Upcoming Races Near Middletown, CT in May, 2026

Name: Run the Vineyards - Memorial Day at Pindar 5K
Start: 2026-05-24
End: 2026-05-24
Location: Peconic

4th Annual Sail to the Finish 2M Run

Middlebury, CT

Saturday, May 2nd, 2026

Featured

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

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

Woodstock CT Marathon & Relay

Woodstock, CT

Saturday, May 2nd, 2026

Marathon

View details for race Woodstock CT Marathon & Relay

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

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

Brew Run

New London, CT

Saturday, May 2nd, 2026

1 Mile

View details for race Brew 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

Jack Rome Memorial 5K

Wilbraham, MA

Saturday, May 2nd, 2026

1 Mile

Fast

View details for race Jack Rome Memorial 5K

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

Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

View details for race Glenholme 5K Run For Autism

Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

Trail

Fast

View details for race Mount Archer Trail Race

Glenbrook Middle School Bulldog Dash

Longmeadow, MA

Sunday, May 3rd, 2026

View details for race Glenbrook Middle School Bulldog Dash

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

Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

View details for race Miles For Margaritas

Third Annual Race for Raymond

Hopkinton, RI

Sunday, May 3rd, 2026

View details for race Third Annual Race for Raymond

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

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

Roxbury Road Race Series #10

Roxbury, CT

Saturday, May 9th, 2026

View details for race Roxbury Road Race Series #10

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

Killingly Springtime Classic 5K

Danielson, CT

Saturday, May 9th, 2026

View details for race Killingly Springtime Classic 5K

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

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

Vernon Mothers Day Dash 5K

Vernon, CT

Sunday, May 10th, 2026

View details for race Vernon Mothers Day Dash 5K

WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

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

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

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

2026 CACNA1A 5K

Norwalk, CT

Saturday, May 16th, 2026

View details for race 2026 CACNA1A 5K

Camp Challenge

Ashford, CT

Saturday, May 16th, 2026

Trail

View details for race Camp Challenge

Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

View details for race Forgotten Forest 9 Hour Ultra

Newington Library 5K Challenge

Newington, CT

Sunday, May 17th, 2026

View details for race Newington Library 5K Challenge

Rossiter Run 2026

Washington Depot, CT

Sunday, May 17th, 2026

View details for race Rossiter Run 2026

Running Battles- A 5k"ish" Race To The Finish

Wolcott, CT

Sunday, May 17th, 2026

View details for race Running Battles- A 5k"ish" Race To The Finish

Spring Shuffle - Run, Walk, Roll!

Longmeadow, MA

Sunday, May 17th, 2026

View details for race 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

Strong Family Farm Chicken Run

Vernon, CT

Sunday, May 17th, 2026

View details for race Strong Family Farm Chicken Run

Tom McCoy Family Fun Run - Series

Westerly, RI

Wednesday, May 20th, 2026

View details for race Tom McCoy Family Fun Run - Series

32nd Annual | Weston Memorial Day Weekend 5K & ...

Weston, CT

Saturday, May 23rd, 2026

1 Mile

View details for race 32nd Annual | Weston Memorial Day Weekend 5K & Kids Fun Run

Roxbury Road Race Series #12

Roxbury, CT

Saturday, May 23rd, 2026

1 Mile

View details for race Roxbury Road Race Series #12

Savin Rock Waves of Hope

West Haven, CT

Saturday, May 23rd, 2026

View details for race Savin Rock Waves of Hope

RACE AROUND THE LAKE

New Hartford, CT

Sunday, May 24th, 2026

View details for race RACE AROUND THE LAKE

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

1 Mile

Trail

View details for race Run the Vineyards - Memorial Day at Pindar 5K

Explore more in Middletown, CT

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

Don't see your race? Add it!

Add Your Race (Free)