Best Races in Connecticut

Best 5Ks in Connecticut

1. 1 2026 Colony Grill 'Hot Oil' 5K Fairfield, CT Nov 2026 51.7/100 FLDHSTCRDCHR
2. 2 18th Annual Saybrook Point 5k Road Race Old Saybrook, CT Aug 2027 47.1/100 FLDHSTCRDCHR
3. 3 14th Annual Miles for a Mission 5K Run/Walk – In Person AND Virtual – benefiting INTEMPO Stamford, CT Sep 2026 41.2/100 FLDHSTCRDCHR
4. 4 4th Annual Beach to Beach 5k Morris, CT Sep 2026 38.9/100 FLDHSTCRDCHR
5. 5 4th Annual Pumpkin Run Harwinton 5K & Kids Dash Harwinton, CT Oct 2026 37.8/100 FLDHSTCRDCHR
6. 6 5th Annual Purple Light Project 5K Hartford, CT Oct 2026 37.7/100 FLDHSTCRDCHR

Every ranked race in Connecticut

Composite /100 · FLD field · HST history · CRD credentials · CHR character

1. 1 42nd Annual Lake Waramaug Polar Bear Run Warren, CT Feb 2027 58.2/100 FLDHSTCRDCHR
2. 2 2026 Colony Grill 'Hot Oil' 5K Fairfield, CT Nov 2026 51.7/100 FLDHSTCRDCHR
3. 3 18th Annual Saybrook Point 5k Road Race Old Saybrook, CT Aug 2027 47.1/100 FLDHSTCRDCHR
4. 4 14th Annual Miles for a Mission 5K Run/Walk – In Person AND Virtual – benefiting INTEMPO Stamford, CT Sep 2026 41.2/100 FLDHSTCRDCHR
5. 5 4th Annual Beach to Beach 5k Morris, CT Sep 2026 38.9/100 FLDHSTCRDCHR
6. 6 4th Annual Pumpkin Run Harwinton 5K & Kids Dash Harwinton, CT Oct 2026 37.8/100 FLDHSTCRDCHR
7. 7 5th Annual Purple Light Project 5K Hartford, CT Oct 2026 37.7/100 FLDHSTCRDCHR

Longest-running in Connecticut

10 races we can date but haven't measured enough of to score. Oldest first. What we measure →

1. 1 34th Annual Halloween 5K and Kids Fun Run Brookfield, CT Oct 2026 1993 33 years running
2. 2 17th Annual Farmington River Run 5K Trail Race Farmington, CT Sep 2026 2010 16 years running
3. 3 15th Annual Milford 5K Trick or Trot Run/Walk Milford, CT Oct 2026 2012 14 years running
4. 4 14th Annual NOW ~Lap The Lake~ 5k Walk & Run Dayville, CT Sep 2026 2013 13 years running
5. 5 13th Annual Run Back to School 5K, 1 Mile Race & Fun Run Weatogue, CT Oct 2026 2014 12 years running
6. 6 EDRRC - 8th Annual Schaghticoke 8.5 Miler Kent, CT Nov 2026 2019 7 years running
7. 7 6th Annual Roseland Park Christmas Run 5K & Kids Fun Run Woodstock, CT Dec 2026 2021 5 years running
8. 8 4th Annual OAH STRIDES Race and Family Fun Day Simsbury, CT Oct 2026 2023 3 years running
9. 9 2nd Annual PCS Harvest Hustle 5K & Kids Run Pomfret Center, CT Sep 2026 2025 1 year running
10. 10 3rd Annual Camp Mountain Laurel - Color Run & Trail Run Hamden, CT May 2027 2025 1 year running

Also listed, not yet ranked

75 races we list but haven't measured enough of to score. By date. What we measure →

1. – 2026 Dave Parcells Madison Triathlon Madison, CT Sep 2026 Not yet rankedno verified data
2. – 2026 Farmington Memorial Walk & Kids' Fun Run Farmington, CT Sep 2026 Not yet rankedno verified data
3. – 2026 Lyme Hunter Pace Lyme, CT Sep 2026 Not yet rankedno verified data
4. – EDRRC - High Watch Recovery Center's Sprint for Sobriety 5K Run/Walk Kent, CT Sep 2026 Not yet rankedno verified data
5. – Avon XC Home Meet Avon, CT Sep 2026 Not yet rankedno verified data
6. – Cheshire Community YMCA Harvest Trail Race and Y Cup Relay Cheshire, CT Sep 2026 Not yet rankedno verified data
7. – 2026 Run To The River 5K Deep River, CT Sep 2026 Not yet rankedno verified data
8. – 4 Town 5k Somers, CT Sep 2026 Not yet rankedno verified data
9. – ABC Laps For Life 5k Middletown, CT Sep 2026 Not yet rankedno verified data
10. – Arc Run Meriden, CT Sep 2026 Not yet rankedno verified data
11. – Bound for the Sound Old Lyme, CT Sep 2026 Not yet rankedno verified data
12. – Bozrah Fire Department 5k Road Race and Kids' fun run Bozrah, CT Sep 2026 Not yet rankedno verified data
13. – Connecticut River Valley Invitational Cromwell, CT Sep 2026 Not yet rankedno verified data
14. – 2026 Darien Road Race & Family Fun Day Charity Fundraiser Darien, CT Sep 2026 Not yet rankedno verified data
15. – Circle of Care's Annual Walk/Run for Kids With Cancer Westport, CT Sep 2026 Not yet rankedno verified data
16. – Cockaponsett Trails to a Cure Chester, CT Sep 2026 Not yet rankedno verified data
17. – Come Out & Run 5k Wilton, CT Sep 2026 Not yet rankedno verified data
18. – 2026 Pies & Pub TaTa Trot 5k Middlebury, CT Sep 2026 Not yet rankedno verified data
19. – Chamber Challenge 5K Meriden, CT Sep 2026 Not yet rankedno verified data
20. – Come on Over 5K and 2.1 Mile Fitness Walk Portland, CT Sep 2026 Not yet rankedno verified data
21. – Cromwell Riverport 5k Cromwell, CT Sep 2026 Not yet rankedno verified data
22. – Bosco Fowler Memorial 5K Road Race Stafford Springs, CT Sep 2026 Not yet rankedno verified data
23. – Central CT Open Water Swim Marlborough, CT Sep 2026 Not yet rankedno verified data
24. – Answer the Bell Full - 100 Mile + (100 Miler) - Complete a 1.2 mile, 600 foot loop every hour, on the hour, for up to 84 hours, until you can no longer answer the bell. - Elevation Endurance Ultra Backyard Trail Marathon - 100 + Miles | 84 Hour - IronHike (Iron Hike) Fall (October / Oct) - Solo - Mohawk Mountain, Connecticut (CT) - Run, hike, or walk with us as we redefine race day. Cornwall, CT Oct 2026 Not yet rankedno verified data
25. – Denali - 40 Mile + (40 Miler) - if you can only spare your whole weekend - Elevation Endurance Ultra Trail Marathon - 43 + Miles | 48 Hour - IronHike (Iron Hike) Fall (October / Oct) - Relay - Mohawk Mountain, Connecticut (CT) - Run, Hike or Walk with us as we redefine race day. Cornwall, CT Oct 2026 Not yet rankedno verified data
26. – Denali - 40 Mile + (40 Miler) - if you can only spare your whole weekend - Elevation Endurance Ultra Trail Marathon - 43 + Miles | 48 Hour - IronHike (Iron Hike) Fall (October / Oct) - Solo - Mohawk Mountain, Connecticut (CT) - Run, Hike or Walk with us as we redefine race day. Cornwall, CT Oct 2026 Not yet rankedno verified data
27. – Cider Mill Road Race Tolland, CT Oct 2026 Not yet rankedno verified data
28. – Dana's Angels Research Trust's 2026 "DART To The Finish" 2 Mile Walk to Cure Niemann-Pick type C Disease Old Greenwich, CT Oct 2026 Not yet rankedno verified data
29. – 2026 Groton Memorial Walk & Kids' Fun Run Groton, CT Oct 2026 Not yet rankedno verified data
30. – Anda! 5k New Haven, CT Oct 2026 Not yet rankedno verified data
31. – Apple Harvest Road Races Southington, CT Oct 2026 Not yet rankedno verified data
32. – Big Sky 5K and Kids 1 mile Dash Farmington, CT Oct 2026 Not yet rankedno verified data
33. – Capalbo Strong Walk Fairfield, CT Oct 2026 Not yet rankedno verified data
34. – 2026 Footprints on our Hearts Walk & 5K Meriden, CT Oct 2026 Not yet rankedno verified data
35. – Benhaven Walk for Autism New Haven, CT Oct 2026 Not yet rankedno verified data
36. – Country School XC Invitational Madison, CT Oct 2026 Not yet rankedno verified data
37. – All Hallows Eve 5K Hampton, CT Oct 2026 Not yet rankedno verified data
38. – Cider Run/Walk 5k Warren, CT Oct 2026 Not yet rankedno verified data
39. – Coast Guard Foundation - Run to Remember 5k Road Race & Walk New London, CT Oct 2026 Not yet rankedno verified data
40. – Consumer Reports 5K Colchester, CT Oct 2026 Not yet rankedno verified data
41. – 2026 Run for The Cove 5K & Memorial Walk Madison, CT Oct 2026 Not yet rankedno verified data
42. – Addy’s Run 5K Waterford, CT Oct 2026 Not yet rankedno verified data
43. – Bristol Mum-A-Thon Road Race 2026 Bristol, CT Oct 2026 Not yet rankedno verified data
44. – Berkshire League Cross Country Championships Watertown, CT Oct 2026 Not yet rankedno verified data
45. – Andover Norton Commission Trick or Trot 5K Run/Walk and Kids 1 K Fun Run Andover, CT Oct 2026 Not yet rankedno verified data
46. – Chasing the Legend; Easton's Lady in White 5K Run/Walk Easton, CT Oct 2026 Not yet rankedno verified data
47. – Easterseals Freedom Stride Hartford, CT Oct 2026 Not yet rankedno verified data
48. – 5K for Ballet! East Hampton, CT Oct 2026 Not yet rankedno verified data
49. – Abner Oakes III Veterans Run 5K & 10K Hamden, CT Oct 2026 Not yet rankedno verified data
50. – Connecticut Law Enforcement Officers Memorial Run Middletown, CT Oct 2026 Not yet rankedno verified data
51. – Crosby Sports Hall of Fame Fall into Fall 4k Waterbury, CT Oct 2026 Not yet rankedno verified data
52. – Donny's Dash Simsbury, CT Oct 2026 Not yet rankedno verified data
53. – CFA 5K Run & Walk for Mental Health Groton, CT Oct 2026 Not yet rankedno verified data
54. – Collinsville Trick or Trot Collinsville, CT Oct 2026 Not yet rankedno verified data
55. – Air Line Trail Ghost Run Hebron, CT Nov 2026 Not yet rankedno verified data
56. – CT Veterans Day Race Coventry, CT Nov 2026 Not yet rankedno verified data
57. – East Windsor Veterans Day 5K Road Race Broad Brook, CT Nov 2026 Not yet rankedno verified data
58. – Centerville Bank Thompson Turkey Trot Thompson, CT Nov 2026 Not yet rankedno verified data
59. – A Good Run 5K New Haven, CT Nov 2026 Not yet rankedno verified data
60. – Electric Boat Athletic Club (EBAC) Fall Challenge New London, CT Nov 2026 Not yet rankedno verified data
61. – Annual Kiwanis Turkey Trot Road Race Wallingford, CT Nov 2026 Not yet rankedno verified data
62. – 2026 Southbury Turkey Trot 5K & Kids Fun Run Southbury, CT Nov 2026 Not yet rankedno verified data
63. – Bethel Turkey Trot Bethel, CT Nov 2026 Not yet rankedno verified data
64. – Branford Thanksgiving 5K Branford, CT Nov 2026 Not yet rankedno verified data
65. – Commodore Hull Thanksgiving Day 5k Road Race Shelton, CT Nov 2026 Not yet rankedno verified data
66. – 2026 Jingle Bell Run - Connecticut North Haven, CT Dec 2026 Not yet rankedno verified data
67. – Christopher Martin's Christmas Run for Children New Haven, CT Dec 2026 Not yet rankedno verified data
68. – CLA Blue Back Mitten Run West Hartford, CT Dec 2026 Not yet rankedno verified data
69. – 2025 Norwalk Jingle Bell 5K Norwalk, CT Dec 2026 Not yet rankedno verified data
70. – Brookfield Lions Run for Sight 4-Miler Brookfield, CT Jan 2027 Not yet rankedno verified data
71. – 99.1 PLR *Shamrock and Roll 5K* New Haven, CT Mar 2027 Not yet rankedno verified data
72. – Catch A Leprechaun 5K Essex, CT Mar 2027 Not yet rankedno verified data
73. – 2027 Granby Road Race Granby, CT May 2027 Not yet rankedno verified data
74. – Brew Run New London, CT May 2027 Not yet rankedno verified data
75. – 2026 Rossiter Run 5K Race and Fun Run/Walk Washington Depot, CT May 2027 Not yet rankedno verified data