Upcoming 5K Races Near Highland, NY

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

Janis Rocco Football 5k Run/Walk

Oakland, NJ

Saturday, November 8th, 2025

Featured

View details for race Janis Rocco Football 5k Run/Walk

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Town of Newburgh Post to Post Run for Veterans

Newburgh, NY

Saturday, November 8th, 2025

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

Tappan Fire 5K Run/Walk

Tappan, NY

Sunday, November 9th, 2025

View details for race Tappan Fire 5K Run/Walk

Sargent Elementary 5K Turkey Trot

Beacon, NY

Saturday, November 22nd, 2025

View details for race Sargent Elementary 5K Turkey Trot

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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Run for the Turkeys 5K Road Race and Health Walk

New Fairfield, CT

Sunday, November 23rd, 2025

View details for race Run for the Turkeys 5K Road Race and Health Walk

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

2025 Southbury Turkey Trot 5K & Kids Fun Run

Southbury, CT

Thursday, November 27th, 2025

Fast

View details for race 2025 Southbury Turkey Trot 5K & Kids Fun Run

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

Rhinebeck Ferncliff Forest 5k Turkey Trot

Rhinebeck, NY

Thursday, November 27th, 2025

View details for race Rhinebeck Ferncliff Forest 5k Turkey Trot

The Joyce Allen Great Turkey Escape

Redding, CT

Thursday, November 27th, 2025

1 Mile

View details for race The Joyce Allen Great Turkey Escape

Bethel Turkey Trot

Bethel, CT

Thursday, November 27th, 2025

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2025 Woodstock Turkey Trot

Woodstock, NY

Thursday, November 27th, 2025

Fast

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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 presented by N...

Valhalla, NY

Thursday, November 27th, 2025

10K

View details for race Westchester Turkey Trot 10K & 5K presented by Northwell Orthopedics

Newtown Turkey Trot

Newtown, CT

Thursday, November 27th, 2025

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The Cold Spring Turkey Trot

Cold Spring, NY

Thursday, November 27th, 2025

View details for race The Cold Spring Turkey Trot

2025 River Vale Run 4 the Love and Fitness with...

River Vale, NJ

Thursday, November 27th, 2025

View details for race 2025 River Vale Run 4 the Love and Fitness with Friends Turkey Trot Charity 5K

Vernon Annual Thanksgiving Day Turkey Trot

Sussex, NJ

Thursday, November 27th, 2025

View details for race Vernon Annual Thanksgiving Day Turkey Trot

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

Fleet Feet Poughkeepsie's 2025 Grateful Gallop ...

Lagrangeville, NY

Saturday, November 29th, 2025

Fast

View details for race Fleet Feet Poughkeepsie's 2025 Grateful Gallop 5K to Benefit Dutchess Outreach

Run Santa Run

New Milford, CT

Saturday, November 29th, 2025

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Home Pro Exteriors Livingston Manor Turkey "Tro...

Livingston Manor, NY

Saturday, November 29th, 2025

View details for race Home Pro Exteriors Livingston Manor Turkey "Trout" 5K Run/Walk

Santa Made Me Do It

Bethlehem, CT

Saturday, December 6th, 2025

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Feeding 500 Holiday Hustle

Wilton, CT

Sunday, December 7th, 2025

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YMCA 41st Annual Reindeer Ramble

Kingston, NY

Sunday, December 7th, 2025

View details for race YMCA 41st Annual Reindeer Ramble

Fleet Feet Poughkeepsie's 2025 Ugly Sweater Run

Poughkeepsie, NY

Sunday, December 7th, 2025

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

2025 Jingle Bell Run - Westchester, NY

Purchase, NY

Saturday, December 13th, 2025

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

Frozen RexTacular 5K

New City, NY

Saturday, December 13th, 2025

View details for race Frozen RexTacular 5K

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

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

Dobbs Ferry Holiday Hustle 5k & Reindeer Fun Run

Dobbs Ferry, NY

Sunday, December 14th, 2025

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

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

YETI OR NOT Snowshoe Invasion

Vernon, NJ

Saturday, January 31st, 2026

1 Mile

View details for race YETI OR NOT Snowshoe Invasion

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

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

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

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

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 4 (NJ)

Sussex, NJ

Saturday, June 6th, 2026

Half

10K

View details for race 2026 Independence Series - Day 4 (NJ)

2026 Independence Series - Day 5 (NY)

Montgomery, NY

Sunday, June 7th, 2026

Half

Marathon

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

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 Highland, 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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