Upcoming Races Near Middlebury, CT in May, 2026

Name: The Follow Natural Fitness Women's Health 5K
Start: 2026-05-17
End: 2026-05-17
Location: Bridgeport

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

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View details for race Hat City Dash

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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

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

Hauppauge, NY

Saturday, May 2nd, 2026

View details for race Bretton Woods 5k Run/Walk for ALS Ride for Life

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

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

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

Roxbury Road Race Series #9

Roxbury, CT

Saturday, May 2nd, 2026

View details for race Roxbury Road Race Series #9

Cinco K Mayo 5k Run/Walk

Enfield, CT

Saturday, May 2nd, 2026

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

4th Annual Sail to the Finish 2M Run

Middlebury, CT

Saturday, May 2nd, 2026

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

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

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

Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

View details for race Glenholme 5K Run For Autism

Track & Suffield 2 Miler

Suffield, CT

Sunday, May 3rd, 2026

View details for race Track & Suffield 2 Miler

Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

View details for race Miles For Margaritas

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

Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

View details for race Mount Archer Trail Race

CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

View details for race CTA Scholarship 5k Run/Walk

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

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

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

Roxbury Road Race Series #10

Roxbury, CT

Saturday, May 9th, 2026

View details for race Roxbury Road Race Series #10

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

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

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

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

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

WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

View details for race WeCare-Mother's Day 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

Mother's Day 5K

Yorktown Heights, NY

Sunday, May 10th, 2026

View details for race Mother's Day 5K

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

Roxbury Road Race Series #11

Roxbury, CT

Saturday, May 16th, 2026

View details for race Roxbury Road Race Series #11

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

View details for race Bailey's Garden 5K

RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

View details for race RESERVOIR RUSH

2026 CACNA1A 5K

Norwalk, CT

Saturday, May 16th, 2026

View details for race 2026 CACNA1A 5K

Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

View details for race Forgotten Forest 9 Hour Ultra

Your Way 5k - Ella Rose Foundation

New Windsor, NY

Saturday, May 16th, 2026

View details for race Your Way 5k - Ella Rose Foundation

Pleasantville 5K Run/Walk for Education

Pleasantville, NY

Saturday, May 16th, 2026

1 Mile

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

2nd Annual 5K Esopus Fire Department Run/Walk

Ulster Park, NY

Saturday, May 16th, 2026

View details for race 2nd Annual 5K Esopus Fire Department Run/Walk

Spring Into Spring Glen 5K

Hamden, CT

Sunday, May 17th, 2026

View details for race Spring Into Spring Glen 5K

"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

Annual 5K RUN & WALK With The DOGS

Beacon, NY

Sunday, May 17th, 2026

View details for race Annual 5K RUN & WALK With The DOGS

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

Guardian Revival 5K

Carmel, NY

Sunday, May 17th, 2026

View details for race Guardian Revival 5K

Newington Library 5K Challenge

Newington, CT

Sunday, May 17th, 2026

View details for race Newington Library 5K Challenge

Fleet Feet Poughkeepsie's 9th Annual Great Donu...

Poughkeepsie, NY

Sunday, May 17th, 2026

View details for race Fleet Feet Poughkeepsie's 9th Annual Great Donut Run Powered by ASICS

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

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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