Upcoming 5K Races Near Pleasant Valley, NY

Name: 33rd Annual Halloween 5K and Kids Fun Run
Start: 2026-10-18
End: 2026-10-18
Location: Brookfield

Town of Newburgh Post to Post Run for Veterans

Newburgh, NY

Saturday, November 8th, 2025

Featured

View details for race Town of Newburgh Post to Post Run for Veterans

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Honor Our Veterans 5k

Westport, CT

Tuesday, November 11th, 2025

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Sargent Elementary 5K Turkey Trot

Beacon, NY

Saturday, November 22nd, 2025

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Run for the Turkeys 5K Road Race

New Fairfield, CT

Sunday, November 23rd, 2025

View details for race Run for the Turkeys 5K Road Race

Head for the Hilltop 5K + Kids Fun Run

Yorktown Heights, NY

Sunday, November 23rd, 2025

Trail

View details for race Head for the Hilltop 5K + Kids Fun Run

New Canaan Turkey Trot

New Canaan, CT

Sunday, November 23rd, 2025

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Saint Stephen's CYO Basketball Turkey Trot

Warwick, NY

Thursday, November 27th, 2025

View details for race Saint Stephen's CYO Basketball Turkey Trot

Westchester Turkey Trot 10K & 5K

Valhalla, NY

Thursday, November 27th, 2025

10K

View details for race Westchester Turkey Trot 10K & 5K

Somers Track & Field Booster Club 7th Annual Th...

Somers, NY

Thursday, November 27th, 2025

1 Mile

View details for race Somers Track & Field Booster Club 7th Annual Thanksgiving Turkey Trot

The Cold Spring Turkey Trot

Cold Spring, NY

Thursday, November 27th, 2025

View details for race The Cold Spring Turkey Trot

14th Annual O'BRiley 5K Turkey Trot AT 9AM

Collinsville, CT

Thursday, November 27th, 2025

View details for race 14th Annual O'BRiley 5K Turkey Trot AT 9AM

Bethel Turkey Trot

Bethel, CT

Thursday, November 27th, 2025

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Newtown Turkey Trot

Newtown, CT

Thursday, November 27th, 2025

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Rhinebeck Ferncliff Forest 5k Turkey Trot

Rhinebeck, NY

Thursday, November 27th, 2025

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Rowayton Turkey Trot

Norwalk, CT

Thursday, November 27th, 2025

1 Mile

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The Joyce Allen Great Turkey Escape

Redding, CT

Thursday, November 27th, 2025

1 Mile

View details for race The Joyce Allen Great Turkey Escape

Boys & Girls Club of Ridgefield 44th Annual Tur...

Ridgefield, CT

Thursday, November 27th, 2025

1 Mile

View details for race Boys & Girls Club of Ridgefield 44th Annual Turkey Trot

Commodore Hull Thanksgiving Day 5k Road Race

Shelton, CT

Thursday, November 27th, 2025

View details for race Commodore Hull Thanksgiving Day 5k Road Race

2025 Woodstock Turkey Trot

Woodstock, NY

Thursday, November 27th, 2025

Fast

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2025 Southbury Turkey Trot 5K & Kids Fun Run

Southbury, CT

Thursday, November 27th, 2025

Fast

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Darien Depot Overstuffed Turkey Trot 5k and 1 M...

Darien, CT

Friday, November 28th, 2025

1 Mile

View details for race Darien Depot Overstuffed Turkey Trot 5k and 1 Mile Fun Run

Greenwich Alliance Turkey Trot 5K & 1 Mile Fun ...

Greenwich, CT

Saturday, November 29th, 2025

1 Mile

View details for race Greenwich Alliance Turkey Trot 5K & 1 Mile Fun Run/Walk

Run Santa Run

New Milford, CT

Saturday, November 29th, 2025

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Cow Chip Cross Country Run for the 33rd year!

Trumbull, CT

Saturday, November 29th, 2025

View details for race Cow Chip Cross Country Run for the 33rd year!

Fleet Feet Poughkeepsie's 2024 Grateful Gallop ...

Lagrangeville, NY

Saturday, November 29th, 2025

View details for race Fleet Feet Poughkeepsie's 2024 Grateful Gallop 5K to Benefit Dutchess Outreach

2025 NIA Jingle Bell Run - 37th Annual

Trumbull, CT

Saturday, December 6th, 2025

1 Mile

View details for race 2025 NIA Jingle Bell Run - 37th Annual

Santa Made Me Do It

Bethlehem, CT

Saturday, December 6th, 2025

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YMCA 41st Annual Reindeer Ramble

Kingston, NY

Sunday, December 7th, 2025

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Feeding 500 Holiday Hustle

Wilton, CT

Sunday, December 7th, 2025

View details for race Feeding 500 Holiday Hustle

11th Annual Tinsel Trot 5k Fun Run

Rock Hill, NY

Saturday, December 13th, 2025

View details for race 11th Annual Tinsel Trot 5k Fun Run

2nd Annual HV Hawks 5K Reindeer Dash and Fun Run

Washingtonville, NY

Saturday, December 13th, 2025

View details for race 2nd Annual HV Hawks 5K Reindeer Dash and Fun Run

2025 Jingle Bell Run - Westchester, NY

Purchase, NY

Saturday, December 13th, 2025

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

BPT PAL Christmas Village Road Race

Trumbull, CT

Saturday, December 13th, 2025

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Frozen RexTacular 5K

New City, NY

Saturday, December 13th, 2025

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2025 Norwalk Jingle Bell 5K

Norwalk, CT

Saturday, December 13th, 2025

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New Canaan Santa Run 2025

New Canaan, CT

Saturday, December 20th, 2025

1 Mile

View details for race New Canaan Santa Run 2025

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

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

NVCC Food Pantry Run/Walk

Waterbury, CT

Sunday, March 29th, 2026

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John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

Trail

View details for race John Jay Community Trail Race

Brooklyn Cider House Spiked Apple 5k

New Paltz, NY

Sunday, April 19th, 2026

View details for race Brooklyn Cider House Spiked Apple 5k

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

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

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

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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

2026 Independence Series - Day 5 (NY)

Montgomery, NY

Sunday, June 7th, 2026

Half

Marathon

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

Murray Lender 5K Bagel Run

Woodbridge, CT

Sunday, September 20th, 2026

View details for race Murray Lender 5K Bagel Run

2025 Pies & Pub TaTa Trot 5k

Middlebury, CT

Saturday, September 26th, 2026

View details for race 2025 Pies & Pub TaTa Trot 5k

33rd Annual Halloween 5K and Kids Fun Run

Brookfield, CT

Sunday, October 18th, 2026

View details for race 33rd Annual Halloween 5K and Kids Fun Run

Explore more in Pleasant Valley, NY

Distances:

5K 10K Half Marathon Marathon

Months:

November December January

Tags:

Trail Boston Qualifiers Fast Courses

State:

All New York races

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