Upcoming 5K Races Near Pleasant Valley, NY

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I RUN BEACON 5K RUN/WALK 2026

Beacon, NY

Sunday, September 20th, 2026

View details for race I RUN BEACON 5K RUN/WALK 2026

Circle of Care's Annual Walk/Run for Kids With ...

Westport, CT

Sunday, September 20th, 2026

View details for race Circle of Care's Annual Walk/Run for Kids With Cancer

MKFD FIRED UP 5K

Mount Kisco, NY

Sunday, September 20th, 2026

View details for race MKFD FIRED UP 5K

2025 Pies & Pub TaTa Trot 5k

Middlebury, CT

Saturday, September 26th, 2026

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

Woodbridge 5k

Woodbridge, CT

Saturday, September 26th, 2026

Fast

View details for race Woodbridge 5k

2026 Rhinebeck Fall Foliage Half Marathon & 5K

Rhinebeck, NY

Saturday, September 26th, 2026

Half

Fast

View details for race 2026 Rhinebeck Fall Foliage Half Marathon & 5K

Nicky Cass 5k Challenge

Congers, NY

Saturday, September 26th, 2026

View details for race Nicky Cass 5k Challenge

Hayfield Hustle and Oktoberfest at New Pond Farm

Redding, CT

Saturday, September 26th, 2026

View details for race Hayfield Hustle and Oktoberfest at New Pond Farm

South Orange Family Annual 5k & Kids Color Dash

Monroe, NY

Saturday, September 26th, 2026

View details for race South Orange Family Annual 5k & Kids Color Dash

Dylan Dainack Memorial 5k

Liberty, NY

Saturday, September 26th, 2026

View details for race Dylan Dainack Memorial 5k

Roxbury Road Race Series #28

Roxbury, CT

Saturday, September 26th, 2026

View details for race Roxbury Road Race Series #28

4th Annual Beach to Beach 5k

Morris, CT

Sunday, September 27th, 2026

Fast

View details for race 4th Annual Beach to Beach 5k

Pounding the Pavement for Pink Races

Seymour, CT

Friday, October 2nd, 2026

1 Mile

View details for race Pounding the Pavement for Pink Races

Sugar Loaf 5K

Chester, NY

Saturday, October 3rd, 2026

View details for race Sugar Loaf 5K

Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Apple Harvest Road Races

48th Annual Kelly Memorial Police Chase

Campbell Hall, NY

Sunday, October 4th, 2026

10K

View details for race 48th Annual Kelly Memorial Police Chase

Empire State Half Marathon & 5k

Congers, NY

Sunday, October 4th, 2026

Half

10K

View details for race Empire State Half Marathon & 5k

Norfolk Land Trust Trail Race Series/Haystack M...

Norfolk, CT

Sunday, October 4th, 2026

10K

Half

Trail

View details for race Norfolk Land Trust Trail Race Series/Haystack Mountain Challenge

RACE FOR CATHERINE

Newtown, CT

Friday, October 9th, 2026

View details for race RACE FOR CATHERINE

Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 2026

1 Mile

Trail

View details for race Gemstone Sparkle Sprint 5k

Obstacle Wonderland Hallo-Weird 4 "Relish the C...

Wallkill, NY

Sunday, October 11th, 2026

View details for race Obstacle Wonderland Hallo-Weird 4 "Relish the Challenge" Adult and Kids Obstacle Course Event

14th Annual Happy Jack 5K

West Nyack, NY

Saturday, October 17th, 2026

View details for race 14th Annual Happy Jack 5K

The Little Guild 13th Annual Run & Wag 5K

Cornwall, CT

Saturday, October 17th, 2026

View details for race The Little Guild 13th Annual Run & Wag 5K

HHNC Meadows & Trails 5K

Cornwall, NY

Saturday, October 17th, 2026

View details for race HHNC Meadows & Trails 5K

EDRRC - Ryan's Run Superhero 5k, Villain 10K an...

Pawling, NY

Saturday, October 17th, 2026

10K

View details for race EDRRC - Ryan's Run Superhero 5k, Villain 10K and Kids (Free) Fun Run.

The Ridgefield Road Fest 50th ANNIVERSARY: 1/2 ...

Ridgefield, CT

Sunday, October 18th, 2026

Half

View details for race The Ridgefield Road Fest 50th ANNIVERSARY: 1/2 Marathon, 7-Miler, & Iris Fund 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

LARC in the Park 5K Run/Walk

Valley Cottage, NY

Sunday, October 18th, 2026

View details for race LARC in the Park 5K Run/Walk

2026 Harry Chapin Memorial Run/Walk Against Hunger

Croton-on-Hudson, NY

Sunday, October 18th, 2026

10K

1 Mile

View details for race 2026 Harry Chapin Memorial Run/Walk Against Hunger

Bristol Mum-A-Thon Road Race 2026

Bristol, CT

Sunday, October 18th, 2026

1 Mile

View details for race Bristol Mum-A-Thon Road Race 2026

Great Pumpkin Classic

TRUMBULL, CT

Sunday, October 18th, 2026

Fast

View details for race Great Pumpkin Classic

Brewster Grin 'N Bear It 5K and 1 Mile Fun Run

Brewster, NY

Saturday, October 24th, 2026

View details for race Brewster Grin 'N Bear It 5K and 1 Mile Fun Run

We Can Be Heroes 5K

Montgomery, NY

Sunday, October 25th, 2026

Fast

View details for race We Can Be Heroes 5K

The Reservoir Run Half Marathon, 5K, Kids Fun R...

WESTON, CT

Sunday, October 25th, 2026

Half

View details for race The Reservoir Run Half Marathon, 5K, Kids Fun Runs & Family Stroll

Collinsville Trick or Trot

Collinsville, CT

Saturday, October 31st, 2026

Trail

View details for race Collinsville Trick or Trot

Leah's 5K Run/Walk And 1K Kids "Spooktacular" F...

Wappingers Falls, NY

Saturday, October 31st, 2026

View details for race Leah's 5K Run/Walk And 1K Kids "Spooktacular" Fun Run

1st Annual To Infinity & Beyond Halloween 5k

Valley Cottage, NY

Saturday, October 31st, 2026

View details for race 1st Annual To Infinity & Beyond Halloween 5k

NAMI Rockland 5K Run / Walk for Mental Wellness...

Valley Cottage, NY

Sunday, November 1st, 2026

View details for race NAMI Rockland 5K Run / Walk for Mental Wellness 2026

Folds of Honor Bethel Veteran's Day 5K

Bethel, CT

Saturday, November 7th, 2026

View details for race Folds of Honor Bethel Veteran's Day 5K

Coach Mike Slinskey Memorial 5k

Wappingers Falls, NY

Sunday, November 8th, 2026

1 Mile

Trail

View details for race Coach Mike Slinskey Memorial 5k

South Orange Family YMCA 5K Turkey Trot

Monroe, NY

Sunday, November 22nd, 2026

View details for race South Orange Family YMCA 5K Turkey Trot

Roxbury Thanksgiving Day Charity Race

Roxbury, CT

Thursday, November 26th, 2026

View details for race Roxbury Thanksgiving Day Charity Race

The Joyce Allen Great Turkey Escape

Redding, CT

Thursday, November 26th, 2026

1 Mile

View details for race The Joyce Allen Great Turkey Escape

Westchester Turkey Trot 10K & 5K presented by N...

Valhalla, NY

Thursday, November 26th, 2026

10K

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

Newtown Turkey Trot

Newtown, CT

Thursday, November 26th, 2026

View details for race Newtown Turkey Trot

Santa Made Me Do It

Bethlehem, CT

Saturday, December 5th, 2026

View details for race Santa Made Me Do It

2026 Jingle Bell Run - Westchester, NY

Purchase, NY

Saturday, December 12th, 2026

View details for race 2026 Jingle Bell Run - Westchester, NY

John Jay Community Trail Race

Cross River, NY

Sunday, April 4th, 2027

Trail

View details for race John Jay Community Trail Race

Stony Point PAL Color Run/Walk 5K & Family Fun ...

Stony Point, NY

Sunday, May 2nd, 2027

View details for race Stony Point PAL Color Run/Walk 5K & Family Fun Event!

Run Like The Wind 5K

Ellenville, NY

Sunday, May 16th, 2027

View details for race Run Like The Wind 5K

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