Upcoming 5K Races Near South Windsor, CT

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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 Goat Track Club XC Classic

Sutton, MA

Sunday, August 23rd, 2026

View details for race Old Goat Track Club XC Classic

Old Wethersfield 5K & 10K

Wethersfield, CT

Sunday, August 23rd, 2026

10K

View details for race Old Wethersfield 5K & 10K

Stride For Change: Supporting Our Veterans and ...

Holyoke, MA

Saturday, August 29th, 2026

View details for race Stride For Change: Supporting Our Veterans and Military Families

1st Annual Newtown Community Running Event

Newtown, CT

Sunday, August 30th, 2026

10K

Half

View details for race 1st Annual Newtown Community Running Event

Lobster Loop 5K

Canton, CT

Sunday, August 30th, 2026

View details for race Lobster Loop 5K

Be Happy Road Race

Ellington, CT

Sunday, August 30th, 2026

10K

View details for race Be Happy Road Race

Run for The Hills

Niantic, CT

Saturday, September 5th, 2026

Trail

View details for race Run for The Hills

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

View details for race Haddam Neck Fair 5K

Faxon Law New Haven Road Race

New Haven, CT

Monday, September 7th, 2026

Half

View details for race Faxon Law New Haven Road Race

Kailey Jaie Prenoveau Scholarship 5K Run

Harwinton, CT

Saturday, September 12th, 2026

View details for race Kailey Jaie Prenoveau Scholarship 5K Run

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

Run 4 Hunger and Health

Newtown, CT

Saturday, September 12th, 2026

1 Mile

View details for race Run 4 Hunger and Health

Groton City Brew Run

Groton, CT

Saturday, September 12th, 2026

View details for race Groton City Brew 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

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

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

4 Town 5k

Somers, CT

Saturday, September 19th, 2026

View details for race 4 Town 5k

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

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

OUTRUN ADDICTION 5K

Enfield, CT

Saturday, September 19th, 2026

View details for race OUTRUN ADDICTION 5K

2026 Run To The River 5K

Deep River, CT

Saturday, September 19th, 2026

View details for race 2026 Run To The River 5K

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

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

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

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.

Chamber Challenge 5K

Meriden, CT

Saturday, September 26th, 2026

View details for race Chamber Challenge 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

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

View details for race The River Run

The Alianza 5K: Cider Donut Dash

Holyoke, MA

Saturday, September 26th, 2026

View details for race The Alianza 5K: Cider Donut Dash

2026 Pies & Pub TaTa Trot 5k

Middlebury, CT

Saturday, September 26th, 2026

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

4th Annual Beach to Beach 5k

Morris, CT

Sunday, September 27th, 2026

Fast

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

Bosco Fowler Memorial 5K Road Race

Stafford Springs, CT

Sunday, September 27th, 2026

View details for race Bosco Fowler Memorial 5K Road Race

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

Pounding the Pavement for Pink Races

Seymour, CT

Friday, October 2nd, 2026

1 Mile

View details for race Pounding the Pavement for Pink Races

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

Westover Run the Runway 2026

Chicopee, MA

Saturday, October 3rd, 2026

View details for race Westover Run the Runway 2026

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

Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Run Stanley

Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Apple Harvest Road Races

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

Sheriff's Shuffle 5k Run Walk

Holyoke, MA

Sunday, October 4th, 2026

1 Mile

View details for race Sheriff's Shuffle 5k Run Walk

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