Upcoming Races Near Pleasant Valley, NY

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Roxbury Road Race Series #30

Roxbury, CT

Saturday, October 10th, 2026

View details for race Roxbury Road Race Series #30

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 "The Clock i...

Wallkill, NY

Sunday, October 11th, 2026

View details for race Obstacle Wonderland Hallo-Weird 4 "The Clock is Ticking" Adult and Kids OCR event

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 17th, 2026

Trail

View details for race Tom Centinaro Memorial "Dam" Race

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

Roxbury Road Race Series #31

Roxbury, CT

Saturday, October 17th, 2026

View details for race Roxbury Road Race Series #31

14th Annual Happy Jack 5K

West Nyack, NY

Saturday, October 17th, 2026

View details for race 14th Annual Happy Jack 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.

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

The 36th edition of THE Great Pumpkin Classic

TRUMBULL, CT

Sunday, October 18th, 2026

View details for race The 36th edition of THE Great Pumpkin Classic

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

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

Rockland Road Runners Turkey Trot Training Prog...

Valley Cottage, NY

Sunday, October 18th, 2026

View details for race Rockland Road Runners Turkey Trot Training Program for The Marisa Fund

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

2nd Annual Brewster Grin 'N Bear It 5K and 1 Mi...

Brewster, NY

Saturday, October 24th, 2026

View details for race 2nd Annual Brewster Grin 'N Bear It 5K and 1 Mile Fun Run

Roxbury Road Race Series #32

Roxbury, CT

Saturday, October 24th, 2026

View details for race Roxbury Road Race Series #32

Kiwanis Club of Newburgh Scholarship Run

Newburgh, NY

Sunday, October 25th, 2026

Trail

View details for race Kiwanis Club of Newburgh Scholarship Run

FALL Run The Farm

Katonah, NY

Sunday, October 25th, 2026

1 Mile

Trail

View details for race FALL Run The Farm

Crosby Sports Hall of Fame Fall into Fall 4k

Waterbury, CT

Sunday, October 25th, 2026

View details for race Crosby Sports Hall of Fame Fall into Fall 4k

We Can Be Heroes 5K

Montgomery, NY

Sunday, October 25th, 2026

Fast

View details for race We Can Be Heroes 5K

Reservoir Run Half Marathon, 5K, Kids Fun Runs ...

WESTON, CT

Sunday, October 25th, 2026

Half

View details for race 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

Roxbury Road Race Series #33

Roxbury, CT

Saturday, October 31st, 2026

View details for race Roxbury Road Race Series #33

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

Raven Events

Cross River, NY

Sunday, November 1st, 2026

10K

Trail

View details for race Raven Events

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

Pocantico Hills Races

Tarrytown, NY

Saturday, November 7th, 2026

Marathon

Half

Trail

View details for race Pocantico Hills Races

Roxbury Road Race Series #34

Roxbury, CT

Saturday, November 7th, 2026

View details for race Roxbury Road Race Series #34

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

Roxbury Fall Classic

Roxbury, CT

Saturday, November 14th, 2026

Half

Marathon

Ultra

View details for race Roxbury Fall Classic

Hillacious Half Marathon

Litchfield, CT

Saturday, November 14th, 2026

Half

10K

View details for race Hillacious Half Marathon

Roxbury Road Race Series #35

Roxbury, CT

Saturday, November 21st, 2026

Trail

View details for race Roxbury Road Race Series #35

South Orange Family YMCA 5K Turkey Trot

Monroe, NY

Sunday, November 22nd, 2026

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

EDRRC - Beer Mile

Pawling, NY

Sunday, November 22nd, 2026

1 Mile

View details for race EDRRC - Beer Mile

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

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

Roxbury Road Race Series #36

Roxbury, CT

Saturday, November 28th, 2026

View details for race Roxbury Road Race Series #36

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

Roxbury Road Race Series Season Pass

Roxbury, CT

Thursday, December 31st, 2026

View details for race Roxbury Road Race Series Season Pass

Brookfield Lions Run for Sight 4-Miler

Brookfield, CT

Friday, January 1st, 2027

Fast

View details for race Brookfield Lions Run for Sight 4-Miler

HTC Winter Series Barkhamsted 8.5/17 mile

Barkhamsted, CT

Sunday, January 10th, 2027

View details for race HTC Winter Series Barkhamsted 8.5/17 mile

42nd Annual Lake Waramaug Polar Bear Run

Warren, CT

Sunday, February 28th, 2027

View details for race 42nd Annual Lake Waramaug Polar Bear Run

John Jay Community Trail Race

Cross River, NY

Sunday, April 4th, 2027

Trail

View details for race John Jay Community Trail Race

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