Upcoming 5K Races Near Middletown, CT

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Bosco Fowler Memorial 5K Road Race

Stafford Springs, CT

Sunday, September 27th, 2026

View details for race Bosco Fowler Memorial 5K 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

Lisbon Fall Festival Road Race

Lisbon, CT

Sunday, September 27th, 2026

View details for race Lisbon Fall Festival 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

Run/Walk To Save a Life 5K

Hamden, CT

Sunday, September 27th, 2026

View details for race Run/Walk To Save a Life 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

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

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 for the Pumpkins Trail Run

Westerly, RI

Saturday, October 3rd, 2026

10K

Trail

View details for race Run for the Pumpkins Trail Run

Westover Run the Runway 2026

Chicopee, MA

Saturday, October 3rd, 2026

View details for race Westover Run the Runway 2026

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

Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

View details for race Run Stanley

Run the Vineyards - Pindar Fall 5K and 8K

Peconic, NY

Sunday, October 4th, 2026

View details for race Run the Vineyards - Pindar Fall 5K and 8K

RACE FOR CATHERINE

Newtown, CT

Friday, October 9th, 2026

View details for race RACE FOR CATHERINE

Hartland Harvest Run

East Hartland, CT

Saturday, October 10th, 2026

View details for race Hartland Harvest Run

Eversource Hartford Marathon, Half Marathon, Re...

Hartford, CT

Saturday, October 10th, 2026

Marathon

Half

View details for race Eversource Hartford Marathon, Half Marathon, Relay & Charity 5K

Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 2026

1 Mile

Trail

View details for race Gemstone Sparkle Sprint 5k

The Little Guild 13th Annual Run & Wag 5K

Cornwall, CT

Saturday, October 17th, 2026

View details for race The Little Guild 13th Annual Run & Wag 5K

EDRRC - Ryan's Run Superhero 5k, Villain 10K an...

Pawling, NY

Saturday, October 17th, 2026

10K

View details for race EDRRC - Ryan's Run Superhero 5k, Villain 10K and Kids (Free) Fun Run.

Harvest Hope 5K

Bolton, CT

Saturday, October 17th, 2026

View details for race Harvest Hope 5K

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

Bridgeport, CT

Saturday, October 17th, 2026

Fast

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

Hope Children's Fund 22nd Annual Larry Hohler B...

Shoreham, NY

Saturday, October 17th, 2026

Trail

View details for race Hope Children's Fund 22nd Annual Larry Hohler Bi-Continental 5k Fun Run/Walk

Robert Tedford Memorial 5K Road Race

Ellington, CT

Saturday, October 17th, 2026

View details for race Robert Tedford Memorial 5K Road Race

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 17th, 2026

Trail

View details for race Ivoryton Pumpkin Chase

Bristol Mum-A-Thon Road Race 2026

Bristol, CT

Sunday, October 18th, 2026

1 Mile

View details for race Bristol Mum-A-Thon Road Race 2026

33rd Annual Halloween 5K and Kids Fun Run

Brookfield, CT

Sunday, October 18th, 2026

View details for race 33rd Annual Halloween 5K and Kids Fun Run

The Ridgefield Road Fest 50th ANNIVERSARY: 1/2 ...

Ridgefield, CT

Sunday, October 18th, 2026

Half

Fast

View details for race The Ridgefield Road Fest 50th ANNIVERSARY: 1/2 Marathon, 7-Miler, & Iris Fund 5K

Great Pumpkin Classic

TRUMBULL, CT

Sunday, October 18th, 2026

Fast

View details for race Great Pumpkin Classic

The Ludlow Clocktower Classic 5k

Ludlow, MA

Saturday, October 24th, 2026

View details for race The Ludlow Clocktower Classic 5k

Mt. Tom Trail Race

Holyoke, MA

Saturday, October 24th, 2026

10K

View details for race Mt. Tom Trail Race

Cheshire Community YMCA Harvest Trail Race and ...

Cheshire, CT

Saturday, October 24th, 2026

Trail

View details for race Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Donny's Dash

Simsbury, CT

Sunday, October 25th, 2026

View details for race Donny's Dash

5K for Ballet!

East Hampton, CT

Sunday, October 25th, 2026

View details for race 5K for Ballet!

Abner Oakes III Veterans Run 5K & 10K

Hamden, CT

Sunday, October 25th, 2026

View details for race Abner Oakes III Veterans Run 5K & 10K

The Reservoir Run Half Marathon, 5K, Kids Fun R...

WESTON, CT

Sunday, October 25th, 2026

Half

View details for race The Reservoir Run Half Marathon, 5K, Kids Fun Runs & Family Stroll

RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 25th, 2026

Trail

View details for race RACE FOR THE GREENWAY 5K RUN / WALK

Run The Runway 5K & Kids Fun Run

Meriden, CT

Sunday, October 25th, 2026

View details for race Run The Runway 5K & Kids Fun Run

2026 CT LEO Memorial Run

Middletown, CT

Sunday, October 25th, 2026

View details for race 2026 CT LEO Memorial Run

St. Michael School 5K Turkey Trot

Pawcatuck, CT

Saturday, October 31st, 2026

1 Mile

View details for race St. Michael School 5K Turkey Trot

Lyman Orchards Pie Run

Middlefield, CT

Saturday, October 31st, 2026

View details for race Lyman Orchards Pie Run

15th Annual Milford 5K Trick or Trot Run/Walk

Milford, CT

Saturday, October 31st, 2026

View details for race 15th Annual Milford 5K Trick or Trot Run/Walk

Collinsville Trick or Trot

Collinsville, CT

Saturday, October 31st, 2026

Trail

View details for race Collinsville Trick or Trot

Hamden Hall CISAC League Race

Hamden, CT

Saturday, October 31st, 2026

Trail

View details for race Hamden Hall CISAC League Race

Folds of Honor Bethel Veteran's Day 5K

Bethel, CT

Saturday, November 7th, 2026

View details for race Folds of Honor Bethel Veteran's Day 5K

Robert J. Lynes Memorial Road Race

Meriden, CT

Saturday, November 7th, 2026

View details for race Robert J. Lynes Memorial Road Race

CT Veterans Day Race

Coventry, CT

Saturday, November 7th, 2026

View details for race CT Veterans Day Race

Plainfield Salute the Troops 5k, Fun Run, & Sol...

Central Village, CT

Saturday, November 7th, 2026

1 Mile

View details for race Plainfield Salute the Troops 5k, Fun Run, & Soldier Stroll

East Windsor Veterans Day 5K Road Race

Broad Brook, CT

Saturday, November 7th, 2026

View details for race East Windsor Veterans Day 5K Road Race

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