Upcoming 5K Races Near Middletown, CT

Name: Oh Boy 5K
Start: 2026-05-25
End: 2026-05-25
Location: Waterbury

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

Featured

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Brew Run

New London, CT

Saturday, May 2nd, 2026

1 Mile

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Jack Rome Memorial 5K

Wilbraham, MA

Saturday, May 2nd, 2026

1 Mile

Fast

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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

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

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

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Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

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Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

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Third Annual Race for Raymond

Hopkinton, RI

Sunday, May 3rd, 2026

View details for race Third Annual Race for Raymond

Sacandaga Sprint 5k

Northville, NY

Saturday, May 9th, 2026

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Sgt. Joshua D. Desforges Walk/Run Challenge

Ludlow, MA

Saturday, May 9th, 2026

Trail

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Baystate Health Nurses Week 5K Run/1K Walk

Holyoke, MA

Saturday, May 9th, 2026

View details for race Baystate Health Nurses Week 5K Run/1K Walk

Killingly Springtime Classic 5K

Danielson, CT

Saturday, May 9th, 2026

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Vernon Mothers Day Dash 5K

Vernon, CT

Sunday, May 10th, 2026

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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

WeCare-Mother's Day 5K

Brookfield, CT

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

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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Lauren's Haven 5K Run/ Walk

Springfield, MA

Saturday, May 16th, 2026

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Teacher vs Students 5K

Cromwell, CT

Saturday, May 16th, 2026

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End the Stigma: Mental Health Awareness 5K

New London, CT

Saturday, May 16th, 2026

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Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

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Bailey's Garden 5K

Lebanon, CT

Saturday, May 16th, 2026

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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

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

The Follow Natural Fitness Women's Health 5K

Bridgeport, CT

Sunday, May 17th, 2026

1 Mile

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Strong Family Farm Chicken Run

Vernon, CT

Sunday, May 17th, 2026

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Celebrate Kate 5k

Springfield, MA

Sunday, May 17th, 2026

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Newington Library 5K Challenge

Newington, CT

Sunday, May 17th, 2026

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Somers Summer Series

Somers, CT

Sunday, May 17th, 2026

Trail

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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!

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

Miles for Mary Run/Walk

Westfield, MA

Sunday, May 17th, 2026

1 Mile

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Spring Into Spring Glen 5K

Hamden, CT

Sunday, May 17th, 2026

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FreeFromEvil 5k Race/Walk

Waterbury, CT

Sunday, May 17th, 2026

View details for race FreeFromEvil 5k Race/Walk

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

Springfield, MA

Sunday, May 17th, 2026

1 Mile

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Tom McCoy Family Fun Run - Series

Westerly, RI

Wednesday, May 20th, 2026

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Get Smart for Wilton 5K

Wilton, CT

Friday, May 22nd, 2026

Fast

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North Stonington Education Foundation 5k and 2 ...

North Stonington, CT

Saturday, May 23rd, 2026

View details for race North Stonington Education Foundation 5k and 2 Mile Walk

5K Walk/Jog/Run for Jon

Woodbury, CT

Saturday, May 23rd, 2026

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Dustin L. Doyon Memorial Road Race

Suffield, CT

Saturday, May 23rd, 2026

10K

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Savin Rock Waves of Hope 5k

West Haven, CT

Saturday, May 23rd, 2026

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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

Marlborough Lions Club Round The Lake 5K

Marlborough, CT

Sunday, May 24th, 2026

View details for race Marlborough Lions Club Round The Lake 5K

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

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Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

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Explore more in Middletown, CT

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

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