169 Upcoming 5K Races Near Cheshire, CT

Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Apple Harvest Road Races

Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Run Stanley

Run the Vineyards - Pindar Fall 5K and 8K

Peconic, NY

Sunday, October 4th, 2026

View details for race Run the Vineyards - Pindar Fall 5K and 8K

RACE FOR CATHERINE

Newtown, CT

Friday, October 9th, 2026

View details for race RACE FOR CATHERINE

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Hartland Harvest Run

East Hartland, CT

Saturday, October 10th, 2026

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Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 2026

1 Mile

Trail

View details for race Gemstone Sparkle Sprint 5k

Eversource Hartford Marathon, Half Marathon, Re...

Hartford, CT

Saturday, October 10th, 2026

Marathon

Half

View details for race Eversource Hartford Marathon, Half Marathon, Relay & Charity 5K

Walk/Run for Abilis

Old Greenwich, CT

Sunday, October 11th, 2026

View details for race Walk/Run for Abilis

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.

Tunnel to Towers 5K Run & Walk - Bridgeport, CT

Bridgeport, CT

Saturday, October 17th, 2026

Fast

View details for race Tunnel to Towers 5K Run & Walk - Bridgeport, CT

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 17th, 2026

Trail

View details for race Ivoryton Pumpkin Chase

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

Hope Children's Fund 22nd Annual Larry Hohler B...

Shoreham, NY

Saturday, October 17th, 2026

Trail

View details for race Hope Children's Fund 22nd Annual Larry Hohler Bi-Continental 5k Fun Run/Walk

Harvest Hope 5K

Bolton, CT

Saturday, October 17th, 2026

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Robert Tedford Memorial 5K Road Race

Ellington, CT

Saturday, October 17th, 2026

View details for race Robert Tedford Memorial 5K Road Race

The Big Energy Walk ⚡️ Long Island's 1st ADHD A...

Holtsville, NY

Sunday, October 18th, 2026

View details for race The Big Energy Walk ⚡️ Long Island's 1st ADHD Awareness 5K Walk/Run

2026 Run for The Cove & Memorial Walk

Madison, CT

Sunday, October 18th, 2026

View details for race 2026 Run for The Cove & Memorial Walk

For the 36th time - THE Great Pumpkin Classic

TRUMBULL, CT

Sunday, October 18th, 2026

Fast

View details for race For the 36th time - THE Great Pumpkin Classic

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

Ridgefield, CT

Sunday, October 18th, 2026

Half

Fast

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

Andover Norton Commission Trick or Trot 5K Run/...

Andover, CT

Saturday, October 24th, 2026

View details for race Andover Norton Commission Trick or Trot 5K Run/Walk

Smithtown Running of the Bull

Smithtown, NY

Saturday, October 24th, 2026

Fast

View details for race Smithtown Running of the Bull

Cheshire Community YMCA Harvest Trail Race and ...

Cheshire, CT

Saturday, October 24th, 2026

Trail

View details for race Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

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

Abner Oakes III Veterans Run 5K & 10K

Hamden, CT

Sunday, October 25th, 2026

View details for race Abner Oakes III Veterans Run 5K & 10K

Donny's Dash

Simsbury, CT

Sunday, October 25th, 2026

View details for race Donny's Dash

RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 25th, 2026

Trail

View details for race RACE FOR THE GREENWAY 5K RUN / WALK

Connecticut Law Enforcement Officers Memorial Run

Middletown, CT

Sunday, October 25th, 2026

View details for race Connecticut Law Enforcement Officers Memorial Run

Run The Runway 5K & Kids Fun Run

Meriden, CT

Sunday, October 25th, 2026

View details for race Run The Runway 5K & Kids Fun Run

5K for Ballet!

East Hampton, CT

Sunday, October 25th, 2026

View details for race 5K for Ballet!

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

HKYFS Pumpkin Run 5K, 2M & Kids Run

Higganum, CT

Sunday, October 25th, 2026

Fast

View details for race HKYFS Pumpkin Run 5K, 2M & Kids Run

Collinsville Trick or Trot

Collinsville, CT

Saturday, October 31st, 2026

Trail

View details for race Collinsville Trick or Trot

Lyman Orchards Pie Run

Middlefield, CT

Saturday, October 31st, 2026

View details for race Lyman Orchards Pie Run

15th Annual Milford 5K Trick or Trot Run/Walk

Milford, CT

Saturday, October 31st, 2026

View details for race 15th Annual Milford 5K Trick or Trot Run/Walk

Hamden Hall CISAC League Race

Hamden, CT

Saturday, October 31st, 2026

Trail

View details for race Hamden Hall CISAC League Race

CT Veterans Day Race

Coventry, CT

Saturday, November 7th, 2026

View details for race CT Veterans Day Race

Robert J. Lynes Memorial Road Race

Meriden, CT

Saturday, November 7th, 2026

View details for race Robert J. Lynes Memorial Road Race

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

East Windsor Veterans Day 5K Road Race

Broad Brook, CT

Saturday, November 7th, 2026

View details for race East Windsor Veterans Day 5K Road Race

2026 Colony Grill 'Hot Oil' 5K

Fairfield, CT

Sunday, November 8th, 2026

View details for race 2026 Colony Grill 'Hot Oil' 5K

Husky Run & Ruck 10K, 5K and Fitness Walk

Storrs, CT

Sunday, November 8th, 2026

10K

1 Mile

View details for race Husky Run & Ruck 10K, 5K and Fitness Walk

Hot COCO 5K

Cheshire, CT

Saturday, November 14th, 2026

1 Mile

View details for race Hot COCO 5K

Electric Boat Athletic Club (EBAC) Fall Challenge

New London, CT

Saturday, November 14th, 2026

View details for race Electric Boat Athletic Club (EBAC) Fall Challenge

Waterford High School 14th Annual 5K Turkey Trot

Waterford, CT

Saturday, November 21st, 2026

Fast

View details for race Waterford High School 14th Annual 5K Turkey Trot

Roxbury Thanksgiving Day Charity Race

Roxbury, CT

Thursday, November 26th, 2026

View details for race Roxbury Thanksgiving Day Charity Race

Run Turkey Run! Thanksgiving Day 5K

Hamden, CT

Thursday, November 26th, 2026

View details for race Run Turkey Run! Thanksgiving Day 5K

The Joyce Allen Great Turkey Escape

Redding, CT

Thursday, November 26th, 2026

1 Mile

View details for race The Joyce Allen Great Turkey Escape

Stratford Turkey Day Trot

Stratford, CT

Thursday, November 26th, 2026

Fast

View details for race Stratford Turkey Day Trot

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