Upcoming 5K Races Near Pawling, NY

Name: 2026 Independence Series - Day 5 (NY)
Start: 2026-06-07
End: 2026-06-07
Location: Montgomery

Fleet Feet Poughkeepsie's 2025 Ugly Sweater Run

Poughkeepsie, NY

Sunday, December 7th, 2025

Featured

View details for race Fleet Feet Poughkeepsie's 2025 Ugly Sweater Run

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YMCA 41st Annual Reindeer Ramble

Kingston, NY

Sunday, December 7th, 2025

View details for race YMCA 41st Annual Reindeer Ramble

Christopher Martin's Christmas Run for Children

New Haven, CT

Sunday, December 7th, 2025

View details for race Christopher Martin's Christmas Run for Children

CLA Blue Back Mitten Run

West Hartford, CT

Sunday, December 7th, 2025

View details for race CLA Blue Back Mitten Run

Feeding 500 Holiday Hustle

Wilton, CT

Sunday, December 7th, 2025

View details for race Feeding 500 Holiday Hustle

2025 Jingle Bell Run - Westchester, NY

Purchase, NY

Saturday, December 13th, 2025

View details for race 2025 Jingle Bell Run - Westchester, NY

3rd Annual HV Hawks 5K Reindeer Dash and Fun Run

Washingtonville, NY

Saturday, December 13th, 2025

View details for race 3rd Annual HV Hawks 5K Reindeer Dash and Fun Run

2025 Norwalk Jingle Bell 5K

Norwalk, CT

Saturday, December 13th, 2025

View details for race 2025 Norwalk Jingle Bell 5K

BPT PAL Christmas Village Road Race

Trumbull, CT

Saturday, December 13th, 2025

View details for race BPT PAL Christmas Village Road Race

Frozen RexTacular 5K

New City, NY

Saturday, December 13th, 2025

View details for race Frozen RexTacular 5K

Meals On Wheels Frosty 5K

Scarsdale, NY

Sunday, December 14th, 2025

View details for race Meals On Wheels Frosty 5K

Dobbs Ferry Holiday Hustle 5k & KIDS Reindeer ...

Dobbs Ferry, NY

Sunday, December 14th, 2025

View details for race Dobbs Ferry Holiday Hustle 5k & KIDS Reindeer Fun Run

The Holiday Run & Walk For Toys

Stratford, CT

Sunday, December 14th, 2025

View details for race The Holiday Run & Walk For Toys

New Canaan Santa Run 2025

New Canaan, CT

Saturday, December 20th, 2025

1 Mile

View details for race New Canaan Santa Run 2025

Battle for Burnett

Fairfield, CT

Sunday, December 21st, 2025

View details for race Battle for Burnett

Snowflake 5K Run/Walk - Nyack Community Ambulan...

Nyack, NY

Sunday, December 28th, 2025

View details for race Snowflake 5K Run/Walk - Nyack Community Ambulance Corps

Chilly Chili Run

Orange, CT

Thursday, January 1st, 2026

View details for race Chilly Chili Run

Fleet Feet Hartford Winter 2026 Training Programs

West Hartford, CT

Saturday, January 3rd, 2026

10K

View details for race Fleet Feet Hartford Winter 2026 Training Programs

MADD Dry 5K

Fairfield, CT

Sunday, January 4th, 2026

View details for race MADD Dry 5K

Racefaster through the Mall - Garden State Plaz...

Paramus, NJ

Sunday, January 25th, 2026

View details for race Racefaster through the Mall - Garden State Plaza, Paramus

IRIS Run for Refugees

New Haven, CT

Sunday, February 8th, 2026

View details for race IRIS Run for Refugees

SUPER SUNDAY 5K AND 2K PUP STRUT

Franklin Lakes, NJ

Sunday, February 8th, 2026

View details for race SUPER SUNDAY 5K AND 2K PUP STRUT

Cupid's Chase 5K Glen Rock

Glen Rock, NJ

Saturday, February 14th, 2026

View details for race Cupid's Chase 5K Glen Rock

99.1PLR CrossPoint Federal Credit Union ShamRoc...

New Haven, CT

Sunday, March 1st, 2026

View details for race 99.1PLR CrossPoint Federal Credit Union ShamRock & Roll 5K

ALS Crusaders 5k

White Plains, NY

Sunday, March 8th, 2026

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EDRRC - St. Patrick's 5K Run/Walk

Dover Plains, NY

Saturday, March 14th, 2026

View details for race EDRRC - St. Patrick's 5K Run/Walk

Run For Tomorrow

Northvale, NJ

Saturday, March 21st, 2026

1 Mile

View details for race Run For Tomorrow

Annual Johnny's Jog for Charity 5K - Blue Back ...

West Hartford, CT

Sunday, March 22nd, 2026

View details for race Annual Johnny's Jog for Charity 5K - Blue Back Square, West Hartford

Beach Bunny 5K

Fairfield, CT

Saturday, March 28th, 2026

View details for race Beach Bunny 5K

NVCC Food Pantry Run/Walk

Waterbury, CT

Sunday, March 29th, 2026

View details for race NVCC Food Pantry Run/Walk

John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

Trail

View details for race John Jay Community Trail Race

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

Trail

Fast

View details for race Ion Bank Cheshire Road Races

Farm & Forest All- Terrain 5K & Hog Wild Kids F...

Stamford, CT

Sunday, April 12th, 2026

View details for race Farm & Forest All- Terrain 5K & Hog Wild Kids Fun Run

Race for YOUR Mental Health

Meriden, CT

Saturday, April 18th, 2026

View details for race Race for YOUR Mental Health

Brooklyn Cider House Spiked Apple 5k

New Paltz, NY

Sunday, April 19th, 2026

View details for race Brooklyn Cider House Spiked Apple 5k

Gilbert Joseph & Brian Annual 5K (Gilbert JBA5K)

Winsted, CT

Saturday, April 25th, 2026

View details for race Gilbert Joseph & Brian Annual 5K (Gilbert JBA5K)

River Edge Run

River Edge, NJ

Saturday, April 25th, 2026

1 Mile

View details for race River Edge Run

Deacon Chuck Dietsch Memorial 5K Run & Walk for...

Southbury, CT

Saturday, April 25th, 2026

View details for race Deacon Chuck Dietsch Memorial 5K Run & Walk for Haiti

A Run to Remember

Red Hook, NY

Saturday, May 2nd, 2026

10K

Trail

View details for race A Run to Remember

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

WeCare-Mother's Day 5K

Brookfield, CT

Sunday, May 10th, 2026

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

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

Run Like The Wind 5K

Ellenville, NY

Sunday, May 17th, 2026

View details for race Run Like The Wind 5K

Demarest 5K

Demarest, NJ

Sunday, May 17th, 2026

View details for race Demarest 5K

MRCC/Trail Conference 5K

Mahwah, NJ

Sunday, May 17th, 2026

Trail

View details for race MRCC/Trail Conference 5K

Kiwanis Club of Chester Annual 5K

Chester, NY

Saturday, May 23rd, 2026

View details for race Kiwanis Club of Chester Annual 5K

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

Trail

Fast

View details for race Oh Boy 5K

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

Athletic Brewing Company Fairfield Road Races

Fairfield, CT

Saturday, June 6th, 2026

Half

10K

View details for race Athletic Brewing Company Fairfield Road Races

2026 Independence Series - Day 5 (NY)

Montgomery, NY

Sunday, June 7th, 2026

Half

Marathon

View details for race 2026 Independence Series - Day 5 (NY)

Explore more in Pawling, NY

Distances:

5K 10K Half Marathon Marathon

Months:

December January February

Tags:

Trail Boston Qualifiers Fast Courses

State:

All New York races

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