Found 288 races

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SEP
19

Enfield, CT
• 17.8 miles
$30 -$40
The 9th Annual Outrun Addiction 5K will take place on Saturday, September 19th, 2026 Please join us for this 5K Run/Walk and 2 Mile Walk. Unable to join us on that day? Choose the option of...
2m 5K
17
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20

Dayville, CT
• 41.0 miles
$5 -$30
We are thrilled to share that our 14th annual ~Lap the Lake~ Road Race & Walk has been scheduled for Sunday, September 20, 2026! ~Lap the Lake~ is a major fundraising event which helps fund all...
2m 5K
1
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20

Farmington, CT
• 8.5 miles
$35
Race Location: 50 Winding Trails Drive, Farmington, CTRace Time: 9am Registration and 10am Race Start Farmington River 5K Trail Race will be held on Sunday, 9/20/2025. The race will be held on...
5K
3
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20

Darien, CT
• 64.9 miles
$45 -$55
For 46 years, The Community Fund of Darien has brought the community together for the annual Darien Road Race & Family Fun Day. This beloved fall event features two races—a 1.5-mile Timed...
7
SEP
20

Westport, CT
• 56.1 miles
$20 -$35
Join us for our 12th Annual Walk/Run supporting kids with cancer right here in Connecticut.  
5K
1
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20

Chester, CT
• 25.6 miles
$20 -$40
Choose between a 4 or 9 mile trail race in the Cockaponsett State Forest in Chester, CT.  The 4 miler is the first part of the 9 mile course. The course consists of roots, rocks, muddy sections...
4m 9m
7
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20

Wilton, CT
• 55.5 miles
$25 -$30
A community event presented by Wilton Pride & Wilton Library Join Wilton Pride and Wilton Library for the Third  Annual Come Out & Run 5K celebrating PRIDE, diversity, inclusivity, and the spirit...
5K
1
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20

Woodbridge, CT
• 32.8 miles
$25 -$45
Family-friendly fun in Woodbridge welcoming runners and walkers of all ages
2m 5K
284
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20

Ridgefield, CT
• 52.0 miles
$50 -$65
                          Where the Pavement Ends Trail Races are set for Sunday, September 20, 2026                             You can do one loop of the course or do two loops for a “Pavement...
12
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26

Middlebury, CT
• 28.3 miles
$35 -$50
Race Date: Saturday, September 26, 2026 Start Time: 9:00 AM Location: Pies & Pub · 1 Store Road, Middlebury, CT Benefiting: American Cancer Society's Making Strides Against Breast Cancer...
5K
83
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26

Meriden, CT
• 17.0 miles
$30 -$40
Get ready to lace up your running shoes and make a difference at the Chamber Challenge 5K. Presented by the Midstate Chamber of Commerce Health & Wellness Council and the Young Business Leaders...
5K
3
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26

Portland, CT
• 13.2 miles
$20 -$30
Portland Come on Over 5K Race Information - Online Registration only Date: Saturday, September 27, 2025, Rain or Shine Start Time: 10:00 AM Location: Portland Riverfront Park, 284 Brownstone...
2m 5K
36
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26

Cromwell, CT
• 12.7 miles
$25 -$30
This race will kick off day three of the Cromwell Riverport Festival!  Over half the course is run parallel to the CT river, starting at River Front Park with a turnaround at the beautiful...
5K
3
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26

Redding, CT
• 49.7 miles
$15 -$45
Ready, Set, RACE!Join us for the first annual New Pond Farm Hayfield Hustle! Choose from a scenic 5 mile, 5k, or Children's Sap fun run through the hayfields and byways of New Pond Farm, all...
5K 5m
16
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26

Colebrook, CT
• 26.4 miles
$60
2026 Hogsback Half Marathon Information: Start Time: 8:30 a.m. on September 26, 2026.   Amenities: Rural course on lightly travelled country roads along the Farmington River;Amazing race shirts;6...
Half Marathon
32
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26

New Haven, CT
• 34.0 miles
$25
Participants may walk, run or bike on Saturday September 20th, 2025 at East Rock Park!  The event takes place at College Woods in East Rock Park. 5K participants will run along the Mill River and...
5K
27
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26

Simsbury, CT
• 9.8 miles
$30 -$45
The River Run will take place Saturday September 9/26/2026 10:00 am in picturesque Simsbury, Connecticut.  Featuring USATF certified 5k and 10k road races as well as 1 mile & 1/2 mile kid's...
5K 10K
40
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27

Morris, CT
• 27.4 miles
$30
Connecticut's Newest Lake Road Race!  The Beach to Beach 5K offers scenic views of Bantam Lake with rolling hills and a fast finish at Morris Town Beach. All proceeds of the race go to the Bantam...
5K
3
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27

Stafford Springs, CT
• 23.9 miles
$20 -$40
SAVE THE DATE!! Bosco Fowler Memorial 5K Run/Walk  |  Sunday, September 27, 2026 The Rotary Club of Stafford CT is proud to sponsor the 4th Annual Bosco Fowler Memorial 5K Road Race. Join us at...
5K
3
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27

Lisbon, CT
• 36.0 miles
$25 -$30
Join us for the 44th Lisbon Fall Festival Road Race on Sunday, September 27, 2026. 10:00 am race start. The 5k course is over gentle rolling hills through the rural town of Lisbon, CT.  RACE...
5K
4