Upcoming 5K Races Near Chester, CT

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52nd Annual Rooster Run

Newtown, CT

Saturday, June 13th, 2026

10K

View details for race 52nd Annual Rooster Run

6th Annual A. W. Stanley Park 5K

New Britain, CT

Saturday, June 13th, 2026

1 Mile

10K

View details for race 6th Annual A. W. Stanley Park 5K

Fleet Feet Hartford Summer 2026 5k & 10k Traini...

West Hartford, CT

Saturday, June 13th, 2026

10K

View details for race Fleet Feet Hartford Summer 2026 5k & 10k Training Programs

Red, White and Blue in Bethany 5K

Bethany, CT

Saturday, June 13th, 2026

View details for race Red, White and Blue in Bethany 5K

Flag Day 5K

Bethel, CT

Sunday, June 14th, 2026

View details for race Flag Day 5K

Whoopie Pie Waddle

Springfield, MA

Sunday, June 14th, 2026

1 Mile

View details for race Whoopie Pie Waddle

Devil Dash 5k

Stratford, CT

Sunday, June 14th, 2026

View details for race Devil Dash 5k

Milford Rotary Run in the Park 5K

Milford, CT

Sunday, June 14th, 2026

View details for race Milford Rotary Run in the Park 5K

Run For The Rock

Bridgeport, CT

Sunday, June 14th, 2026

View details for race Run For The Rock

Solstice Sprint 5K

West Hartford, CT

Wednesday, June 17th, 2026

Trail

Fast

View details for race Solstice Sprint 5K

Beacon of Hope 5k

Montauk, NY

Saturday, June 20th, 2026

View details for race Beacon of Hope 5k

2026 Rushford’s Race for Recovery 5K Color Run

Portland, CT

Saturday, June 20th, 2026

View details for race 2026 Rushford’s Race for Recovery 5K Color Run

4th Annual Bloomfield Juneteenth 5K

Bloomfield, CT

Saturday, June 20th, 2026

View details for race 4th Annual Bloomfield Juneteenth 5K

3rd Annual LSC Soccer Stride

Ledyard, CT

Saturday, June 20th, 2026

View details for race 3rd Annual LSC Soccer Stride

46th Annual Springfield JCC Father's Day Road Race

Springfield, MA

Sunday, June 21st, 2026

10K

1 Mile

View details for race 46th Annual Springfield JCC Father's Day Road Race

8th Annual 5k Walk/Run for Overdose Awareness

Shelton, CT

Thursday, June 25th, 2026

View details for race 8th Annual 5k Walk/Run for Overdose Awareness

The Club 2nd Annual 5k!

Naugatuck, CT

Saturday, June 27th, 2026

View details for race The Club 2nd Annual 5k!

Rose Arts Road Race

Norwich, CT

Saturday, June 27th, 2026

10K

View details for race Rose Arts Road Race

11th Annual Milford Moves for Veterans 5K

Milford, CT

Sunday, June 28th, 2026

View details for race 11th Annual Milford Moves for Veterans 5K

GRR Firecracker 5K Presented By Highland Park M...

Glastonbury, CT

Sunday, June 28th, 2026

View details for race GRR Firecracker 5K Presented By Highland Park Market

Tunnel to Towers 5K Run & Walk - Bethel, CT

Bethel, CT

Sunday, June 28th, 2026

Fast

View details for race Tunnel to Towers 5K Run & Walk - Bethel, CT

Milford Road Runners Independence Day 5K

Milford, CT

Saturday, July 4th, 2026

View details for race Milford Road Runners Independence Day 5K

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

View details for race Rails to Trails

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

Roxbury Road Race Series #18

Roxbury, CT

Saturday, July 11th, 2026

View details for race Roxbury Road Race Series #18

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

5K Training Program for the Battle of Stonington

Mystic, CT

Thursday, July 16th, 2026

View details for race 5K Training Program for the Battle of Stonington

Run For Ryan Memorial Run

Dayville, CT

Saturday, July 18th, 2026

View details for race Run For Ryan Memorial Run

Bubble Run | Hartford 2026

Hartford, CT

Saturday, July 18th, 2026

View details for race Bubble Run | Hartford 2026

Blessing of the Fleet-Stonington 5K Road Race a...

Stonington, CT

Thursday, July 23rd, 2026

View details for race Blessing of the Fleet-Stonington 5K Road Race and 2 Mile Walk

Woodmont 5K

Milford, CT

Saturday, July 25th, 2026

View details for race Woodmont 5K

Valley of Hartford 5K Road Race

Newington, CT

Saturday, July 25th, 2026

View details for race Valley of Hartford 5K Road Race

LYSB Midsummer Run

Old Lyme, CT

Saturday, July 25th, 2026

Fast

View details for race LYSB Midsummer Run

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

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)

Race of Hope Southampton

Southampton, NY

Sunday, August 2nd, 2026

View details for race Race of Hope Southampton

Stonington Cross Country 5K

Pawcatuck, CT

Wednesday, August 5th, 2026

View details for race Stonington Cross Country 5K

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

2025 Natchaug Stop the Stigma 5K Color Run & Walk

Mansfield Center, CT

Saturday, August 8th, 2026

View details for race 2025 Natchaug Stop the Stigma 5K Color Run & Walk

5th Annual Mentoring Matters 5K

Springfield, MA

Saturday, August 8th, 2026

View details for race 5th Annual Mentoring Matters 5K

Run the Vineyards - Priam Vineyards 5K

Colchester, CT

Sunday, August 9th, 2026

View details for race Run the Vineyards - Priam Vineyards 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

Jill's Race for MS

Beacon Falls, CT

Saturday, August 15th, 2026

View details for race Jill's Race for MS

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