| 1595 | 1973 | Ewa | Kmiecik | F | 1238 | 41 | 238 | F4049 | Stratford | CT | | 53:17.0 | 52:39.3 | 16:57 |
| 3113 | 1974 | Beata | Tokarski | F | 1239 | 49 | 239 | F4049 | Stratford | CT | | 53:17.4 | 52:39.5 | 16:57 |
| 2461 | 1975 | Elizabeth | Pinto | F | 1240 | 18 | 99 | F1418 | Stratford | CT | WILCOXSON ELEMENTARY SCHOOL | 54:58.4 | 52:39.6 | 16:57 |
| 2460 | 1976 | Christopher | Pinto | M | 731 | 50 | 107 | M5059 | Stratford | CT | WILCOXSON ELEMENTARY SCHOOL | 54:58.4 | 52:39.6 | 16:57 |
| 2780 | 1977 | Tom | Schachte | M | 732 | 67 | 48 | M6069 | New Canaan | CT | LONG LOTS SCHOOL | 58:00.9 | 52:40.0 | 16:58 |
| 122 | 1978 | Steven | Bacon | M | 733 | 50 | 108 | M5059 | Stratford | CT | | 56:11.1 | 52:47.3 | 17:00 |
| 550 | 1979 | Missy | Cole | F | 1241 | 61 | 58 | F6069 | Monroe | CT | | 57:13.6 | 52:53.7 | 17:02 |
| 2854 | 1980 | Diane | Sheehan | F | 1242 | 56 | 177 | F5059 | Trumbull | CT | | 56:08.0 | 52:57.1 | 17:03 |
| 1399 | 1981 | Eileen | Homza | F | 1243 | 57 | 178 | F5059 | Stratford | CT | | 55:54.6 | 52:57.5 | 17:03 |
| 3032 | 1982 | Katie | Sullivan | F | 1244 | 30 | 274 | F3039 | Stratford | CT | | 55:14.8 | 52:57.7 | 17:03 |
| 384 | 1983 | Kristi | Buynak | F | 1245 | 57 | 179 | F5059 | Shelton | CT | THE BICKERSONS | 55:15.0 | 52:58.4 | 17:04 |
| 1201 | 1984 | Ashley | Gomes | F | 1246 | 30 | 275 | F3039 | Stratford | CT | RUM RUNNERS | 54:38.6 | 52:59.0 | 17:04 |
| 36 | 1985 | Cindy | Allinson | F | 1247 | 59 | 180 | F5059 | Fairfield | CT | | 56:10.1 | 52:59.0 | 17:04 |
| 815 | 1986 | Timothy | Donaher | M | 734 | 66 | 49 | M6069 | Stratford | CT | DONAHER FAMILY | 58:18.5 | 53:02.6 | 17:05 |
| 927 | 1987 | Brittany | Everetts | F | 1248 | 27 | 259 | F1929 | Stratford | CT | | 56:58.3 | 53:03.2 | 17:05 |
| 1369 | 1988 | Lorraine | Hillgen-Santa | F | 1249 | 11 | 117 | F1013 | Stratford | CT | | 55:06.8 | 53:04.5 | 17:05 |
| 929 | 1989 | Emily | Everetts | F | 1250 | 24 | 260 | F1929 | Stratford | CT | | 56:59.5 | 53:05.8 | 17:06 |
| 605 | 1990 | Marianne | Cox | F | 1251 | 66 | 59 | F6069 | Stratford | CT | | 57:57.0 | 53:06.7 | 17:06 |
| 928 | 1991 | Carrie | Everetts | F | 1252 | 57 | 181 | F5059 | Stratford | CT | | 57:03.1 | 53:08.7 | 17:07 |
| 843 | 1992 | Karen | Dreger | F | 1253 | 38 | 276 | F3039 | Southbury | CT | | 55:45.8 | 53:10.4 | 17:07 |
| 3270 | 1993 | Sara | Washicko | F | 1254 | 58 | 182 | F5059 | Southbury | CT | | 55:45.8 | 53:10.4 | 17:07 |
| 799 | 1994 | Michael | Ditoro | M | 735 | 54 | 109 | M5059 | Shelton | CT | | 55:54.2 | 53:13.1 | 17:08 |
| 1490 | 1995 | Carol | Johnson | F | 1255 | 53 | 183 | F5059 | Derby | CT | | 55:54.3 | 53:13.3 | 17:08 |
| 490 | 1996 | Olivia | Chamberland | F | 1256 | 25 | 261 | F1929 | Shelton | CT | | 58:41.5 | 53:13.8 | 17:08 |
| 1404 | 1997 | Karrie | Hopkins | F | 1257 | 36 | 277 | F3039 | Meriden | CT | EDUCATORS HONORING VICKI | 57:24.4 | 53:13.9 | 17:08 |
| 2807 | 1998 | Stuart | Schwartz | M | 736 | 55 | 110 | M5059 | Trumbull | CT | | 57:22.6 | 53:14.7 | 17:09 |
| 3060 | 1999 | Thomas | EdwarTarczali | M | 737 | 61 | 50 | M6069 | Stratford | CT | | 57:21.7 | 53:14.8 | 17:09 |
| 1695 | 2000 | Brian | Larson | M | 738 | 34 | 139 | M3039 | Shelton | CT | | 58:40.9 | 53:15.1 | 17:09 |
| 1741 | 2001 | Cory | Leonard | M | 739 | 33 | 140 | M3039 | Oxford | CT | HEART AND SOLE | 54:28.2 | 53:18.8 | 17:10 |
| 197 | 2002 | Jamey | Benedetto | M | 740 | 34 | 141 | M3039 | Oxford | CT | HEART AND SOLE | 54:28.1 | 53:19.2 | 17:10 |
| 11 | 2003 | Liz | Adebiyi | F | 1258 | 52 | 184 | F5059 | Stratford | CT | | 59:24.9 | 53:23.6 | 17:12 |
| 1421 | 2004 | Erin | Hoyt | F | 1259 | 38 | 278 | F3039 | Trumbull | CT | | 57:25.7 | 53:24.7 | 17:12 |
| 1160 | 2005 | Melissa | Giandurco | F | 1260 | 38 | 279 | F3039 | Norwalk | CT | WOLFPIT | 57:26.4 | 53:25.0 | 17:12 |
| 1745 | 2006 | Audrey | Lesko | F | 1261 | 11 | 118 | F1013 | Monroe | CT | | 57:58.3 | 53:25.9 | 17:12 |
| 1457 | 2007 | Bruce | Jackson | M | 741 | 55 | 111 | M5059 | Shelton | CT | JACKSON LAW | 55:24.3 | 53:28.0 | 17:13 |
| 3096 | 2008 | Corey | Thompson | M | 742 | 23 | 115 | M1929 | Bridgeport | CT | TEAM KOSKOFF | 56:47.2 | 53:29.7 | 17:14 |
| 1283 | 2009 | Lorena | Gullotta | F | 1262 | 25 | 262 | F1929 | Bridgeport | CT | TEAM KOSKOFF | 56:47.2 | 53:30.4 | 17:14 |
| 1584 | 2010 | Dawn | Kindle | F | 1263 | 12 | 119 | F1013 | Shelton | CT | LORDSHIP COMMUNITY CHURCH | 57:51.3 | 53:36.4 | 17:16 |
| 2842 | 2011 | Gabrielle | Shannon | F | 1264 | 17 | 100 | F1418 | Stratford | CT | | 56:41.6 | 53:36.7 | 17:16 |
| 2839 | 2012 | Brooke | Shannon | F | 1265 | 18 | 101 | F1418 | Stratford | CT | | 56:41.7 | 53:37.3 | 17:16 |
| 3041 | 2013 | Ana | Svetz | F | 1266 | 27 | 263 | F1929 | Derby | CT | ANSONIA PUBLIC SCHOOLS | 57:39.6 | 53:39.6 | 17:17 |
| 2177 | 2014 | Carrie | Negron | F | 1267 | 39 | 280 | F3039 | Stratford | CT | | 57:51.7 | 53:39.7 | 17:17 |
| 3307 | 2015 | Beth | Whamond | F | 1268 | 48 | 240 | F4049 | Newtown | CT | JACKSON LAW | 55:27.3 | 53:39.8 | 17:17 |
| 2950 | 2016 | Samdi | Soltis | F | 1269 | 50 | 185 | F5059 | Seymour | CT | JACKSON LAW | 55:27.4 | 53:40.6 | 17:17 |
| 1368 | 2017 | Jennifer | Hillgen-Santa | F | 1270 | 44 | 241 | F4049 | Stratford | CT | | 55:43.2 | 53:40.9 | 17:17 |
| 628 | 2018 | Meredith | Curina | F | 1271 | 41 | 242 | F4049 | Ansonia | CT | ANSONIA PUBLIC SCHOOLS | 57:39.5 | 53:41.9 | 17:17 |
| 816 | 2019 | Maurine | Donahue | F | 1272 | 47 | 243 | F4049 | New Haven | CT | ANSONIA PUBLIC SCHOOLS | 57:39.9 | 53:42.0 | 17:18 |
| 72 | 2020 | Saikumar | Annavajjhala | M | 743 | 50 | 112 | M5059 | Stratford | CT | | 57:46.9 | 53:43.0 | 17:18 |
| 2783 | 2021 | Jaqi | Scheck | F | 1273 | 50 | 186 | F5059 | Orange | CT | JACKSON LAW | 55:30.2 | 53:43.1 | 17:18 |
| 716 | 2022 | Pamela | Delbene | F | 1274 | 60 | 60 | F6069 | Stratford | CT | | 59:17.0 | 53:43.6 | 17:18 |
| 1771 | 2023 | Nicole | Lisanti | F | 1275 | 40 | 244 | F4049 | Monroe | CT | | 58:30.8 | 53:44.8 | 17:18 |
| 2235 | 2024 | Rebecca | ODonnell | F | 1276 | 38 | 281 | F3039 | Monroe | CT | | 58:30.7 | 53:45.2 | 17:19 |
| 1531 | 2025 | Linda | Kangro | F | 1277 | 30 | 282 | F3039 | Shelton | CT | WESTPORT PUBLIC SCHOOLS | 57:35.7 | 53:47.8 | 17:19 |
| 125 | 2026 | Sue | Baillargeon | F | 1278 | 46 | 245 | F4049 | Shelton | CT | JACKSON LAW | 55:30.5 | 53:48.0 | 17:19 |
| 2922 | 2027 | Cynthia | Smith | F | 1279 | 61 | 61 | F6069 | Stratford | CT | STRATFORD LIBRARY | 55:14.1 | 53:48.3 | 17:20 |
| 679 | 2028 | Jayne | DeGant | F | 1280 | 61 | 62 | F6069 | Stratford | CT | | 55:13.9 | 53:48.5 | 17:20 |
| 1503 | 2029 | Robin | Jones | F | 1281 | 60 | 63 | F6069 | Fairfield | CT | FAIRFIELD POLICE DEPARTMENT | 56:23.0 | 53:50.1 | 17:20 |
| 462 | 2030 | Gale | Caruso | F | 1282 | 57 | 187 | F5059 | Fairfield | CT | FAIRFIELD POLICE DEPARTMENT | 56:23.1 | 53:50.2 | 17:20 |
| 1549 | 2031 | Aidan | Kelemen | M | 744 | 10 | 73 | M1013 | Stratford | CT | | 57:29.2 | 53:50.4 | 17:20 |
| 1370 | 2032 | Michael | Hillgen-Santa | M | 745 | 49 | 140 | M4049 | Stratford | CT | | 55:53.0 | 53:50.6 | 17:20 |
| 1912 | 2033 | Madisyn | Markland | F | 1283 | 8 | 19 | F-9 | Stratford | CT | ST MARK SCHOOL | 58:33.6 | 53:51.4 | 17:21 |
| 1106 | 2034 | Leigh | Gabriel | F | 1284 | 36 | 283 | F3039 | Stratford | CT | | 58:26.8 | 53:53.0 | 17:21 |
| 2655 | 2035 | Pamela | Rogalin | F | 1285 | 58 | 188 | F5059 | Shelton | CT | | 58:26.6 | 53:54.0 | 17:21 |
| 680 | 2036 | John | DeGant | M | 746 | 67 | 51 | M6069 | Stratford | CT | | 55:21.0 | 53:55.2 | 17:22 |
| 2290 | 2037 | Denise | Ortiz | F | 1286 | 54 | 189 | F5059 | Stratford | CT | ORTIZ FAMILY | 54:35.7 | 53:55.4 | 17:22 |
| 2291 | 2038 | Eduardo | Ortiz | M | 747 | 59 | 113 | M5059 | Stratford | CT | ORTIZ FAMILY | 54:35.9 | 53:55.9 | 17:22 |
| 2923 | 2039 | Daniel | Smith | M | 748 | 64 | 52 | M6069 | Stratford | CT | STRATFORD LIBRARY | 55:20.8 | 53:56.5 | 17:22 |
| 3082 | 2040 | Sherri | Tessitore | F | 1287 | 47 | 246 | F4049 | Orange | CT | | 57:05.1 | 53:56.9 | 17:22 |
| 1809 | 2041 | Kathleen | Lovanio | F | 1288 | 68 | 64 | F6069 | Orange | CT | | 57:05.3 | 53:57.4 | 17:22 |
| 2557 | 2042 | Maritza | Ramirez | F | 1289 | 53 | 190 | F5059 | Stratford | CT | | 54:37.4 | 53:58.3 | 17:23 |
| 2556 | 2043 | Joyce | Ramirez | F | 1290 | 55 | 191 | F5059 | New York | NY | | 54:37.6 | 53:58.5 | 17:23 |
| 772 | 2044 | John | Dickinson | M | 749 | 41 | 141 | M4049 | Danbury | CT | | 1:06:03.6 | 54:01.7 | 17:24 |
| 3015 | 2045 | Scarlet | Strakova | F | 1291 | 41 | 247 | F4049 | Danbury | CT | | 1:06:03.9 | 54:01.8 | 17:24 |
| 1698 | 2046 | Kristin | Larson | F | 1292 | 44 | 248 | F4049 | Sandy Hook | CT | | 58:34.8 | 54:03.1 | 17:24 |
| 1787 | 2047 | Ken | Loerzel | M | 750 | 68 | 53 | M6069 | Sandy Hook | CT | | 58:34.6 | 54:03.3 | 17:24 |
| 3325 | 2048 | Aneequa | Williams | F | 1293 | 28 | 264 | F1929 | Stratford | CT | STRATFORD ORTHODONTICS / CT BRAC | 56:22.9 | 54:03.7 | 17:25 |
| 2611 | 2049 | Jennifer | Rivera | F | 1294 | 36 | 284 | F3039 | Bridgeport | CT | STRATFORD ORTHODONTICS/CT BRACES | 56:24.2 | 54:05.3 | 17:25 |
| 2084 | 2050 | Nicole | Morales | F | 1295 | 30 | 285 | F3039 | Bridgeport | CT | STRATFORD ORTHODONTICS/ CT BRACE | 56:24.5 | 54:05.5 | 17:25 |
| 1957 | 2051 | Jeanine | May | F | 1296 | 49 | 249 | F4049 | Stratford | CT | ST MARK SCHOOL | 58:59.6 | 54:09.7 | 17:26 |
| 1700 | 2052 | Sarah | Larson | F | 1297 | 34 | 286 | F3039 | Shelton | CT | | 59:35.9 | 54:09.9 | 17:27 |
| 1830 | 2053 | Debbie | Lyman | F | 1298 | 54 | 192 | F5059 | Stratford | CT | | 54:52.0 | 54:10.9 | 17:27 |
| 993 | 2054 | Jason | Fenstermaker | M | 751 | 43 | 142 | M4049 | Seymour | CT | PERRY HILL SCHOOL | 58:54.7 | 54:15.3 | 17:28 |
| 1852 | 2055 | Shannon | MacOnochie | F | 1299 | 11 | 120 | F1013 | Stratford | CT | ST MARK SCHOOL | 58:59.8 | 54:16.9 | 17:29 |
| 483 | 2056 | Lauren | Cederbaum | F | 1300 | 23 | 265 | F1929 | Trumbull | CT | | 57:09.0 | 54:17.2 | 17:29 |
| 1747 | 2057 | Julee | Lesko | F | 1301 | 46 | 250 | F4049 | Monroe | CT | | 58:51.7 | 54:18.7 | 17:29 |
| 2979 | 2058 | Anthony | Sposta | M | 752 | 18 | 89 | M1418 | Stratford | CT | | 54:53.5 | 54:21.3 | 17:30 |
| 92 | 2059 | Jaileen | Artiaga | F | 1302 | 17 | 102 | F1418 | Stratford | CT | | 54:53.6 | 54:21.6 | 17:30 |
| 2452 | 2060 | Norine | Pigliucci | F | 1303 | 43 | 251 | F4049 | Shelton | CT | ST MARK SCHOOL | 57:24.4 | 54:22.1 | 17:30 |
| 2379 | 2061 | Joann | Pavia | F | 1304 | 63 | 65 | F6069 | Stratford | CT | LLJ INC | 56:26.1 | 54:22.4 | 17:31 |
| 2454 | 2062 | Peter | Pigliucci | M | 753 | 12 | 74 | M1013 | Shelton | CT | ST MARK SCHOOL | 57:24.4 | 54:22.8 | 17:31 |
| 2038 | 2063 | Cheryl | Miller | F | 1305 | 58 | 193 | F5059 | Fairfield | CT | FAIRFIELD POLICE DEPARTMENT | 56:56.6 | 54:23.7 | 17:31 |
| 3179 | 2064 | Cecilia | Urbanowicz | F | 1306 | 57 | 194 | F5059 | Milford | CT | BERCHEM MOSES P.C. | 58:28.3 | 54:24.0 | 17:31 |
| 2607 | 2065 | Breana | Rivera | F | 1307 | 23 | 266 | F1929 | Bridgeport | CT | | 59:53.1 | 54:25.0 | 17:31 |
| 638 | 2066 | Karen | Dabolli | F | 1308 | 57 | 195 | F5059 | Milford | CT | BERCHEM MOSES P.C. | 58:28.6 | 54:25.2 | 17:31 |
| 61 | 2067 | Megan | Anderson | F | 1309 | 45 | 252 | F4049 | Trumbull | CT | | 59:39.9 | 54:26.7 | 17:32 |
| 2760 | 2068 | Sandra | Sarmiento | F | 1310 | 57 | 196 | F5059 | Stratford | CT | STRATFORD ANGELS | 56:38.5 | 54:27.0 | 17:32 |
| 911 | 2069 | Ellie | Eng | F | 1311 | 65 | 66 | F6069 | Stratford | CT | STRATFORD ANGELS | 56:39.2 | 54:27.1 | 17:32 |
| 1678 | 2070 | Lindsey | Lalli | F | 1312 | 11 | 121 | F1013 | Trumbull | CT | | 55:55.5 | 54:27.3 | 17:32 |
| 1174 | 2071 | Giovanna | Gill | F | 1313 | 41 | 253 | F4049 | Stratford | CT | ELI WHITNEY ELEMENTARY SCHOOL | 1:00:33.7 | 54:28.4 | 17:32 |
| 1614 | 2072 | Maeve | Korchinski | F | 1314 | 9 | 20 | F-9 | Trumbull | CT | | 55:56.0 | 54:28.7 | 17:33 |