Upcoming 5K Races Near Cheshire, CT

Name: Run the Vineyards - Memorial Day at Pindar 5K
Start: 2026-05-24
End: 2026-05-24
Location: Peconic

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

Featured

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2026 Granby Road Race

Granby, CT

Saturday, May 2nd, 2026

10K

1 Mile

View details for race 2026 Granby Road Race

Brew Run

New London, CT

Saturday, May 2nd, 2026

1 Mile

View details for race Brew Run

FES PTO Chocolate Truffle Shuffle 5K Trail Run

North Franklin, CT

Saturday, May 2nd, 2026

View details for race FES PTO Chocolate Truffle Shuffle 5K Trail Run

The Iger Fund 5K: Hosted by The Be Kind Project

Hartford, CT

Saturday, May 2nd, 2026

View details for race The Iger Fund 5K: Hosted by The Be Kind Project

Cinco K Mayo 5k Run/Walk

Enfield, CT

Saturday, May 2nd, 2026

View details for race Cinco K Mayo 5k Run/Walk

AEF May the Course Be With You 5K

Lagrangeville, NY

Saturday, May 2nd, 2026

1 Mile

View details for race AEF May the Course Be With You 5K

Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

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Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

View details for race Miles For Margaritas

CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

View details for race CTA Scholarship 5k Run/Walk

Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

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Glenbrook Middle School Bulldog Dash

Longmeadow, MA

Sunday, May 3rd, 2026

View details for race Glenbrook Middle School Bulldog Dash

Breast Cancer Alliance 5K for Hope

Greenwich, CT

Sunday, May 3rd, 2026

View details for race Breast Cancer Alliance 5K for Hope

St. James 5 Mile Challenge and 5K Fun Run/Walk

Saint James, NY

Saturday, May 9th, 2026

Fast

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Sacandaga Sprint 5k

Northville, NY

Saturday, May 9th, 2026

View details for race Sacandaga Sprint 5k

Run Like a Mother 5K and Kid's 1-Mile 2026

Ridgefield, CT

Sunday, May 10th, 2026

1 Mile

View details for race Run Like a Mother 5K and Kid's 1-Mile 2026

Milford Campus Bridgeport Hospital Mother's Day...

Milford, CT

Sunday, May 10th, 2026

View details for race Milford Campus Bridgeport Hospital Mother's Day 5K Run/Walk, 3K - Walkers only and Kids Fun Run

Mother's Day 5K

Yorktown Heights, NY

Sunday, May 10th, 2026

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WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

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Vernon Mothers Day Dash 5K

Vernon, CT

Sunday, May 10th, 2026

View details for race Vernon Mothers Day Dash 5K

Stamford Boys & Girls Club Corporate 5K at Mill...

Stamford, CT

Thursday, May 14th, 2026

View details for race Stamford Boys & Girls Club Corporate 5K at Mill River Park

Dan the Man 5K Run/Walk for ALS

Berlin, CT

Saturday, May 16th, 2026

View details for race Dan the Man 5K Run/Walk for ALS

Quiet Corner Winery First Annual Alzheimer’s Fu...

Hampton, CT

Saturday, May 16th, 2026

View details for race Quiet Corner Winery First Annual Alzheimer’s Fundraiser 5K

Lauren's Haven 5K Run/ Walk

Springfield, MA

Saturday, May 16th, 2026

View details for race Lauren's Haven 5K Run/ Walk

Teacher vs Students 5K

Cromwell, CT

Saturday, May 16th, 2026

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Bailey's Garden 5K

Lebanon, CT

Saturday, May 16th, 2026

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RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

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2026 CACNA1A 5K

Norwalk, CT

Saturday, May 16th, 2026

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Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

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End the Stigma: Mental Health Awareness 5K

New London, CT

Saturday, May 16th, 2026

View details for race End the Stigma: Mental Health Awareness 5K

Somers Summer Series

Somers, CT

Sunday, May 17th, 2026

Trail

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The Follow Natural Fitness Women's Health 5K

Bridgeport, CT

Sunday, May 17th, 2026

1 Mile

View details for race The Follow Natural Fitness Women's Health 5K

Spring Shuffle - Run, Walk, Roll!

Longmeadow, MA

Sunday, May 17th, 2026

View details for race Spring Shuffle - Run, Walk, Roll!

Miles for Mary Run/Walk

Westfield, MA

Sunday, May 17th, 2026

1 Mile

View details for race Miles for Mary Run/Walk

FreeFromEvil 5k Race/Walk

Waterbury, CT

Sunday, May 17th, 2026

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Celebrate Kate 5k

Springfield, MA

Sunday, May 17th, 2026

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"Using our Voices" Mental Health Run- Patchogue...

Medford, NY

Sunday, May 17th, 2026

1 Mile

View details for race "Using our Voices" Mental Health Run- Patchogue-Medford

2026 Rossiter Run 5K Race and Fun Run/Walk

Washington Depot, CT

Sunday, May 17th, 2026

View details for race 2026 Rossiter Run 5K Race and Fun Run/Walk

Outrun Hunger 5K race - and 1-mile fun walk

Springfield, MA

Sunday, May 17th, 2026

1 Mile

View details for race Outrun Hunger 5K race - and 1-mile fun walk

Guardian Revival 5K

Carmel, NY

Sunday, May 17th, 2026

View details for race Guardian Revival 5K

Strong Family Farm Chicken Run

Vernon, CT

Sunday, May 17th, 2026

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Newington Library 5K Challenge

Newington, CT

Sunday, May 17th, 2026

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Spring Into Spring Glen 5K

Hamden, CT

Sunday, May 17th, 2026

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Get Smart for Wilton 5K

Wilton, CT

Friday, May 22nd, 2026

Fast

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5K Walk/Jog/Run for Jon

Woodbury, CT

Saturday, May 23rd, 2026

View details for race 5K Walk/Jog/Run for Jon

32nd Annual | Weston Memorial Day Weekend 5K & ...

Weston, CT

Saturday, May 23rd, 2026

1 Mile

View details for race 32nd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run

Dustin L. Doyon Memorial Road Race

Suffield, CT

Saturday, May 23rd, 2026

10K

View details for race Dustin L. Doyon Memorial Road Race

Cpl. Christopher G. Scherer Memorial "I Did the...

East Northport, NY

Saturday, May 23rd, 2026

1 Mile

View details for race Cpl. Christopher G. Scherer Memorial "I Did the Grid" 5K Run/Walk

Savin Rock Waves of Hope

West Haven, CT

Saturday, May 23rd, 2026

View details for race Savin Rock Waves of Hope

America's 250 Celebration Color Run 5K

Ledyard, CT

Sunday, May 24th, 2026

View details for race America's 250 Celebration Color Run 5K

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

1 Mile

Trail

View details for race Run the Vineyards - Memorial Day at Pindar 5K

Explore more in Cheshire, CT

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

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