Upcoming Races Near Pawling, NY in May, 2026

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

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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FISHKILL FREEDOM 5K FESTIVAL & 1 MI FUN RUN

Fishkill, NY

Saturday, May 2nd, 2026

View details for race FISHKILL FREEDOM 5K FESTIVAL & 1 MI FUN RUN

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

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

A Run to Remember

Red Hook, NY

Saturday, May 2nd, 2026

10K

View details for race A Run to Remember

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

Roxbury Road Race Series #9

Roxbury, CT

Saturday, May 2nd, 2026

View details for race Roxbury Road Race Series #9

Miles For Margaritas

Stratford, CT

Sunday, May 3rd, 2026

1 Mile

View details for race Miles For Margaritas

2026 Unified 5K - Montvale

Montvale, NJ

Sunday, May 3rd, 2026

1 Mile

View details for race 2026 Unified 5K - Montvale

Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

View details for race Glenholme 5K Run For Autism

Breast Cancer Alliance 2025 5K for Hope Run/Walk

Greenwich, CT

Sunday, May 3rd, 2026

View details for race Breast Cancer Alliance 2025 5K for Hope Run/Walk

CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

View details for race CTA Scholarship 5k Run/Walk

Waldwick Chamber of Commerce 5K Run and 1 Mile ...

Waldwick, NJ

Sunday, May 3rd, 2026

1 Mile

Fast

View details for race Waldwick Chamber of Commerce 5K Run and 1 Mile Walk

The Elephant Run

Park Ridge, NJ

Sunday, May 3rd, 2026

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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

Roxbury Road Race Series #10

Roxbury, CT

Saturday, May 9th, 2026

View details for race Roxbury Road Race Series #10

Piermont Fire 5K

Piermont, NY

Saturday, May 9th, 2026

View details for race Piermont Fire 5K

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

RPEF Sprint for Our Schools 5K & Family Fun Run

Ramsey, NJ

Saturday, May 9th, 2026

1 Mile

View details for race RPEF Sprint for Our Schools 5K & Family Fun Run

Safe Harbors of the Hudson 5K

Newburgh, NY

Saturday, May 9th, 2026

View details for race Safe Harbors of the Hudson 5K

The Charlie Goldberger Loucks 5K Presented by T...

White Plains, NY

Saturday, May 9th, 2026

View details for race The Charlie Goldberger Loucks 5K Presented by The Loucks Games and The White Plains Rotary

Bruynswick Winery Run for UCSPCA XC 6K (3.6 mile)

Gardiner, NY

Saturday, May 9th, 2026

View details for race Bruynswick Winery Run for UCSPCA XC 6K (3.6 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

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

Rubin Run

Tenafly, NJ

Sunday, May 10th, 2026

10K

1 Mile

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Mother's Day 5K

Yorktown Heights, NY

Sunday, May 10th, 2026

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Stamford Boys & Girls Club Corporate 5K at Mill...

Stamford, CT

Thursday, May 14th, 2026

View details for race Stamford Boys & Girls Club Corporate 5K at Mill River Park

Your Way 5k - Ella Rose Foundation

New Windsor, NY

Saturday, May 16th, 2026

View details for race Your Way 5k - Ella Rose Foundation

Roxbury Road Race Series #11

Roxbury, CT

Saturday, May 16th, 2026

View details for race Roxbury Road Race Series #11

Forgotten Forest 9 Hour Ultra

Stratford, CT

Saturday, May 16th, 2026

Trail

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2nd Annual 5K Esopus Fire Department Run/Walk

Ulster Park, NY

Saturday, May 16th, 2026

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2026 CACNA1A 5K

Norwalk, CT

Saturday, May 16th, 2026

View details for race 2026 CACNA1A 5K

Pleasantville 5K Run/Walk for Education

Pleasantville, NY

Saturday, May 16th, 2026

1 Mile

View details for race Pleasantville 5K Run/Walk for Education

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

Miles4Marcus

Mahwah, NJ

Saturday, May 16th, 2026

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Demarest 5K

Demarest, NJ

Sunday, May 17th, 2026

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Newington Library 5K Challenge

Newington, CT

Sunday, May 17th, 2026

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Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

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MRCC/Trail Conference 5K

Mahwah, NJ

Sunday, May 17th, 2026

View details for race MRCC/Trail Conference 5K

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

Run Like The Wind 5K

Ellenville, NY

Sunday, May 17th, 2026

View details for race Run Like The Wind 5K

Friends of TJ 5K Fun Run

Wyckoff, NJ

Sunday, May 17th, 2026

View details for race Friends of TJ 5K Fun Run

Annual 5K RUN & WALK With The DOGS

Beacon, NY

Sunday, May 17th, 2026

View details for race Annual 5K RUN & WALK With The DOGS

Running Battles- A Race To The Finish

Wolcott, CT

Sunday, May 17th, 2026

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

Guardian Revival 5k

Carmel, NY

Sunday, May 17th, 2026

View details for race Guardian Revival 5k

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

5K Walk/Jog/Run for Jon

Woodbury, CT

Saturday, May 23rd, 2026

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

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 Pawling, NY

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

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