Upcoming Races Near Pleasant Valley, NY in May, 2026

Name: 17th Annual Barkhamsted River Run 5K
Start: 2026-05-31
End: 2026-05-31
Location: Barkhamsted

4th Annual Sail to the Finish 2M Run

Middlebury, CT

Saturday, May 2nd, 2026

Featured

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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

Roxbury Road Race Series #9

Roxbury, CT

Saturday, May 2nd, 2026

View details for race Roxbury Road Race Series #9

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

Glenholme 5K Run For Autism

Washington Depot, CT

Sunday, May 3rd, 2026

Fast

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CTA Scholarship 5k Run/Walk

Carmel, NY

Sunday, May 3rd, 2026

Trail

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2026 Unified 5K - Montvale

Montvale, NJ

Sunday, May 3rd, 2026

1 Mile

View details for race 2026 Unified 5K - Montvale

Breast Cancer Alliance 5K for Hope

Greenwich, CT

Sunday, May 3rd, 2026

View details for race Breast Cancer Alliance 5K for Hope

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

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Safe Harbors of the Hudson Run/Walk 5K

Newburgh, NY

Saturday, May 9th, 2026

View details for race Safe Harbors of the Hudson Run/Walk 5K

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

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)

Mother's Day 5K

Yorktown Heights, NY

Sunday, May 10th, 2026

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WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

View details for race WeCare-Mother's Day 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

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

Pleasantville 5K Run/Walk for Education

Pleasantville, NY

Saturday, May 16th, 2026

1 Mile

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

2026 CACNA1A 5K

Norwalk, CT

Saturday, May 16th, 2026

View details for race 2026 CACNA1A 5K

Roxbury Road Race Series #11

Roxbury, CT

Saturday, May 16th, 2026

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Miles4Marcus

Mahwah, NJ

Saturday, May 16th, 2026

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Your Way 5k - Ella Rose Foundation

New Windsor, NY

Saturday, May 16th, 2026

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

2nd Annual 5K Esopus Fire Department Run/Walk

Ulster Park, NY

Saturday, May 16th, 2026

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MRCC/Trail Conference 5K

Mahwah, NJ

Sunday, May 17th, 2026

Trail

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Annual 5K RUN & WALK With The DOGS

Beacon, NY

Sunday, May 17th, 2026

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Guardian Revival 5K

Carmel, NY

Sunday, May 17th, 2026

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Run Like The Wind 5K

Ellenville, NY

Sunday, May 17th, 2026

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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

Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

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Book it! 2026

Hudson (Churchtown), NY

Sunday, May 17th, 2026

View details for race Book it! 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

2025 Weston CT Memorial Day Weekend 5K Road Race

Weston, CT

Saturday, May 23rd, 2026

1 Mile

View details for race 2025 Weston CT Memorial Day Weekend 5K Road Race

5K Walk/Jog/Run for Jon

Woodbury, CT

Saturday, May 23rd, 2026

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Kiwanis Club of Chester Annual 5K

Chester, NY

Saturday, May 23rd, 2026

View details for race Kiwanis Club of Chester Annual 5K

Roxbury Road Race Series #12

Roxbury, CT

Saturday, May 23rd, 2026

1 Mile

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RACE AROUND THE LAKE

New Hartford, CT

Sunday, May 24th, 2026

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Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

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Easton Memorial Day Mile Race

Easton, CT

Monday, May 25th, 2026

1 Mile

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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

View details for race Roxbury Road Race Series #13

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

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

Poughkeepsie, NY

Saturday, May 30th, 2026

Trail

View details for race Peach Hill "Run For the Hill of It" 5K

Bleu's Run for Rescue 5K

Washingtonville, NY

Sunday, May 31st, 2026

View details for race Bleu's Run for Rescue 5K

17th Annual Barkhamsted River Run 5K

Barkhamsted, CT

Sunday, May 31st, 2026

1 Mile

View details for race 17th Annual Barkhamsted River Run 5K

Explore more in Pleasant Valley, NY

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

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