | 5:30:00 |
| 17 | 2016 | Josh Katzman | M 30-39 | 5:30:00 |
| 18 | 2012 | Tim Finocchio | M 30-39 | 5:31:00 |
| 19 | 2012 | Mark Blakeley | M 40-49 | 5:32:00 |
| 20 | 2015 | Ben Eysenbach | M 20-29 | 5:36:00 |
| 21 | 2018 | Tim Finocchio | M 40-49 | 5:36:00 |
| 22 | 2023 | Wilson Ray | M 20-29 | 5:38:00 |
| 23 | 2014 | Ron Moore | M 40-49 | 5:38:00 |
| 24 | 2000 | Stephen Pero | M 40-49 | 5:38:00 |
| 25 | 2013 | Garry Harrington | M 50-59 | 5:45:00 |
| 26 | 1999 | Peter Palmer | M 40-49 | 5:47:00 |
| 27 | 2004 | Wesley Finnemore | M 40-49 | 5:48:00 |
| 28 | 2017 | Kyle Bergemann | M 20-29 | 5:48:00 |
| 29 | 1999 | Hans Put | M 30-39 | 5:51:00 |
| 30 | 2010 | Jeff List | M 50-59 | 5:52:00 |
| 31 | 2010 | Jeff Vogel | M 30-39 | 5:52:00 |
| 32 | 2017 | Elise Deroo | F 20-29 | 5:53:00 |
| 33 | 2005 | Craig Wilson | M 50-59 | 5:54:00 |
| 34 | 2022 | Laura Ricci | F 30-39 | 5:55:00 |
| 35 | 1999 | Stephen Pero | M 40-49 | 5:56:00 |
| 36 | 2022 | Joshua Cave | M 30-39 | 5:57:00 |
| 37 | 2022 | Jacob Varekamp | M 40-49 | 5:57:00 |
| 38 | 2004 | Thomas Mikkelsen | M 30-39 | 5:58:00 |
| 39 | 2011 | Tim Finocchio | M 30-39 | 5:58:00 |
| 40 | 2021 | Jeff Beling | M 30-39 | 6:01:00 |
| 41 | 2021 | Jacob Varekamp | M 40-49 | 6:01:00 |
| 42 | 2016 | Kehr Davis | F 30-39 | 6:02:00 |
| 43 | 2016 | Kristina Folcik | F 30-39 | 6:02:00 |
| 44 | 2016 | Jack Pilla | M 50-59 | 6:02:00 |
| 45 | 2023 | Toby Harding | M 20-29 | 6:04:00 |
| 46 | 2008 | Robert Mathes | M 50-59 | 6:04:00 |
| 47 | 2002 | Stephen Pero | M 50-59 | 6:04:00 |
| 48 | 2010 | Paul Funch | M 60-69 | 6:06:00 |
| 49 | 2010 | Bogie Dumitrescu | M 30-39 | 6:06:00 |
| 50 | 2010 | Stephen Pero | M 50-59 | 6:06:00 |
| 51 | 2013 | Jeff List | M 50-59 | 6:06:00 |
| 52 | 2012 | Robert Mathes | M 60-69 | 6:07:00 |
| 53 | 2012 | Giles Gregory | M 40-49 | 6:07:00 |
| 54 | 2012 | Howard Breinan | M 40-49 | 6:07:00 |
| 55 | 2009 | Howard Breinan | M 40-49 | 6:08:00 |
| 56 | 2009 | Chris Taft | M 20-29 | 6:08:00 |
| 57 | 2018 | Anonymous Runner | F 20-29 | 6:08:00 |
| 58 | 2018 | Justin Hetherington | M 30-39 | 6:08:00 |
| 59 | 2023 | Jason Kaplan | M 40-49 | 6:09:00 |
| 60 | 2023 | Eli Converse | M 20-29 | 6:09:00 |
| 61 | 2019 | Ryan Williams | M 30-39 | 6:09:00 |
| 62 | 2013 | David Loutzenheiser | M 40-49 | 6:09:00 |
| 63 | 2004 | Christopher Haley | M 40-49 | 6:09:00 |
| 64 | 2000 | Peter Palmer | M 40-49 | 6:09:00 |
| 65 | 2000 | Hans Put | M 40-49 | 6:09:00 |
| 66 | 2016 | Jeff List | M 50-59 | 6:10:00 |
| 67 | 2007 | Garry Harrington | M 40-49 | 6:10:00 |
| 68 | 1998 | Peter Palmer | M 40-49 | 6:10:00 |
| 69 | 2014 | Ben Eysenbach | M < 20 | 6:10:00 |
| 70 | 2000 | Guido Medeiros | M | 6:11:00 |
| 71 | 2000 | Sue Johnston | F 30-39 | 6:11:00 |
| 72 | 2022 | Brenner Burkholder | M 20-29 | 6:12:00 |
| 73 | 2019 | Victor Zuniga | M 40-49 | 6:12:00 |
| 74 | 2019 | Katelyn Tocci | F 30-39 | 6:12:00 |
| 75 | 2012 | Jeff List | M 50-59 | 6:13:00 |
| 76 | 2013 | Silas Fitzgerald | M 30-39 | 6:15:00 |
| 77 | 2007 | Robert Mathes | M 50-59 | 6:15:00 |
| 78 | 2009 | Stephen Pero | M 50-59 | 6:16:00 |
| 79 | 2010 | Mike Camarillo | M | 6:18:00 |
| 80 | 2021 | Laura Ricci | F 30-39 | 6:19:00 |
| 81 | 2015 | Harold Eyster | M 20-29 | 6:19:00 |
| 82 | 2010 | Mark Buongiorno | M 40-49 | 6:20:00 |
| 83 | 2010 | Howard Breinan | M 40-49 | 6:20:00 |
| 84 | 2021 | Adam Wilcox | M 30-39 | 6:20:00 |
| 85 | 2008 | Paul Kearney | M 20-29 | 6:21:00 |
| 86 | 2015 | Anthony Parillo | M 30-39 | 6:22:00 |
| 87 | 2015 | Michael McDuffie | M 30-39 | 6:22:00 |
| 88 | 1999 | Sue Johnston | F 30-39 | 6:22:00 |
| 89 | 1998 | Dave Ackerman | M 30-39 | 6:22:00 |
| 90 | 1998 | Christopher Haley | M 40-49 | 6:22:00 |
| 91 | 2004 | Stephen Pero | M 50-59 | 6:23:00 |
| 92 | 2014 | Anthony Parillo | M 20-29 | 6:23:00 |
| 93 | 2005 | Richard Collins | M 40-49 | 6:26:00 |
| 94 | 2008 | Jeff List | M 40-49 | 6:26:00 |
| 95 | 2005 | Stephen Pero | M 50-59 | 6:26:00 |
| 96 | 2019 | Max Dismukes | M 20-29 | 6:27:00 |
| 97 | 2018 | Brian Huffman | M 30-39 | 6:27:00 |
| 98 | 1997 | Daniel Purdy | M 30-39 | 6:27:00 |
| 99 | 1997 | Christopher Haley | M 40-49 | 6:27:00 |
| 100 | 1997 | Stephen Pero | M 40-49 | 6:27:00 |
