| 179 | 247 | Thomas | Little | M | City of Norwalk | 28:40 | 28:55 | 9:19 |
| 765 | 248 | Amy | Harlacker | F | Commonfund | 28:42 | 29:00 | 9:20 |
| 183 | 249 | Amanda | Daher | F | Commonfund | 28:59 | 29:02 | 9:21 |
| 798 | 250 | Tory | Steinbag | M | New Canaan Library | 28:03 | 29:03 | 9:21 |
| 399 | 251 | Kelly | Agosti | F | IDOC LLC | 28:45 | 29:06 | 9:22 |
| 752 | 252 | Hannah | Wang | F | FactSet | 29:11 | 29:11 | 9:24 |
| 20 | 253 | David | Ferris | M | Antinozzi Associates | 28:11 | 29:12 | 9:24 |
| 19 | 254 | Brittney | Mayo | F | Antinozzi Associates | 28:14 | 29:12 | 9:24 |
| 586 | 255 | Laura | Boullianne | F | Reed Exhibitions | 28:27 | 29:13 | 9:25 |
| 594 | 256 | Donna | Ferenz | F | Reynolds + Rowella | 28:23 | 29:17 | 9:26 |
| 347 | 257 | Kevin | Perregaux | M | Foundation Source | 28:37 | 29:19 | 9:26 |
| 193 | 258 | Christina | Chao | F | Connecticut Dermatology Group | 28:53 | 29:20 | 9:27 |
| 234 | 259 | Aaron | Oommen | M | FactSet | 29:22 | 29:22 | 9:28 |
| 616 | 260 | Joseph | Nankof | M | Rocaton | 28:46 | 29:23 | 9:28 |
| 328 | 261 | Joe | Deering | M | First County Bank | 28:44 | 29:27 | 9:29 |
| 201 | 262 | Lisa | Sheehan | F | Connecticut Dermatology Group | 29:00 | 29:27 | 9:29 |
| 192 | 263 | Alexandra | Brassinga | F | Connecticut Dermatology Group | 29:17 | 29:29 | 9:30 |
| 372 | 264 | Anne | Mezzapelle | F | GigMasters/The Bash | 28:41 | 29:29 | 9:30 |
| 392 | 265 | Stephanie | Greenman | F | Gilbane Building Company | 29:16 | 29:31 | 9:30 |
| 579 | 266 | Greg | Tweedie | M | Reed Exhibitions | 28:54 | 29:31 | 9:30 |
| 24 | 267 | Josephine | Simko | F | Berkshire Hathaway HomeServices | 29:18 | 29:32 | 9:31 |
| 719 | 268 | Lauren | Deluca | F | Child Guidance Center | 29:19 | 29:33 | 9:31 |
| 561 | 269 | Cybil | Robinson | F | Public Power | 28:59 | 29:38 | 9:33 |
| 137 | 270 | Howard | Kelly | M | Brooks & Falotico | 29:20 | 29:38 | 9:33 |
| 245 | 271 | David | Seah | M | FactSet | 28:57 | 29:39 | 9:33 |
| 85 | 272 | Fred | Post | M | Bridgewater Associates | 29:46 | 29:46 | 9:35 |
| 599 | 273 | Jordan | Olivera | M | Robert Half | 29:40 | 29:49 | 9:36 |
| 354 | 274 | Abbigail | Colucci | F | Gault Family Companies | 29:48 | 29:53 | 9:37 |
| 393 | 275 | Stephen | Verdura | M | Gilbane Building Company | 29:41 | 29:56 | 9:38 |
| 582 | 276 | Jorge | Carreno | M | Reed Exhibitions | 29:20 | 29:58 | 9:39 |
| 255 | 277 | Frank | Celestino | M | FactSet | 29:01 | 29:59 | 9:39 |
| 290 | 278 | Scott | Zintak | M | FactSet | 29:20 | 30:00 | 9:40 |
| 402 | 279 | Chelsey | Brick | F | Inspira marketing Group | 29:29 | 30:05 | 9:41 |
| 694 | 280 | Freddy | Heredia | M | Inspira marketing Group | 30:05 | 30:05 | 9:41 |
| 429 | 281 | Danielle | Haight | F | Kantar | 29:04 | 30:06 | 9:42 |
| 452 | 282 | Nicholas | Mongiardo | M | King Industries Inc. | 29:47 | 30:07 | 9:42 |
| 314 | 283 | Lisa | Valentini | F | FAF-FASB-GASB | 29:53 | 30:07 | 9:42 |
| 647 | 284 | Kevin | Goyen | M | Team Run 169 | 30:07 | 30:09 | 9:43 |
| 112 | 285 | Morgan | Breitmeyer | F | Bridgewater Associates | 30:12 | 30:12 | 9:43 |
| 525 | 286 | Mary | Awad | F | Merritt 7 Venture | 30:17 | 30:17 | 9:45 |
| 205 | 287 | Kenneth | Litt | M | Criterion | 30:24 | 30:24 | 9:47 |
| 633 | 288 | Danielle | Scolpino | F | Tauck | 30:23 | 30:26 | 9:48 |
| 800 | 289 | Lutao | Xie | F | Bridgewater Associates | 30:29 | 30:29 | 9:49 |
| 10 | 290 | Jp | Fragola | M | Akademos | 30:01 | 30:31 | 9:50 |
| 301 | 291 | Zishan | Huang | F | FactSet | 30:32 | 30:32 | 9:50 |
| 560 | 292 | Chelsie | Perone | F | Public Power | 29:58 | 30:37 | 9:52 |
| 631 | 293 | Brian | Shea | M | Tauck | 30:32 | 30:37 | 9:52 |
| 188 | 294 | Meredith | Messina | F | Commonfund | 30:19 | 30:37 | 9:52 |
| 766 | 295 | Jim | O'Brien | M | Commonfund | 30:17 | 30:37 | 9:52 |
| 510 | 296 | Vienna | Ziatyk | F | Melissa & Doug | 30:33 | 30:38 | 9:52 |
| 273 | 297 | Olivia | Parkin | F | FactSet | 29:58 | 30:39 | 9:52 |
| 507 | 298 | Steve | Bordeaux | M | Melissa & Doug | 30:31 | 30:39 | 9:52 |
| 408 | 299 | Taylor | Wilkes | F | Inspira marketing Group | 30:04 | 30:40 | 9:52 |
| 107 | 300 | Melinda | Shaughnessy | F | Bridgewater Associates | 30:28 | 30:42 | 9:53 |
| 53 | 301 | Michele | Massari | F | Blue Buffalo Co. LTD | 30:31 | 30:42 | 9:53 |
| 326 | 302 | Jagjiwan | Singh | M | First County Bank | 30:44 | 30:44 | 9:54 |
| 138 | 303 | Michael | Kudrzycki | M | Brooks & Falotico | 30:18 | 30:45 | 9:54 |
| 246 | 304 | David | Seah | M | FactSet | 30:48 | 30:48 | 9:55 |
| 217 | 305 | Jenifer | Bastoni | F | Datto | 30:49 | 30:49 | 9:56 |
| 480 | 306 | Brian | Barrett | M | Melissa & Doug | 29:57 | 30:50 | 9:56 |
| 289 | 307 | Sara | Rutkowski | F | FactSet | 30:51 | 30:51 | 9:56 |
| 373 | 308 | Brittany | Anderson | F | GigMasters/The Bash | 30:04 | 30:52 | 9:56 |
| 532 | 309 | Melanie | Schlicher | F | Mets Board Americas Corporation | 30:19 | 30:53 | 9:57 |
| 732 | 310 | Beck | Fineman | M | Ryan Ryan Deluca LLP | 30:56 | 30:56 | 9:58 |
| 146 | 311 | Karen | Strauss | F | Cadent Consulting Group | 30:47 | 30:59 | 9:59 |
| 771 | 312 | Lisa | Maybruch | F | Citrin Cooperman | 30:40 | 30:59 | 9:59 |
| 345 | 313 | James | Maccone | M | Foundation Source | 30:19 | 31:01 | 9:59 |
| 531 | 314 | Mallory | Tartaglione | F | Mets Board Americas Corporation | 30:35 | 31:08 | 10:01 |
| 425 | 315 | Gabriel | Bennett | M | Jaffe Holden | 30:47 | 31:08 | 10:02 |
| 253 | 316 | Flint | Mu | M | FactSet | 30:22 | 31:12 | 10:03 |
| 690 | 317 | Devon | Priola | F | Inspira marketing Group | 30:39 | 31:13 | 10:03 |
| 309 | 318 | Gary | Buesser | M | FAF-FASB-GASB | 31:03 | 31:14 | 10:04 |
| 315 | 319 | Rachel | Cole | F | FAF-FASB-GASB | 30:59 | 31:14 | 10:04 |
| 740 | 320 | Gilynett | Montanez | F | Child Guidance Center | 31:02 | 31:15 | 10:04 |
| 580 | 321 | Herve | Sedky | M | Reed Exhibitions | 31:15 | 31:15 | 10:04 |
| 577 | 322 | Dan | Gacetta | M | Reed Exhibitions | 30:38 | 31:16 | 10:04 |
| 528 | 323 | Ashley | Auddino | F | Mets Board Americas Corporation | 30:45 | 31:17 | 10:04 |
| 209 | 324 | Catherine | Stricklan | F | Darien Library | 31:18 | 31:26 | 10:07 |
| 535 | 325 | Bill | Alexander | M | Moran Towing Corp | 31:20 | 31:26 | 10:07 |
| 713 | 326 | Jan | Cajas | M | Kyo Logic | 31:29 | 31:29 | 10:08 |
| 189 | 327 | Randy | Rodgers | M | Commonfund | 31:11 | 31:33 | 10:10 |
| 782 | 328 | Ashley | Avitabile | F | Signal / Charles Taylor | 31:07 | 31:38 | 10:11 |
| 75 | 329 | Christine | Torres | F | Bridgewater Associates | 31:39 | 31:39 | 10:11 |
| 139 | 330 | Tania | Smith | F | Brooks & Falotico | 31:14 | 31:39 | 10:12 |
| 595 | 331 | Miriam | Tomasova | F | Reynolds + Rowella | 31:00 | 31:39 | 10:12 |
| 600 | 332 | Michelle | Kenney | F | Robert Half | 30:48 | 31:40 | 10:12 |
| 642 | 333 | Mike | McGarry | M | Tauck | 31:12 | 31:41 | 10:12 |
| 135 | 334 | Chris | Oberhammer | M | Brooks & Falotico | 31:13 | 31:41 | 10:12 |
| 296 | 335 | Walker | Seaver | M | FactSet | 30:52 | 31:44 | 10:13 |
| 723 | 336 | Clara | Mesa | F | Child Guidance Center | 31:34 | 31:44 | 10:13 |
| 790 | 337 | Kevin | Kelly | M | Kantar | 30:46 | 31:45 | 10:14 |
| 612 | 338 | Christopher | Cesare | M | Rocaton | 31:14 | 31:51 | 10:15 |
| 669 | 339 | Ali | Hasan | M | Wilton Re | 31:17 | 31:52 | 10:16 |
| 772 | 340 | Tom | Scoville | M | Mercer Health & Benefits LLC | 31:53 | 31:53 | 10:16 |
| 603 | 341 | Sal | Cataldo | M | Robert Half | 31:02 | 31:54 | 10:16 |
| 293 | 342 | Shreyas | Valmiki | M | FactSet | 31:10 | 31:54 | 10:17 |
| 791 | 343 | Roel | Smits | | Kantar | 30:56 | 31:58 | 10:18 |
| 493 | 344 | Jake | Warren | M | Melissa & Doug | 31:52 | 31:58 | 10:18 |
| 430 | 345 | David | Sesay | M | Kantar | 31:59 | 31:59 | 10:18 |
| 611 | 346 | Cecily | Tennyson | F | Rocaton | 31:51 | 31:59 | 10:18 |