Upcoming 5K Races Near Middletown, CT

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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

2026 Camp Jewell 5K Fun Run/Walk & Kids 1M

Colebrook, CT

Saturday, June 20th, 2026

1 Mile

Trail

View details for race 2026 Camp Jewell 5K Fun Run/Walk & Kids 1M

4th Annual Bloomfield Juneteenth 5K

Bloomfield, CT

Saturday, June 20th, 2026

View details for race 4th Annual Bloomfield Juneteenth 5K

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!

EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

View details for race EDRRC - Pawling Moonlight Trail Run 5K

Rose Arts Road Race

Norwich, CT

Saturday, June 27th, 2026

10K

View details for race Rose Arts Road Race

Westport Road Runners Summer Series

Westport, CT

Saturday, June 27th, 2026

1 Mile

15K

View details for race Westport Road Runners Summer Series

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

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

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

4th Annual Christmas in July Tree.1 Walk and Ru...

Sturbridge, MA

Saturday, July 11th, 2026

View details for race 4th Annual Christmas in July Tree.1 Walk and Run for Fun

Enfield 4th of July 5k

Enfield, CT

Saturday, July 11th, 2026

View details for race Enfield 4th of July 5k

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

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

Knights of Columbus Scholarship 5k

Wilbraham, MA

Sunday, July 19th, 2026

View details for race Knights of Columbus Scholarship 5k

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

LYSB Midsummer Run

Old Lyme, CT

Saturday, July 25th, 2026

Fast

View details for race LYSB Midsummer Run

Southwest Cafe Margarita 5K

Ridgefield, CT

Saturday, July 25th, 2026

View details for race Southwest Cafe Margarita 5K

Valley of Hartford 5K Road Race

Newington, CT

Saturday, July 25th, 2026

View details for race Valley of Hartford 5K Road Race

New Milford Parks & Recreation Road Race

New Milford, CT

Saturday, July 25th, 2026

View details for race New Milford Parks & Recreation Road Race

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

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

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

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

Race of Hope Southampton

Southampton, NY

Sunday, August 2nd, 2026

View details for race Race of Hope Southampton

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)

Stonington Cross Country 5K

Pawcatuck, CT

Wednesday, August 5th, 2026

View details for race Stonington Cross Country 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 powered by Best...

Springfield, MA

Saturday, August 8th, 2026

View details for race 5th Annual Mentoring Matters 5K powered by Best Fitness

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

MAD 5K

New London, CT

Saturday, August 15th, 2026

View details for race MAD 5K

Jill's Race for MS

Beacon Falls, CT

Saturday, August 15th, 2026

View details for race Jill's Race for MS

Brimfield Wine Run 5k

Brimfield, MA

Saturday, August 15th, 2026

View details for race Brimfield Wine Run 5k

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