Upcoming Races Near Old Saybrook, CT in May, 2026

Name: Run the Vineyards - Jonathan Edwards 5K
Start: 2026-05-31
End: 2026-05-31
Location: North Stonington

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

Hartford, CT

Saturday, May 2nd, 2026

Featured

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

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Woodstock CT Marathon & Relay

Woodstock, CT

Saturday, May 2nd, 2026

Marathon

View details for race Woodstock CT Marathon & Relay

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

St.Mary-St.Michael School 1 Mile Run

Derby, CT

Saturday, May 2nd, 2026

1 Mile

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Brew Run

New London, CT

Saturday, May 2nd, 2026

1 Mile

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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

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

Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

View details for race Miles For Margaritas

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

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

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

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

Saint James, NY

Saturday, May 9th, 2026

View details for race St. James 5 Mile Challenge and 5K Fun Run/Walk

Killingly Springtime Classic 5K

Danielson, CT

Saturday, May 9th, 2026

View details for race Killingly Springtime Classic 5K

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

Vernon Mothers Day Dash 5K

Vernon, CT

Sunday, May 10th, 2026

View details for race Vernon Mothers Day Dash 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

Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

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RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

View details for race RESERVOIR RUSH

Forgotten Forest 9 Hour Ultra

Stratford, 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

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

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

Running Battles- A 5kish Race To The Finish

Wolcott, CT

Sunday, May 17th, 2026

View details for race Running Battles- A 5kish Race To The Finish

"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

Tom McCoy Family Fun Run - Series

Westerly, RI

Wednesday, May 20th, 2026

View details for race Tom McCoy Family Fun Run - Series

5K Walk/Jog/Run for Jon

Woodbury, CT

Saturday, May 23rd, 2026

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

Savin Rock Waves of Hope

West Haven, CT

Saturday, May 23rd, 2026

View details for race Savin Rock Waves of Hope

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

1 Mile

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Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

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Woodstock Memorial Day 5K & 10K

Woodstock, CT

Monday, May 25th, 2026

10K

View details for race Woodstock Memorial Day 5K & 10K

Easton Memorial Day Mile Race

Easton, CT

Monday, May 25th, 2026

1 Mile

View details for race Easton Memorial Day Mile Race

Meriden Memorial Mile

Meriden, CT

Monday, May 25th, 2026

1 Mile

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PFC JOSEPH P DWYER PTSD MEMORIAL 5K RUN

Rocky Point, NY

Saturday, May 30th, 2026

View details for race PFC JOSEPH P DWYER PTSD MEMORIAL 5K RUN

Spring Street Mile & 5K Presented by PTSMC

Manchester, CT

Saturday, May 30th, 2026

1 Mile

Fast

View details for race Spring Street Mile & 5K Presented by PTSMC

The River Run 5K and Kids Fun Run

Old Saybrook, CT

Saturday, May 30th, 2026

1 Mile

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Woodland Ramble Trail Run

Mystic, CT

Saturday, May 30th, 2026

Trail

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The Joe Keany Memorial 5K and 1 Mile Fun Run

Miller Place, NY

Sunday, May 31st, 2026

1 Mile

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Run the Vineyards - Jonathan Edwards 5K

North Stonington, CT

Sunday, May 31st, 2026

View details for race Run the Vineyards - Jonathan Edwards 5K

Explore more in Old Saybrook, CT

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

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