Upcoming Races Near Winsted, CT in May, 2026

Name: Roxbury Road Race Series #12
Start: 2026-05-23
End: 2026-05-23
Location: Roxbury

Jack Rome Memorial 5K

Wilbraham, MA

Saturday, May 2nd, 2026

Featured

1 Mile

Fast

View details for race Jack Rome Memorial 5K

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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

A Run to Remember

Red Hook, NY

Saturday, May 2nd, 2026

10K

View details for race A Run to Remember

Seven Sisters Trail Race Charity Bibs

Amherst, MA

Saturday, May 2nd, 2026

Trail

View details for race Seven Sisters Trail Race Charity Bibs

Roxbury Road Race Series #9

Roxbury, CT

Saturday, May 2nd, 2026

View details for race Roxbury Road Race Series #9

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

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

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

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

Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

View details for race Glenholme 5K Run For Autism

Dandelion Dash and Mushroom Mile

Hadley, MA

Sunday, May 3rd, 2026

1 Mile

Trail

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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

Runway 5K

Northampton, MA

Sunday, May 3rd, 2026

View details for race Runway 5K

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

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

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

Sgt. Joshua D. Desforges Walk/Run Challenge

Ludlow, MA

Saturday, May 9th, 2026

Trail

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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

Roxbury Road Race Series #10

Roxbury, CT

Saturday, May 9th, 2026

View details for race Roxbury Road Race Series #10

WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

View details for race WeCare-Mother's Day 5K

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

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

Lauren's Haven 5K Run/ Walk

Springfield, MA

Saturday, May 16th, 2026

View details for race Lauren's Haven 5K Run/ Walk

RESERVOIR RUSH

Moodus, CT

Saturday, May 16th, 2026

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Roxbury Road Race Series #11

Roxbury, CT

Saturday, May 16th, 2026

View details for race Roxbury Road Race Series #11

Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

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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

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

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

Rossiter Run 2026

Washington Depot, CT

Sunday, May 17th, 2026

View details for race Rossiter Run 2026

Running Battles- A Race To The Finish

Wolcott, CT

Sunday, May 17th, 2026

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

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!

Celebrate Kate 5k

Springfield, MA

Sunday, May 17th, 2026

View details for race Celebrate Kate 5k

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

Springfield, MA

Sunday, May 17th, 2026

1 Mile

View details for race Outrun Hunger 5K race - and 1-mile fun walk

Miles for Mary Run/Walk

Westfield, MA

Sunday, May 17th, 2026

1 Mile

View details for race Miles for Mary Run/Walk

Guardian Revival 5k

Carmel, NY

Sunday, May 17th, 2026

View details for race Guardian Revival 5k

Book it! 2026

Hudson (Churchtown), NY

Sunday, May 17th, 2026

View details for race Book it! 2026

2nd Annual Memorial Day 5K

Ware, MA

Saturday, May 23rd, 2026

View details for race 2nd Annual Memorial Day 5K

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

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

Roxbury Road Race Series #12

Roxbury, CT

Saturday, May 23rd, 2026

1 Mile

View details for race Roxbury Road Race Series #12

Explore more in Winsted, CT

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

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