Upcoming 5K Races Near Chester, CT

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MAD 5K

New London, CT

Saturday, August 15th, 2026

View details for race MAD 5K

Battle of Stonington 5K

Stonington, CT

Tuesday, August 18th, 2026

Fast

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PATH TO THE PARADE 5K

Hamden, CT

Friday, August 21st, 2026

Trail

Fast

View details for race PATH TO THE PARADE 5K

Shore 2 The Pour Beach Run 2026

Stratford, CT

Saturday, August 22nd, 2026

View details for race Shore 2 The Pour Beach Run 2026

17th Annual Saybrook Point 5k Road Race 2026

Old Saybrook, CT

Saturday, August 22nd, 2026

View details for race 17th Annual Saybrook Point 5k Road Race 2026

Old Wethersfield 5K & 10K

Wethersfield, CT

Sunday, August 23rd, 2026

10K

View details for race Old Wethersfield 5K & 10K

Be Happy Road Race

Ellington, CT

Sunday, August 30th, 2026

10K

View details for race Be Happy Road Race

Lobster Loop 5K

Canton, CT

Sunday, August 30th, 2026

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1st Annual Newtown Community Running Event

Newtown, CT

Sunday, August 30th, 2026

10K

Half

View details for race 1st Annual Newtown Community Running Event

Ring of Fire 5K

Northville, NY

Saturday, September 5th, 2026

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Run for The Hills

Niantic, CT

Saturday, September 5th, 2026

Trail

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Black Hog Brewing Co. 5K Road Race

Oxford, CT

Saturday, September 5th, 2026

View details for race Black Hog Brewing Co. 5K Road Race

Haddam Neck Fair 5K

Haddam, CT

Sunday, September 6th, 2026

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Faxon Law New Haven Road Race

New Haven, CT

Monday, September 7th, 2026

Half

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Groton City Brew Run

Groton, CT

Saturday, September 12th, 2026

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SUFFIELD PARKS & RECREATION ROAD RACE

Suffield, CT

Saturday, September 12th, 2026

View details for race SUFFIELD PARKS & RECREATION ROAD RACE

Springfield Puerto Rican Parade Pa’lante 5K Run...

Springfield, MA

Saturday, September 12th, 2026

View details for race Springfield Puerto Rican Parade Pa’lante 5K Run/Walk

ESM Touchdown Booster Color/Fun Run

Manorville, NY

Saturday, September 12th, 2026

View details for race ESM Touchdown Booster Color/Fun Run

Kailey Jaie Prenoveau Scholarship 5K Run

Harwinton, CT

Saturday, September 12th, 2026

View details for race Kailey Jaie Prenoveau Scholarship 5K Run

Run 4 Hunger and Health

Newtown, CT

Saturday, September 12th, 2026

1 Mile

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Montville Race Day 5K , 10K , and Color Run

Oakdale, CT

Sunday, September 13th, 2026

10K

View details for race Montville Race Day 5K , 10K , and Color Run

PTSMC Stride to Provide 5K Run/Walk

Wallingford, CT

Sunday, September 13th, 2026

View details for race PTSMC Stride to Provide 5K Run/Walk

Charlie Stavros Memorial Beach Run

Westerly, RI

Tuesday, September 15th, 2026

View details for race Charlie Stavros Memorial Beach Run

Colby's Path to the Cure 2026

Springfield, MA

Saturday, September 19th, 2026

View details for race Colby's Path to the Cure 2026

Bozrah Fire Department 5k Road Race and Kids' f...

Bozrah, CT

Saturday, September 19th, 2026

View details for race Bozrah Fire Department 5k Road Race and Kids' fun run

2026 Run To The River 5K

Deep River, CT

Saturday, September 19th, 2026

View details for race 2026 Run To The River 5K

OUTRUN ADDICTION 5K

Enfield, CT

Saturday, September 19th, 2026

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Arc Run

Meriden, CT

Saturday, September 19th, 2026

10K

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Bound for the Sound

Old Lyme, CT

Saturday, September 19th, 2026

10K

1 Mile

Fast

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2nd Annual PCS Harvest Hustle 5K & Kids Run

Pomfret Center, CT

Saturday, September 19th, 2026

Trail

View details for race 2nd Annual PCS Harvest Hustle 5K & Kids Run

4 Town 5k

Somers, CT

Saturday, September 19th, 2026

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Christina's House Annual 5K Run or 1 Mile Walk

Springfield, MA

Saturday, September 19th, 2026

View details for race Christina's House Annual 5K Run or 1 Mile Walk

The Rifleman Run 5k- Run/Walk

Center Moriches, NY

Saturday, September 19th, 2026

View details for race The Rifleman Run 5k- Run/Walk

17th Annual Farmington River Run 5K Trail Race

Farmington, CT

Sunday, September 20th, 2026

Trail

View details for race 17th Annual Farmington River Run 5K Trail Race

Murray Lender 5K Bagel Run

Woodbridge, CT

Sunday, September 20th, 2026

View details for race Murray Lender 5K Bagel Run

Roxbury Road Race Series #28

Roxbury, CT

Saturday, September 26th, 2026

View details for race Roxbury Road Race Series #28

The River Run

Simsbury, CT

Saturday, September 26th, 2026

10K

1 Mile

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New Pond Farm Hayfield Hustle

Redding, CT

Saturday, September 26th, 2026

Fast

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2026 Pies & Pub TaTa Trot 5k

Middlebury, CT

Saturday, September 26th, 2026

View details for race 2026 Pies & Pub TaTa Trot 5k

Cromwell Riverport 5k

Cromwell, CT

Saturday, September 26th, 2026

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Chamber Challenge 5K

Meriden, CT

Saturday, September 26th, 2026

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Come on Over 5K and 2.1 Mile Fitness Walk

Portland, CT

Saturday, September 26th, 2026

1 Mile

View details for race Come on Over 5K and 2.1 Mile Fitness Walk

Sickle Cell Disease Association of America, CT/...

New Haven, CT

Saturday, September 26th, 2026

1 Mile

View details for race Sickle Cell Disease Association of America, CT/ Michelle's House Walk. Run. Bike.

4th Annual Beach to Beach 5k

Morris, CT

Sunday, September 27th, 2026

Fast

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

The 39th Bigelow Tea Community Challenge

Southport, CT

Sunday, September 27th, 2026

1 Mile

View details for race The 39th Bigelow Tea Community Challenge

Run/Walk To Save a Life 5K

Hamden, CT

Sunday, September 27th, 2026

View details for race Run/Walk To Save a Life 5K

Lisbon Fall Festival Road Race

Lisbon, CT

Sunday, September 27th, 2026

View details for race Lisbon Fall Festival Road Race

Bosco Fowler Memorial 5K Road Race

Stafford Springs, CT

Sunday, September 27th, 2026

View details for race Bosco Fowler Memorial 5K Road Race

Pounding the Pavement for Pink Races

Seymour, CT

Friday, October 2nd, 2026

1 Mile

View details for race Pounding the Pavement for Pink Races

Running for Water for Africa 5K

Milford, CT

Saturday, October 3rd, 2026

1 Mile

Fast

View details for race Running for Water for Africa 5K

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