Upcoming Races Near Winsted, CT

Name: Peach Hill "Run For the Hill of It" 5K
Start: 2026-05-30
End: 2026-05-30
Location: Poughkeepsie

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

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Sgt. Joshua D. Desforges Walk/Run Challenge

Ludlow, MA

Saturday, May 9th, 2026

Trail

View details for race Sgt. Joshua D. Desforges Walk/Run Challenge

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

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

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

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

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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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

Roxbury Road Race Series #11

Roxbury, CT

Saturday, May 16th, 2026

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RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

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Teacher vs Students 5K

Cromwell, CT

Saturday, May 16th, 2026

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Bailey's Garden 5K

Lebanon, CT

Saturday, May 16th, 2026

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Dan the Man 5K Run/Walk for ALS

Berlin, CT

Saturday, May 16th, 2026

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Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

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Lauren's Haven 5K Run/ Walk

Springfield, MA

Saturday, May 16th, 2026

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Running Battles- A Race To The Finish

Wolcott, CT

Sunday, May 17th, 2026

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

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

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Strong Family Farm Chicken Run

Vernon, CT

Sunday, May 17th, 2026

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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

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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Book it! 2026

Hudson (Churchtown), NY

Sunday, May 17th, 2026

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Guardian Revival 5K

Carmel, NY

Sunday, May 17th, 2026

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Miles for Mary Run/Walk

Westfield, MA

Sunday, May 17th, 2026

1 Mile

View details for race Miles for Mary Run/Walk

Franklin Academy 6th Annual Double Helix 1.75 M...

East Haddam, CT

Sunday, May 17th, 2026

View details for race Franklin Academy 6th Annual Double Helix 1.75 Mile Race

Spring Shuffle - Run, Walk, Roll!

Longmeadow, MA

Sunday, May 17th, 2026

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

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

Springfield, MA

Sunday, May 17th, 2026

1 Mile

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Somers Summer Series

Somers, CT

Sunday, May 17th, 2026

Trail

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2026 Rossiter Run 5K Race and Fun Run/Walk

Washington Depot, CT

Sunday, May 17th, 2026

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Dustin L. Doyon Memorial Road Race

Suffield, CT

Saturday, May 23rd, 2026

10K

View details for race Dustin L. Doyon Memorial Road Race

Mount 5K and Fun Run 2026

Esopus, NY

Saturday, May 23rd, 2026

1 Mile

View details for race Mount 5K and Fun Run 2026

Savin Rock Waves of Hope

West Haven, CT

Saturday, May 23rd, 2026

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2nd Annual Memorial Day 5K

Ware, MA

Saturday, May 23rd, 2026

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5K Walk/Jog/Run for Jon

Woodbury, CT

Saturday, May 23rd, 2026

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Roxbury Road Race Series #12

Roxbury, CT

Saturday, May 23rd, 2026

1 Mile

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Marlborough Lions Club Round The Lake 5K

Marlborough, CT

Sunday, May 24th, 2026

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

RACE AROUND THE LAKE

New Hartford, CT

Sunday, May 24th, 2026

View details for race RACE AROUND THE LAKE

Norfolk VFD 5-Mile Road Race

Norfolk, CT

Monday, May 25th, 2026

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Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

Fast

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Easton Memorial Day Mile Race

Easton, CT

Monday, May 25th, 2026

1 Mile

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Meriden Memorial Mile

Meriden, CT

Monday, May 25th, 2026

1 Mile

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Catskill Spring Rush & Sprint 5K

Catskill, NY

Saturday, May 30th, 2026

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Catskill Spring Rush & 5K

Catskill, NY

Saturday, May 30th, 2026

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Roxbury Road Race Series #13

Roxbury, CT

Saturday, May 30th, 2026

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EDRRC - Eagle Run 5K Run/Walk and Kids Run

Clinton Corners, NY

Saturday, May 30th, 2026

View details for race EDRRC - Eagle Run 5K Run/Walk and Kids Run

Spring Street Mile & 5K Presented by PTSMC

Manchester, CT

Saturday, May 30th, 2026

1 Mile

Fast

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Peach Hill "Run For the Hill of It" 5K

Poughkeepsie, NY

Saturday, May 30th, 2026

Trail

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Explore more in Winsted, CT

Distances:

5K 10K Half Marathon Marathon

Months:

May June July

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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