Upcoming 5K Races Near Chester, CT

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5th Annual Purple Light Project 5K

Hartford, CT

Saturday, October 3rd, 2026

1 Mile

Fast

View details for race 5th Annual Purple Light Project 5K

Run for the Pumpkins Trail Run

Westerly, RI

Saturday, October 3rd, 2026

10K

Trail

View details for race Run for the Pumpkins Trail Run

Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Apple Harvest Road Races

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

Hartland Harvest Run

East Hartland, CT

Saturday, October 10th, 2026

View details for race Hartland Harvest Run

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

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 17th, 2026

Trail

View details for race Ivoryton Pumpkin Chase

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

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

Harvest Hope 5K

Bolton, CT

Saturday, October 17th, 2026

View details for race Harvest Hope 5K

Robert Tedford Memorial 5K Road Race

Ellington, CT

Saturday, October 17th, 2026

View details for race Robert Tedford Memorial 5K Road Race

34th Annual Halloween 5K and Kids Fun Run

Brookfield, CT

Sunday, October 18th, 2026

View details for race 34th Annual Halloween 5K and Kids 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

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

Run The Runway 5K & Kids Fun Run

Meriden, CT

Sunday, October 25th, 2026

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

2026 CT LEO Memorial Run

Middletown, CT

Sunday, October 25th, 2026

View details for race 2026 CT LEO Memorial Run

Donny's Dash

Simsbury, CT

Sunday, October 25th, 2026

View details for race Donny's Dash

Abner Oakes III Veterans Run 5K & 10K

Hamden, CT

Sunday, October 25th, 2026

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

5K for Ballet!

East Hampton, CT

Sunday, October 25th, 2026

View details for race 5K for Ballet!

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

Collinsville Trick or Trot

Collinsville, CT

Saturday, October 31st, 2026

Trail

View details for race Collinsville Trick or Trot

St. Michael School 5K Turkey Trot

Pawcatuck, CT

Saturday, October 31st, 2026

1 Mile

View details for race St. Michael School 5K Turkey Trot

Hamden Hall CISAC League Race

Hamden, CT

Saturday, October 31st, 2026

Trail

View details for race Hamden Hall CISAC League Race

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

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

Pawtuxet River 5k: Run of the Mills

Coventry, RI

Saturday, November 7th, 2026

Trail

View details for race Pawtuxet River 5k: Run of the Mills

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

CT Veterans Day Race

Coventry, CT

Saturday, November 7th, 2026

View details for race CT Veterans Day Race

Plainfield Salute the Troops 5k, Fun Run, & Sol...

Central Village, CT

Saturday, November 7th, 2026

1 Mile

View details for race Plainfield Salute the Troops 5k, Fun Run, & Soldier Stroll

Robert J. Lynes Memorial Road Race

Meriden, CT

Saturday, November 7th, 2026

View details for race Robert J. Lynes Memorial Road Race

2026 Colony Grill 'Hot Oil' 5K

Fairfield, CT

Sunday, November 8th, 2026

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

Centerville Bank Thompson Turkey Trot

Thompson, CT

Sunday, November 8th, 2026

Trail

View details for race Centerville Bank Thompson Turkey Trot

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

Stonington Vineyards Wine Run Turkey Trot 5k

Stonington, CT

Sunday, November 8th, 2026

Trail

View details for race Stonington Vineyards Wine Run Turkey Trot 5k

Monson Memorial Classic Half Marathon & 5K

Monson, MA

Sunday, November 8th, 2026

Half

Fast

View details for race Monson Memorial Classic Half Marathon & 5K

Hot COCO 5K

Cheshire, CT

Saturday, November 14th, 2026

1 Mile

View details for race Hot COCO 5K

Waterford High School 14th Annual 5K Turkey Trot

Waterford, CT

Saturday, November 21st, 2026

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

Stratford Turkey Day Trot

Stratford, CT

Thursday, November 26th, 2026

Fast

View details for race Stratford Turkey Day Trot

Newtown Turkey Trot

Newtown, CT

Thursday, November 26th, 2026

View details for race Newtown Turkey Trot

Branford Thanksgiving 5K

Branford, CT

Thursday, November 26th, 2026

Fast

View details for race Branford Thanksgiving 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

Run Turkey Run! Thanksgiving Day 5K

Hamden, CT

Thursday, November 26th, 2026

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

Norwich Winterfest 5K

Norwich, CT

Saturday, December 5th, 2026

View details for race Norwich Winterfest 5K

Santa Made Me Do It

Bethlehem, CT

Saturday, December 5th, 2026

View details for race Santa Made Me Do It

CLA Blue Back Mitten Run

West Hartford, CT

Sunday, December 6th, 2026

View details for race CLA Blue Back Mitten Run

Niantic Jingle 5k

Niantic, CT

Saturday, December 12th, 2026

View details for race Niantic Jingle 5k

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