Found 274 races near Litchfield County, CT

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19

Middletown, CT
• 36.5 miles
$35 -$45
Lace up your sneakers and join us for a day filled with energy, community spirit, and a shared commitment to a meaningful cause. Whether you’re walking, jogging, or running, every step you take...
5K
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19

Hampden, MA
• 45.1 miles
$30 -$40
Join us for the 8th annual 2026 Live Like Scott event, in memory of Scott Godon-Decoteau.  Date: Saturday September 19th, 2026Location: Hampden Memorial Park 495 Main St, Hampden, MA...
24
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Enfield, CT
• 44.3 miles
$30 -$40
9th Annual Outrun Addiction 5K run/walk in Enfield, CT raising addiction awareness.
2m 5K
42
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Farmington, CT
• 21.5 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
11
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20

Darien, CT
• 50.6 miles
$50 -$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...
22
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Newburgh, NY
• 42.5 miles
$10 -$25
Bishop Dunn Memorial School 8th Annual Cupcake 5k Run/ Walk The Sweetest Race in the Hudson Valley !! Sunday, September 20, 2026   Cupcake 5K Run/ Walk Race starts at 9:30am.  The  race will be...
5K
36
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Westport, CT
• 44.6 miles
$20 -$45
Sign up now to take meaningful steps for kids with cancer. Walk with your crew. Run for the challenge, form a team... however you want to participate. Show up in gold🎗️or purple to stand with...
20
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Chester, CT
• 44.7 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
20
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20

Wilton, CT
• 40.1 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
16
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20

Stratford, CT
• 42.7 miles
$25 -$35
Another interesting themed event hatched just last year! And why the heck not? While St Patrick’s is in March this event is a half year warmup  - so join us.  We have the shirts, the snacks and...
5K
19
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Beacon, NY
• 40.3 miles
$25 -$40
WE ARE BACK!!!   I Am Beacon is committed to our mission of offering college scholarships to Beacon seniors. With that, we are excited to announce...   15th Annual | I Run Beacon 5K Run/Walk 2026...
5K
45
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20

Mount Kisco, NY
• 45.1 miles
$5 -$30
The 13th Annual Kisco 5K and Kids Mad Dash will take place on September 20,2026 One of Mount Kisco's favorite events is back for a 13th year and we are excited for the Mount Kisco Volunteer Fire...
5K
21
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Woodbridge, CT
• 24.6 miles
$30 -$45
Family-friendly fun in Woodbridge welcoming runners and walkers of all ages
2m 5K
307
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Ridgefield, CT
• 109.1 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...
4m 8m
24
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26

Middlebury, CT
• 53.8 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
110
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Rhinebeck, NY
• 110.2 miles
$37 -$95
The Hudson Valley’s favorite autumn tradition returns. Whether you’re using our half marathon as the final "big push" before your fall championship or taking on the 5K for the sheer atmosphere of...
5K Half Marathon
82
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Ramsey, NJ
• 67.3 miles
$25 -$50
Jack McKeown devoted over 40 years to coaching Ramsey Baseball and developing the Ramsey Recreation Department before he passed in 1997. He was named the Ramsey Recreation Director and the Ramsey...
5K 10K
21
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Portland, CT
• 66.7 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
55
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Cromwell, CT
• 33.9 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
12
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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
72