| 1075 | 20 | Lai | Sun | M | Cervalis/CyrusOne | 21:59.6 | 22:33.8 | 7:16 |
| 1063 | 21 | Samuel | Bowlby | M | Bridgewater Associates | 22:36.2 | 22:40.0 | 7:18 |
| 1218 | 22 | Spenser | Christensen | M | Sun Products | 22:30.3 | 22:47.0 | 7:20 |
| 1283 | 23 | Karina | OFriel | F | Reed Exhibitions | 22:51.1 | 22:51.8 | 7:22 |
| 1208 | 24 | Hollin | Abraham | F | Sun Products | 22:45.3 | 22:56.1 | 7:23 |
| 1230 | 25 | Yibo | He | M | Tauck World Discovery | 23:01.3 | 23:03.8 | 7:26 |
| 1216 | 26 | Max | Branstetter | M | Sun Products | 22:55.5 | 23:11.0 | 7:28 |
| 1251 | 27 | Tony | Menchaca | M | Verde Energy USA | 23:13.4 | 23:17.3 | 7:30 |
| 1160 | 28 | Tom | MacDonald | M | MBI Inc. | 23:22.0 | 23:33.6 | 7:35 |
| 1062 | 29 | Sam | Cooke | M | Bridgewater Associates | 23:33.8 | 23:37.5 | 7:37 |
| 1041 | 30 | Jason | Corsi | M | Bridgeport YMCA | 23:38.6 | 23:42.8 | 7:38 |
| 1090 | 31 | Fred | Eshraghi | M | City of Norwalk | 23:45.8 | 23:47.8 | 7:40 |
| 1186 | 32 | Marc | Simon | M | Reed Exhibitions | 23:42.4 | 23:48.0 | 7:40 |
| 1240 | 33 | Sarah | Kehoe | F | The LaurelRock Company | 23:51.5 | 23:51.5 | 7:41 |
| 1149 | 34 | Brent | Edwards | M | MBI Inc. | 23:30.9 | 23:52.3 | 7:41 |
| 1136 | 35 | Colin | Ennis | M | GE Corporate Headquarters | 23:50.6 | 24:01.0 | 7:44 |
| 1098 | 36 | Dina | Nathanson | F | Cohen and Wolf P.C. | 23:36.0 | 24:01.0 | 7:44 |
| 1125 | 37 | Thomas | Jordan | M | Datto | 24:01.1 | 24:01.2 | 7:44 |
| 1044 | 38 | Alex | Capozzoli | M | Bridgewater Associates | 23:48.9 | 24:03.1 | 7:45 |
| 1101 | 39 | Phil | Pires | M | Cohen and Wolf P.C. | 23:49.5 | 24:05.1 | 7:46 |
| 1118 | 40 | Luis | Ayala | M | Datto | 24:03.8 | 24:07.9 | 7:47 |
| 1254 | 41 | Don | ONeil | M | Datto | 24:05.3 | 24:10.5 | 7:47 |
| 1173 | 42 | Mary | McCarthy | F | Millward Brown | 24:08.1 | 24:16.5 | 7:49 |
| 1167 | 43 | Brian | Singer | M | Millward Brown | 24:08.3 | 24:17.7 | 7:50 |
| 1239 | 44 | Peter | Kehoe | M | The LaurelRock Company | 24:05.3 | 24:21.4 | 7:51 |
| 1035 | 45 | Alexander | Fornaciari | M | Better Homes Construction | 24:28.9 | 24:28.9 | 7:53 |
| 1278 | 46 | Del | Toreno | M | | 24:26.0 | 24:29.3 | 7:53 |
| 1071 | 47 | Bob | Crespi | M | Cervalis/CyrusOne | 23:57.0 | 24:32.9 | 7:55 |
| 1227 | 48 | Orlando | Sanchez | M | Tauck World Discovery | 24:30.2 | 24:33.2 | 7:55 |
| 1099 | 49 | Geraldine | Pires | F | Cohen and Wolf P.C. | 24:10.6 | 24:34.1 | 7:55 |
| 1215 | 50 | Lauriston | Beech | M | Sun Products | 24:32.4 | 24:48.6 | 8:00 |
| 1289 | 51 | Gail | Heffron | F | Sacred Heart University | 24:39.8 | 24:49.7 | 8:00 |
| 1261 | 52 | Emma | Demarche | F | The LaurelRock Company | 24:35.6 | 24:56.7 | 8:02 |
| 1126 | 53 | James | Carlon | M | Day Pitney | 24:38.3 | 25:01.4 | 8:04 |
| 1111 | 54 | Mollie | Royer | F | Darien Library | 24:39.9 | 25:02.8 | 8:04 |
| 1286 | 55 | Shaun | Gagnon | M | Tooher-Ferraris Insurance Group | 24:44.6 | 25:04.0 | 8:05 |
| 1217 | 56 | Scott | Smith | M | Sun Products | 24:50.4 | 25:05.8 | 8:05 |
| 1197 | 57 | James | Carl | M | Sacred Heart University | 24:55.9 | 25:05.9 | 8:05 |
| 1214 | 58 | Lamarr | Shand | M | Sun Products | 24:53.6 | 25:08.4 | 8:06 |
| 1156 | 59 | Mike | Wilbur | M | MBI Inc. | 24:56.8 | 25:08.7 | 8:06 |
| 1108 | 60 | Lisa | Nowlain | F | Darien Library | 24:46.9 | 25:09.5 | 8:06 |
| 1114 | 61 | Brendan | Patton | M | Datto | 25:07.8 | 25:12.6 | 8:07 |
| 1104 | 62 | Stuart | Katz | M | Cohen and Wolf P.C. | 24:55.6 | 25:16.1 | 8:08 |
| 1281 | 63 | Katie | Spiker | F | | 25:18.1 | 25:19.4 | 8:10 |
| 1233 | 64 | Gerard | Duffy | M | The Adventure Park at the Discovery Museum | 25:20.2 | 25:20.2 | 8:10 |
| 1045 | 65 | Alexander | Pimentel | M | Bridgewater Associates | 25:05.9 | 25:22.8 | 8:11 |
| 1171 | 66 | Karen | Coffey | F | Millward Brown | 25:20.5 | 25:29.8 | 8:13 |
| 1038 | 67 | Tom | Landry | M | Better Homes Construction | 25:37.7 | 25:37.7 | 8:15 |
| 1280 | 68 | Laurie | Humphrey | F | Tauck World Discovery | 25:36.4 | 25:38.3 | 8:16 |
| 1275 | 69 | John | Cappelli | M | Tauck World Discovery | 25:41.2 | 25:43.0 | 8:17 |
| 1276 | 70 | Barend | Wiegman | M | GE Corporate Headquarters | 25:36.0 | 25:46.6 | 8:18 |
| 1039 | 71 | Zachary | Fornaciari | M | Better Homes Construction | 25:44.6 | 25:48.3 | 8:19 |
| 1213 | 72 | Ken | Krasnow | M | Sun Products | 25:35.6 | 25:50.6 | 8:20 |
| 1132 | 73 | Ryan | Tougias | M | Day Pitney | 25:20.3 | 25:53.5 | 8:21 |
| 1270 | 74 | Niki | Razali | M | ASML | 25:56.8 | 25:56.9 | 8:22 |
| 1102 | 75 | Robyn | Drucker | F | Cohen and Wolf P.C. | 25:33.9 | 25:57.5 | 8:22 |
| 1172 | 76 | Lea | Cervone | F | Millward Brown | 25:48.5 | 25:57.5 | 8:22 |
| 1139 | 77 | Michael | Gnibus | M | GE Corporate Headquarters | 25:56.3 | 26:08.6 | 8:25 |
| 1131 | 78 | Matt | Smith | M | Day Pitney | 25:48.1 | 26:09.9 | 8:26 |
| 1200 | 79 | Michael | Ward | M | Sacred Heart University | 26:06.1 | 26:13.7 | 8:27 |
| 1158 | 80 | Sheri | St. John | F | MBI Inc. | 26:12.2 | 26:19.3 | 8:29 |
| 1262 | 81 | Kym | OKeefe | F | Forstone Capital | 26:20.4 | 26:23.5 | 8:30 |
| 1232 | 82 | Ceili | Grinnell | F | The Adventure Park at the Discovery Museum | 26:26.5 | 26:26.5 | 8:31 |
| 1042 | 83 | Pam | Hearn | F | Bridgeport YMCA | 26:24.3 | 26:28.8 | 8:32 |
| 1196 | 84 | Frank | Novak | M | Sacred Heart University | 26:23.1 | 26:32.2 | 8:33 |
| 1124 | 85 | Steve | Hewitt | M | Datto | 26:34.7 | 26:39.6 | 8:35 |
| 1121 | 86 | Michelle | McComb | F | Datto | 26:36.1 | 26:41.3 | 8:36 |
| 1247 | 87 | Renee | Clifford | F | Verde Energy USA | 26:39.4 | 26:41.8 | 8:36 |
| 1292 | 88 | Pedro | Yupa | M | | 26:46.6 | 26:46.7 | 8:38 |
| 1065 | 89 | Tom | Allbee | M | Bridgewater Associates | 26:46.5 | 26:50.9 | 8:39 |
| 1052 | 90 | Jeff | Frechette | M | Bridgewater Associates | 26:29.8 | 26:52.8 | 8:40 |
| 1169 | 91 | Ian | Elmer | M | Millward Brown | 26:53.4 | 27:04.3 | 8:43 |
| 1162 | 92 | Wendy | Bonanni | F | MBI Inc. | 27:03.4 | 27:09.8 | 8:45 |
| 1168 | 93 | David | Sesay | M | Millward Brown | 27:05.2 | 27:12.8 | 8:46 |
| 1296 | 94 | David | Coates | M | New Canaan Library | 26:40.7 | 27:12.9 | 8:46 |
| 1130 | 95 | Maria | Woehr | F | Day Pitney | 26:36.4 | 27:13.4 | 8:46 |
| 1034 | 96 | Wendy | Lynch | F | Berkshire Hathaway Home Services New England | 26:38.1 | 27:14.0 | 8:46 |
| 1188 | 97 | Mark | Depanfilis | M | Reed Exhibitions | 27:04.7 | 27:14.4 | 8:47 |
| 1151 | 98 | Jeff | Robison | M | MBI Inc. | 26:56.9 | 27:16.0 | 8:47 |
| 1295 | 99 | Rocco | Palmieri | M | Datto | 27:12.0 | 27:18.9 | 8:48 |
| 1189 | 100 | Mary | Shaughnessy | F | Reed Exhibitions | 27:21.5 | 27:26.7 | 8:50 |
| 1201 | 101 | Sally | Schettino | F | Sacred Heart University | 27:26.8 | 27:35.7 | 8:53 |
| 1265 | 102 | Tom | Walsh | M | Brody Wilkinson PC | 27:04.9 | 27:39.0 | 8:54 |
| 1187 | 103 | Marie | Browne | F | Reed Exhibitions | 27:37.7 | 27:42.3 | 8:56 |
| 1117 | 104 | Kristen | Rydberg | F | Datto | 27:46.3 | 27:46.3 | 8:57 |
| 1212 | 105 | John | Chestnut | M | Sun Products | 27:45.7 | 28:04.2 | 9:03 |
| 1115 | 106 | Emily | Curtis | F | Datto | 27:57.1 | 28:06.0 | 9:03 |
| 1248 | 107 | Richard | Reilly | M | Verde Energy USA | 28:05.7 | 28:08.8 | 9:04 |
| 1157 | 108 | Russ | Friedman | M | MBI Inc. | 28:02.7 | 28:10.2 | 9:04 |
| 1100 | 109 | Lauren | Walters | F | Cohen and Wolf P.C. | 27:44.3 | 28:10.2 | 9:04 |
| 1031 | 110 | Josephine | Simko | F | Berkshire Hathaway Home Services New England | 28:16.6 | 28:29.4 | 9:11 |
| 1182 | 111 | Jorge | Carreno | M | Reed Exhibitions | 28:17.3 | 28:30.1 | 9:11 |
| 1236 | 112 | Tim | Cairns | M | The Adventure Park at the Discovery Museum | 28:30.9 | 28:32.0 | 9:12 |
| 1175 | 113 | Alexa | Roy | F | New Canaan Library | 28:07.8 | 28:40.7 | 9:14 |
| 1242 | 114 | Erin | Wandelt | F | Verde Energy USA | 28:35.2 | 28:45.8 | 9:16 |
| 1194 | 115 | Amy | Ricci | F | Sacred Heart University | 28:53.3 | 29:04.0 | 9:22 |
| 1287 | 116 | Michael | Koehler | M | Reed Exhibitions | 29:01.1 | 29:13.8 | 9:25 |
| 1206 | 117 | Maura | Loizzo | F | St Monicas | 29:08.8 | 29:14.9 | 9:25 |
| 1273 | 118 | Morgan | Hricay | F | | 28:31.4 | 29:15.2 | 9:25 |
| 1274 | 119 | Jim | Hricay | M | | 28:33.9 | 29:17.9 | 9:26 |