Upcoming Races Near Cheshire, CT in May, 2026

Name: 2025 Weston CT Memorial Day Weekend 5K Road Race
Start: 2026-05-23
End: 2026-05-23
Location: Weston

4th Annual Sail to the Finish 2M Run

Middlebury, CT

Saturday, May 2nd, 2026

Featured

View details for race 4th Annual Sail to the Finish 2M Run

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Roxbury Road Race Series #9

Roxbury, CT

Saturday, May 2nd, 2026

View details for race Roxbury Road Race Series #9

St.Mary-St.Michael School 1 Mile Run

Derby, CT

Saturday, May 2nd, 2026

1 Mile

View details for race St.Mary-St.Michael School 1 Mile Run

Brew Run

New London, CT

Saturday, May 2nd, 2026

1 Mile

View details for race Brew Run

Cinco K Mayo 5k Run/Walk

Enfield, CT

Saturday, May 2nd, 2026

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

Rising Stars Training Program Session One Prese...

Glastonbury, CT

Saturday, May 2nd, 2026

View details for race Rising Stars Training Program Session One Presented by SmartStart Pediatrics

2026 Granby Road Race

Granby, CT

Saturday, May 2nd, 2026

10K

1 Mile

View details for race 2026 Granby Road Race

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

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

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

Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

View details for race Miles For Margaritas

Breast Cancer Alliance 5K for Hope

Greenwich, CT

Sunday, May 3rd, 2026

View details for race Breast Cancer Alliance 5K for Hope

Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

View details for race Glenholme 5K Run For Autism

Healthy Kids Running Series Spring 2026 - South...

Southwick, MA

Sunday, May 3rd, 2026

View details for race Healthy Kids Running Series Spring 2026 - Southwick, MA

Glenbrook Middle School Bulldog Dash

Longmeadow, MA

Sunday, May 3rd, 2026

View details for race Glenbrook Middle School Bulldog Dash

Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

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CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

View details for race CTA Scholarship 5k Run/Walk

Virtual Run Like A Mother 5k & Kids 1 Mile

Ridgefield, CT

Thursday, May 7th, 2026

1 Mile

View details for race Virtual Run Like A Mother 5k & Kids 1 Mile

Roxbury Road Race Series #10

Roxbury, CT

Saturday, May 9th, 2026

View details for race Roxbury Road Race Series #10

2nd Annual Camp Mountain Laurel - Color Run & T...

Hamden, CT

Saturday, May 9th, 2026

View details for race 2nd Annual Camp Mountain Laurel - Color Run & Trail Run

Sacandaga Sprint 5k

Northville, NY

Saturday, May 9th, 2026

View details for race Sacandaga Sprint 5k

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

Saint James, NY

Saturday, May 9th, 2026

Fast

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MY MOTHER MADE ME DO IT 1 Mile Mother'...

Prospect, CT

Saturday, May 9th, 2026

1 Mile

View details for race MY MOTHER MADE ME DO IT 1 Mile Mother's Day Race

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

Mother's Day 5K

Yorktown Heights, NY

Sunday, May 10th, 2026

View details for race Mother's Day 5K

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

Vernon Mothers Day Dash 5K

Vernon, CT

Sunday, May 10th, 2026

View details for race Vernon Mothers Day Dash 5K

WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

View details for race WeCare-Mother's Day 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

Roxbury Road Race Series #11

Roxbury, CT

Saturday, May 16th, 2026

View details for race Roxbury Road Race Series #11

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

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

Bailey's Garden 5K

Lebanon, CT

Saturday, May 16th, 2026

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Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

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Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

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2026 CACNA1A 5K

Norwalk, CT

Saturday, May 16th, 2026

View details for race 2026 CACNA1A 5K

RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

View details for race RESERVOIR RUSH

Newington Library 5K Challenge

Newington, CT

Sunday, May 17th, 2026

View details for race Newington Library 5K Challenge

Strong Family Farm Chicken Run

Vernon, CT

Sunday, May 17th, 2026

View details for race Strong Family Farm Chicken Run

Rossiter Run 2026

Washington Depot, CT

Sunday, May 17th, 2026

View details for race Rossiter Run 2026

Running Battles- A Race To The Finish

Wolcott, CT

Sunday, May 17th, 2026

View details for race Running Battles- A Race To The Finish

Blueberry Hill 2026 Spring Shuffle - Run, Walk,...

Longmeadow, MA

Sunday, May 17th, 2026

View details for race Blueberry Hill 2026 Spring Shuffle - Run, Walk, Roll!

Celebrate Kate 5k

Springfield, MA

Sunday, May 17th, 2026

View details for race Celebrate Kate 5k

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

Miles for Mary Run/Walk

Westfield, MA

Sunday, May 17th, 2026

1 Mile

View details for race Miles for Mary Run/Walk

Guardian Revival 5k

Carmel, NY

Sunday, May 17th, 2026

View details for race Guardian Revival 5k

Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

View details for race Spring Run The Farm

"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

Cpl Christopher G. Scherer "I Did The Grid"

East Northport, NY

Saturday, May 23rd, 2026

1 Mile

View details for race Cpl Christopher G. Scherer "I Did The Grid"

2025 Weston CT Memorial Day Weekend 5K Road Race

Weston, CT

Saturday, May 23rd, 2026

1 Mile

View details for race 2025 Weston CT Memorial Day Weekend 5K Road Race

Explore more in Cheshire, CT

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

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