169 Upcoming 5K Races Near Cheshire, CT

Milford Road Runners Independence Day 5K

Milford, CT

Saturday, July 4th, 2026

View details for race Milford Road Runners Independence Day 5K

EDRRC - Racing to Save Lives 5K/10K

Lagrangeville, NY

Sunday, July 5th, 2026

10K

Trail

View details for race EDRRC - Racing to Save Lives 5K/10K

East Shore 5k

New Haven, CT

Sunday, July 5th, 2026

View details for race East Shore 5k

Rails to Trails

East Hampton, CT

Friday, July 10th, 2026

Fast

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Roxbury Road Race Series #18

Roxbury, CT

Saturday, July 11th, 2026

Trail

View details for race Roxbury Road Race Series #18

Smile Like Jack 5k/10k/Fun Run

East Otis, MA

Saturday, July 11th, 2026

10K

Trail

View details for race Smile Like Jack 5k/10k/Fun Run

Point O' Woods Beach 5K Run/Walk

Old Lyme, CT

Saturday, July 11th, 2026

View details for race Point O' Woods Beach 5K Run/Walk

Enfield 4th of July 5k

Enfield, CT

Saturday, July 11th, 2026

View details for race Enfield 4th of July 5k

Petit Family Foundation 5K

Plainville, CT

Sunday, July 12th, 2026

View details for race Petit Family Foundation 5K

Ambulance Driver 5K ...

Derby, CT

Wednesday, July 15th, 2026

View details for race Ambulance Driver 5K at BADSONS Brewery

THE FAIRFIELD POLICE SUNSET 5K - Presented by M...

Fairfield, CT

Wednesday, July 15th, 2026

View details for race THE FAIRFIELD POLICE SUNSET 5K - Presented by Moneco Advisors

Bubble Run | Hartford 2026

Hartford, CT

Saturday, July 18th, 2026

View details for race Bubble Run | Hartford 2026

LYSB Midsummer Run

Old Lyme, CT

Saturday, July 25th, 2026

Fast

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Southwest Cafe Margarita 5K

Ridgefield, CT

Saturday, July 25th, 2026

View details for race Southwest Cafe Margarita 5K

New Milford Parks & Recreation Road Race

New Milford, CT

Saturday, July 25th, 2026

View details for race New Milford Parks & Recreation Road Race

Valley of Hartford 5K Road Race

Newington, CT

Saturday, July 25th, 2026

View details for race Valley of Hartford 5K Road Race

Woodmont 5K

Milford, CT

Saturday, July 25th, 2026

View details for race Woodmont 5K

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

View details for race Run the Vineyards - Pindar Vineyards 5K

Jordan's Run Veterans' Memorial 5K Run/Walk

Sag Harbor, NY

Sunday, July 26th, 2026

View details for race Jordan's Run Veterans' Memorial 5K Run/Walk

Surfin' Santa's Christmas In July 5k & Holiday ...

Stratford, CT

Sunday, July 26th, 2026

1 Mile

View details for race Surfin' Santa's Christmas In July 5k & Holiday Stroll

The Trumbull Rotary Sunset 5k Run & Walk

Trumbull, CT

Friday, July 31st, 2026

1 Mile

View details for race The Trumbull Rotary Sunset 5k Run & Walk

It's All Downhill From Here 5K

Wilton, CT

Saturday, August 1st, 2026

Trail

View details for race It's All Downhill From Here 5K

Boys & Girls Club of Milford Ice Cream Run (5K)

Milford, CT

Sunday, August 2nd, 2026

View details for race Boys & Girls Club of Milford Ice Cream Run (5K)

The Perogie Dash

Danbury, CT

Saturday, August 8th, 2026

View details for race The Perogie Dash

2026 Natchaug 5K Color Run & Walk

Mansfield Center, CT

Saturday, August 8th, 2026

View details for race 2026 Natchaug 5K Color Run & Walk

Follow Natural Fitness Women's Health 5K

Bridgeport, CT

Saturday, August 8th, 2026

1 Mile

View details for race Follow Natural Fitness Women's Health 5K

5th Annual Mentoring Matters 5K

Springfield, MA

Saturday, August 8th, 2026

View details for race 5th Annual Mentoring Matters 5K

Run for Wishes 5K Benefitting MAKE-A-WISH® CONN...

Stratford, CT

Sunday, August 9th, 2026

View details for race Run for Wishes 5K Benefitting MAKE-A-WISH® CONNECTICUT

Run the Vineyards - Priam Vineyards 5K

Colchester, CT

Sunday, August 9th, 2026

View details for race Run the Vineyards - Priam Vineyards 5K

Jill's Race for MS

Beacon Falls, CT

Saturday, August 15th, 2026

View details for race Jill's Race for MS

MAD 5K

New London, CT

Saturday, August 15th, 2026

View details for race MAD 5K

Millbrook Vineyards Wine Run 5k

Millbrook, NY

Sunday, August 16th, 2026

1 Mile

View details for race Millbrook Vineyards Wine Run 5k

Guess Your Time 2.5 mile Race

Yorktown Heights, NY

Wednesday, August 19th, 2026

View details for race Guess Your Time 2.5 mile Race

Amber Room Run from the Sun 5K

Danbury, CT

Thursday, August 20th, 2026

View details for race Amber Room Run from the Sun 5K

PATH TO THE PARADE 5K

Hamden, CT

Friday, August 21st, 2026

Trail

Fast

View details for race PATH TO THE PARADE 5K

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

Shore 2 The Pour Beach Run 2026

Stratford, CT

Saturday, August 22nd, 2026

Trail

View details for race Shore 2 The Pour Beach Run 2026

Old Wethersfield 5K & 10K

Wethersfield, CT

Sunday, August 23rd, 2026

10K

View details for race Old Wethersfield 5K & 10K

2026 Unite to Fight 5K Run/Walk

Stamford, CT

Sunday, August 23rd, 2026

View details for race 2026 Unite to Fight 5K Run/Walk

Sgt Scoulars Overdose Awareness and Recovery 5K...

New Milford, CT

Saturday, August 29th, 2026

Fast

View details for race Sgt Scoulars Overdose Awareness and Recovery 5K Run

Be Happy Road Race

Ellington, CT

Sunday, August 30th, 2026

10K

View details for race Be Happy Road Race

Newtown Community Running Event

Newtown, CT

Sunday, August 30th, 2026

10K

Half

View details for race Newtown Community Running Event

Lobster Loop 5K

Canton, CT

Sunday, August 30th, 2026

View details for race Lobster Loop 5K

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

Ring of Fire 5K

Northville, NY

Saturday, September 5th, 2026

View details for race Ring of Fire 5K

Haddam Neck Fair 5K

Haddam, CT

Sunday, September 6th, 2026

View details for race Haddam Neck Fair 5K

3rd Annual LSC Soccer Stride

Ledyard, CT

Sunday, September 6th, 2026

View details for race 3rd Annual LSC Soccer Stride

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

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