169 Upcoming 5K Races Near Cheshire, CT

Groton City Brew Run

Groton, CT

Saturday, September 12th, 2026

View details for race Groton City Brew Run

Paws Crossed 5K!

Yorktown Heights, NY

Saturday, September 12th, 2026

View details for race Paws Crossed 5K!

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

View details for race Run 4 Hunger and Health

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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

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

EDRRC - High Watch Recovery Center's Sprint for...

Kent, CT

Sunday, September 13th, 2026

View details for race EDRRC - High Watch Recovery Center's Sprint for Sobriety 5K Run/Walk

10th Annual ELIH Foundation 5K Family Walk/Run

Riverhead, NY

Sunday, September 13th, 2026

View details for race 10th Annual ELIH Foundation 5K Family Walk/Run

14th Annual Miles for a Mission 5K Run/Walk – I...

Stamford, CT

Monday, September 14th, 2026

View details for race 14th Annual Miles for a Mission 5K Run/Walk – In Person AND Virtual – benefiting INTEMPO

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

Laps For Life 5k

Middletown, CT

Saturday, September 19th, 2026

View details for race Laps For Life 5k

4 Town 5k

Somers, CT

Saturday, September 19th, 2026

View details for race 4 Town 5k

OUTRUN ADDICTION 5K

Enfield, CT

Saturday, September 19th, 2026

View details for race OUTRUN ADDICTION 5K

The Rifleman Run 5k- Run/Walk

Center Moriches, NY

Saturday, September 19th, 2026

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

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

Colby's Path to the Cure 2026

Springfield, MA

Saturday, September 19th, 2026

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

KVIS 2026 Michael Berardino Memorial Road Race

Katonah, NY

Saturday, September 19th, 2026

1 Mile

Trail

View details for race KVIS 2026 Michael Berardino Memorial Road Race

Arc Run

Meriden, CT

Saturday, September 19th, 2026

10K

View details for race Arc Run

Bound for the Sound

Old Lyme, CT

Saturday, September 19th, 2026

10K

1 Mile

Fast

View details for race Bound for the Sound

Come Out & Run 5k

Wilton, CT

Sunday, September 20th, 2026

View details for race Come Out & Run 5k

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

Murray Lender 5K Bagel Run

Woodbridge, CT

Sunday, September 20th, 2026

View details for race Murray Lender 5K Bagel Run

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

MKFD FIRED UP 5K

Mount Kisco, NY

Sunday, September 20th, 2026

View details for race MKFD FIRED UP 5K

Cromwell Riverport 5k

Cromwell, CT

Saturday, September 26th, 2026

View details for race Cromwell Riverport 5k

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.

The River Run

Simsbury, CT

Saturday, September 26th, 2026

10K

1 Mile

View details for race The River Run

Woodbridge 5k

Woodbridge, CT

Saturday, September 26th, 2026

Fast

View details for race Woodbridge 5k

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

2025 Pies & Pub TaTa Trot 5k

Middlebury, CT

Saturday, September 26th, 2026

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

Roxbury Road Race Series #28

Roxbury, CT

Saturday, September 26th, 2026

View details for race Roxbury Road Race Series #28

Chamber Challenge 5K

Meriden, CT

Saturday, September 26th, 2026

View details for race Chamber Challenge 5K

Hayfield Hustle and Oktoberfest at New Pond Far...

Redding, CT

Saturday, September 26th, 2026

Fast

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

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

The 39th Bigelow Tea Community Challenge

Southport, CT

Sunday, September 27th, 2026

1 Mile

View details for race The 39th Bigelow Tea Community Challenge

Bosco Fowler Memorial 5K Road Race

Stafford Springs, CT

Sunday, September 27th, 2026

View details for race Bosco Fowler Memorial 5K Road Race

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

Westover Run the Runway 2026

Chicopee, MA

Saturday, October 3rd, 2026

View details for race Westover Run the Runway 2026

Cider Mill Road Race

Tolland, CT

Saturday, October 3rd, 2026

1 Mile

View details for race Cider Mill Road Race

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

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

Fishbein / YMCA Community Road Race

Wallingford, CT

Sunday, October 4th, 2026

1 Mile

View details for race Fishbein / YMCA Community Road Race

SOLES for All Souls 5K Race/ 2K Walk

Stony Brook, NY

Sunday, October 4th, 2026

View details for race SOLES for All Souls 5K Race/ 2K Walk

Big Sky 5K

Farmington, CT

Sunday, October 4th, 2026

View details for race Big Sky 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

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