Upcoming 5K Races Near Middlebury, CT

Name: Pleasantville 5K Run/Walk for Education
Start: 2026-05-16
End: 2026-05-16
Location: Pleasantville

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

Featured

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KIM’S KINDNESS 5K

Mattituck, NY

Saturday, April 18th, 2026

View details for race KIM’S KINDNESS 5K

Naugatuck YMCA & Rotary 5K

Naugatuck, CT

Saturday, April 18th, 2026

View details for race Naugatuck YMCA & Rotary 5K

Race for YOUR Mental Health

Meriden, CT

Saturday, April 18th, 2026

View details for race Race for YOUR Mental Health

SRC 5k, 10k, Half Marathon

Stamford, CT

Sunday, April 19th, 2026

10K

Half

View details for race SRC 5k, 10k, Half Marathon

TOMMY SULLIVAN 5K RUN/WALK

BRANFORD Connecticut 06405, CT

Sunday, April 19th, 2026

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Crusaders Crush Cancer

White Plains, NY

Sunday, April 19th, 2026

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Tommy Sullivan's 5K

Branford, CT

Sunday, April 19th, 2026

Trail

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Gilbert Joseph & Brian Annual 5K (Gilbert JBA5K)

Winsted, CT

Saturday, April 25th, 2026

View details for race Gilbert Joseph & Brian Annual 5K (Gilbert JBA5K)

Puzzles 5k

Danbury, CT

Saturday, April 25th, 2026

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Run PB's Spring into Running

Peekskill, NY

Saturday, April 25th, 2026

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Shane Kinsella Memorial 5K Run or 2M Walk

Goshen, CT

Saturday, April 25th, 2026

View details for race Shane Kinsella Memorial 5K Run or 2M Walk

The Sachem SEPTA Any Pace Race!

Ronkonkoma, NY

Saturday, April 25th, 2026

Fast

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Deacon Chuck Dietsch Memorial 5K Run & Walk for...

Southbury, CT

Saturday, April 25th, 2026

View details for race Deacon Chuck Dietsch Memorial 5K Run & Walk for Haiti

The Jeet Patel Memorial 5k

New Haven, CT

Saturday, April 25th, 2026

View details for race The Jeet Patel Memorial 5k

PK5K Wellness Run/Walk

Poughkeepsie, NY

Saturday, April 25th, 2026

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Holy Rosary Sole to Soul 5k

Hawthorne, NY

Saturday, April 25th, 2026

1 Mile

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The Mommy Dash 5K To Benefit the Terry D'Amato ...

Wappingers Falls, NY

Sunday, April 26th, 2026

View details for race The Mommy Dash 5K To Benefit the Terry D'Amato Scholarship Fund

Superhero Sunday 5K, Kids Mile, Community Bash

Wethersfield, CT

Sunday, April 26th, 2026

1 Mile

View details for race Superhero Sunday 5K, Kids Mile, Community Bash

Run For Veterans

Guilford, CT

Sunday, April 26th, 2026

10K

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Julia's Run for Children

New Haven, CT

Sunday, April 26th, 2026

1 Mile

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2026 Minute Man Race

Westport, CT

Sunday, April 26th, 2026

10K

View details for race 2026 Minute Man Race

East Farms Spring Ahead 5k & 1M Fun Run

Farmington, CT

Sunday, April 26th, 2026

1 Mile

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NORTH FORK ENVIRONMENTAL COUNCIL EARTH DAY 5K

Riverhead, NY

Sunday, April 26th, 2026

View details for race NORTH FORK ENVIRONMENTAL COUNCIL EARTH DAY 5K

Daffodil Dash 5K

Meriden, CT

Sunday, April 26th, 2026

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12th Annual Chocolate 5K Road Race

New Windsor, NY

Sunday, April 26th, 2026

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Cinco K Mayo 5k Run/Walk

Enfield, CT

Saturday, May 2nd, 2026

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FES PTO Chocolate Truffle Shuffle 5K Trail Run

North Franklin, CT

Saturday, May 2nd, 2026

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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

FISHKILL FREEDOM 5K FESTIVAL & 1 MI FUN RUN

Fishkill, NY

Saturday, May 2nd, 2026

View details for race FISHKILL FREEDOM 5K FESTIVAL & 1 MI FUN RUN

AEF May the Course Be With You 5K

Lagrangeville, NY

Saturday, May 2nd, 2026

1 Mile

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2026 Granby Road Race

Granby, CT

Saturday, May 2nd, 2026

10K

1 Mile

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Bretton Woods 5k Run/Walk for ALS Ride for Life

Hauppauge, NY

Saturday, May 2nd, 2026

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Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

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CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

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Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

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Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

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Glenbrook Middle School Bulldog Dash

Longmeadow, MA

Sunday, May 3rd, 2026

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Breast Cancer Alliance 2025 5K for Hope Run/Walk

Greenwich, CT

Sunday, May 3rd, 2026

View details for race Breast Cancer Alliance 2025 5K for Hope 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

The Charlie Goldberger Loucks 5K Presented by T...

White Plains, NY

Saturday, May 9th, 2026

View details for race The Charlie Goldberger Loucks 5K Presented by The Loucks Games and The White Plains Rotary

Sacandaga Sprint 5K/10K/ and Kids Fun Run

Northville, NY

Saturday, May 9th, 2026

10K

View details for race Sacandaga Sprint 5K/10K/ and Kids Fun Run

Safe Harbors of the Hudson Run/Walk 5K

Newburgh, NY

Saturday, May 9th, 2026

View details for race Safe Harbors of the Hudson Run/Walk 5K

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

Saint James, NY

Saturday, May 9th, 2026

Fast

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Mother's Day 5K

Yorktown Heights, NY

Sunday, May 10th, 2026

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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

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

Ridgefield, CT

Sunday, May 10th, 2026

1 Mile

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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

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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

Pleasantville 5K Run/Walk for Education

Pleasantville, NY

Saturday, May 16th, 2026

1 Mile

View details for race Pleasantville 5K Run/Walk for Education

Explore more in Middlebury, CT

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

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