Upcoming Races Near Poughkeepsie, NY in May, 2026

Name: Catskill Spring Rush & 5K
Start: 2026-05-30
End: 2026-05-30
Location: Catskill

A Run to Remember

Red Hook, NY

Saturday, May 2nd, 2026

Featured

10K

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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

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

The Elephant Run

Park Ridge, NJ

Sunday, May 3rd, 2026

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Elephant Run 5K

Park Ridge, NJ

Sunday, May 3rd, 2026

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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

32nd Annual Delaware River 5k Run/Walk

Port Jervis, NY

Sunday, May 3rd, 2026

View details for race 32nd Annual Delaware River 5k Run/Walk

Hastings Color Run

Hastings On Hudson, NY

Sunday, May 3rd, 2026

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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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ViK 5K

Wantage, NJ

Sunday, May 3rd, 2026

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

Waldwick, NJ

Sunday, May 3rd, 2026

1 Mile

Fast

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2026 Unified 5K - Montvale

Montvale, NJ

Sunday, May 3rd, 2026

1 Mile

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Virtual Run Like A Mother 5k & Kids 1 Mile

Ridgefield, CT

Thursday, May 7th, 2026

1 Mile

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Piermont Fire 5K

Piermont, NY

Saturday, May 9th, 2026

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Safe Harbors of the Hudson 5K

Newburgh, NY

Saturday, May 9th, 2026

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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

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)

Roxbury Road Race Series #10

Roxbury, CT

Saturday, May 9th, 2026

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Run Like a Mother 5K and Kid's 1-Mile 2026

Ridgefield, CT

Sunday, May 10th, 2026

1 Mile

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WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

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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

Miles4Marcus

Mahwah, NJ

Saturday, May 16th, 2026

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Your Way 5k - Ella Rose Foundation

New Windsor, NY

Saturday, May 16th, 2026

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Roxbury Road Race Series #11

Roxbury, CT

Saturday, May 16th, 2026

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Pleasantville 5K Run/Walk for Education

Pleasantville, NY

Saturday, May 16th, 2026

1 Mile

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2026 CACNA1A 5K

Norwalk, CT

Saturday, May 16th, 2026

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2nd Annual 5K Esopus Fire Department Run/Walk

Ulster Park, NY

Saturday, May 16th, 2026

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Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

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Friends of TJ 5K Fun Run

Wyckoff, NJ

Sunday, May 17th, 2026

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

Wolcott, CT

Sunday, May 17th, 2026

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Book it! 2026

Hudson (Churchtown), NY

Sunday, May 17th, 2026

View details for race Book it! 2026

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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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

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Guardian Revival 5K

Carmel, NY

Sunday, May 17th, 2026

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Roxbury Road Race Series #12

Roxbury, CT

Saturday, May 23rd, 2026

1 Mile

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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

Mount 5K and Fun Run 2026

Esopus, NY

Saturday, May 23rd, 2026

1 Mile

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5K Walk/Jog/Run for Jon

Woodbury, CT

Saturday, May 23rd, 2026

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Koinonia 5K

Highland Lake, NY

Saturday, May 23rd, 2026

Trail

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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

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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Explore more in Poughkeepsie, NY

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

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